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The Perfect Tuscany Road Trip Itinerary (+ Driving Tips!)

Planning the perfect Tuscany road trip itinerary is no easy feat–but it’s well worth getting right.

If you’re dreaming of delicious Italian food, of romantic sunsets and Tuscan wines, of rolling hills peppered with vineyards as far as the eye can see, of hilltop villages and of Renaissance art, this Tuscany itinerary has you covered.

We’ve put this ultimate guide to planning a Tuscany road trip after spending several months traveling in the region over a period of years, often on road trips.

We’ve explored Tuscany by car, train, and tour, in large multigenerational family groups and as a couple, in tiny towns and in the fabulous cities of Florence and Siena.

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We’ve visited museums, gone horseback riding, zipped along countryside roads on a Vespa, and taken quiet strolls down deserted country lanes. We’ve taken food tours and wine tours, and stopped at more than our fair share of vineyards and restaurants independently, too.

Suffice it to say, we absolutely adore traveling in Tuscany, and this Tuscany itinerary is put together based on our detailed experiences traveling in the region as well as additional research.

We want to help you plan your perfect Tuscany road trip itinerary, especially if it’s your first time in the region.

Here’s what we suggest.

Table of Contents

How We Structured This Tuscany Road Trip Itinerary

How long will this tuscany itinerary take, getting around during your tuscany road trip, will this tuscany itinerary work without a car, the ultimate tuscany road trip itinerary, other destinations to add to your tuscany road trip itinerary, tuscany road trip itinerary map, the best time to visit tuscany, useful travel tips for driving in tuscany, what to pack for your tuscany road trip.

We structured this Tuscany road trip itinerary as a loop beginning and ending in Florence.

It’s designed primarily for first-time visitors to the region who want to soak up the classic Tuscany experience: think rolling hills, golden light, scrumptious wine, picturesque hilltop villages, and some of the best food you’ve ever eaten in your life.

… But that being said, even longtime lovers of Tuscany will find something for them here (just ask our extended family).

With this Tuscany itinerary, you’ll visit some of the most iconic places in the region, while also peppering in stops at smaller towns and attractions that would likely go unnoticed if you stuck to exploring via train.

Is it a cop-out to say that this Tuscany road trip will take as long as you have?

Perhaps, but whether you have 5 days in Tuscany, a week in Tuscany, or a month in Tuscany, this circular route will provide an excellent backbone to your Tuscany road trip.

If your trip is short–say 5 days in Tuscany or less–you’ll be able to shorten your stays in some towns (in a pinch, for example, Pisa and Lucca can be combined into one day), and with a longer trip to Tuscany, you’ll have a chance to adopt a leisurely pace and add in more excursions like wine tasting or days spent at one of Tuscany’s saunas.

Ideally, I would say that this Tuscany road trip would be spread across roughly 10 days to 2 weeks in Tuscany, but of course, that won’t always be possible–especially if you want to see more regions of Italy during your trip!

If you do have a longer trip to Tuscany planned, we recommend taking a look at some of the additional Tuscany road trip destinations that we’ve outlined below the main itinerary and seeing what other spots catch your eye.

For most people, of course, taking a Tuscany road trip will require renting a car.

We’ll cover some tips and tricks for renting a car here below the Tuscany itinerary (or you can use the table of contents section at the bottom of the introduction to this Tuscany travel blog post to navigate there!), but here’s the short version: we recommend renting a small car in Tuscany through Discover Cars , which will allow you to compare prices and inclusions of multiple companies at the same time and choose the best car for you from there.

We also recommend renting your car only after you leave Florence, which we’ll cover a bit more below, so you likely won’t need one for every day of your trip to Tuscany!

Check rates & book your rental car with Discover Cars today!

Short answer? Yes, it can.

Through a combination of trains, buses, and carefully selected guided tours (we recommend several reputable ones in our Things to Do in Florence post ), this Tuscany itinerary can be completed without a car, though the logistics will be challenging in certain places.

That being said, there’s something very special about taking a Tuscany road trip, and by not driving, you will lose out on the charm of seeing some of the smaller towns at night, miss some of the prettiest vistas, and have a little less freedom in planning your trip.

However, we completely understand that not everyone planning a Tuscany itinerary can or would like to drive, and we fully believe you can have a deeply fulfilling trip to Tuscany without a car–we’ve done it several times ourselves.

And, while you will lose some freedom, you’ll also gain a bit of peace of mind, as driving in Tuscany is certainly not the most carefree driving in the world!

Start your Tuscany itinerary in Florence.

As the capital of Tuscany, Cradle of the Renaissance, and home to the biggest airport (and train station) in the region, there’s no better place to start your Tuscany itinerary than in Florence.

Ideally, we recommend a minimum of two full days here, which will give you enough time to explore all of the major sights.

Marvel at the art in the Uffizi Gallery, soak in the views from Piazzale Michelangelo and more, (window)shop for gold jewelry on the Ponte Vecchio, eat your way through Mercato Centrale, stand in awe of the Duomo, and visit Michelangelo’s masterpiece David in the Galleria dell’Accademia.

We’ve created several guides to Florence based on our six weeks or so spent exploring the city, including a one-day itinerary and a two-day itinerary , so be sure to check those out for more detail.

For this Tuscany road trip itinerary in particular, though, we have a crucial piece of advice regarding driving: don’t pick up your rental car until the morning you leave Florence.

Having a rental car while in the city is not only unnecessary, it’s an absolute burden. Driving in Florence’s historic city center is extremely limited, and you’ll save both money and headaches by ditching the car until you’re ready to hit the countryside.

Where to Stay in Florence

B&B Le Stanze del Duomo  — Though Florence hotels can be a bit pricey and stretch the definition of “budget”, B&B Le Stanze’s beautiful rooms and impeccable location in Florence will be sure to have you swooning!

Check rates & book your stay at B&B Le Stanze del Duomo!

Bargello Guest House  — Located in the heart of Florence, this property is only a short (read: less than 5-minute) walk away from some of Florence’s highlights like the Palazzo Vecchio. Staying here, you’ll be within easy walking distance of the best of what Florence has to offer.

Check rates & book your stay at Bargello Guest House!

Hotel Lungarno  — Nestled right against the Arno River and home to one of the best views of the Ponte Vecchio in Florence (not to mention some of the best views of the rest of Florence from their top deck), Hotel Lungarno is our personal “if we ever  really  want to splurge” hotel in Florence. You can’t go wrong using Hotel Lungarno as your base for one day in Florence!

Check rates & book your stay at Hotel Lungarno!

Start your Tuscany road trip and drive to Lucca.

Laidback and charming, colorful Lucca is the perfect first stop on your Tuscany road trip and an excellent place to grow accustomed to the ins and outs of driving and parking in Tuscan towns.

Lucca is not too big, not too small, and parking is fairly easy to find right outside the city walls.

It also happens to be a gorgeous, relaxing city that is a fantastic place to soak up the ambiance of Tuscany.

While you’re there, be sure to check out the beautiful Piazza dell’Anfiteatro, which, like Siena’s main piazza, is actually an oval rather than a traditional square, and to stroll along the tops of the city’s 16th-century fortifying walls, which are completely accessible to the public.

Don’t miss a climb up Torre Guinigi, either–not only does it boast incredible views of Lucca, but it’s home to several oak trees that are growing in the sky!

Stop by Pisa.

I’ll be perfectly honest: of all the places we recommend or mention in this Tuscany itinerary, Pisa is the one I’m least in a hurry to get back to.

It’s generally far more crowded than most of these other destinations–even the very touristy ones–and outside of Pisa’s famous tower and surrounding historic complex, the town is not exactly known as one of the most beautiful or interesting Tuscan villages.

It is, however, incredibly famous, and the Leaning Tower of Pisa itself more than lives up to expectations. The Leaning Tower of Pisa is truly stunning, and far more opulent and beautiful in person than I expected before laying eyes on it for the first time.

If you’d like to see it, we recommend stopping by for half a day on your Tuscan road trip, checking out the tower itself as well as the nearby Duomo and baptistery, and then moving on.

If you’d like to tour the interior of any of the structures, including climbing to the top of the leaning tower, we absolutely recommend booking skip-the-line tickets in advance .

Book your skip-the-line tickets to visit the Leaning Tower of Pisa now!

Make your way to San Gimignano.

Known for its stunning towers (14 of an original 72 remain), long history of wealth due to its prime location along a Roman trading route, gorgeous city center, beautiful views, and convenient location that is roughly equidistant from Siena and Florence, it’s safe to say that San Gimignano is both incredibly popular and well worth visiting.

We adore this beautiful hilltop town, and highly recommend spending at least one night either in town or nearby if you can, in order to enjoy the city without the crowds of day-trippers that tend to take over the streets during the day.

Don’t forget to make time in your schedule for a scoop (or several scoops, let’s be real) of gelato from the world-famous Gelateria Dondoli: as one of the best-known and most acclaimed gelato shops in Italy, it’s a safe bet that whatever you order is bound to impress.

Head to Siena.

While today Florence is significantly better-known than Siena, that was not always the case: beautiful Siena was once the military rival of Florence, and the history of the Middle Ages in the region is dotted with stories of their back-and-forth battles.

Today, Siena is known for its Palio di Siena horse race that takes place bi-annually in the oval-shaped Piazza del Campo–when you stand in the middle of the piazza, be sure to picture 20 horses running at full-speed around a packed crowd–it’s truly impressive.

Siena is packed full of interesting things to do: it’s home to arguably the most beautiful Duomo in Tuscany (don’t forget to check out the Piccolomini Library while you’re in there!), and we absolutely recommend taking the Porta di Cielo, aka Gate to Heaven, tour of the cathedral’s roof if you can–it’s magnificent.

At least once during your trip, climb to the top of one of Siena’s monuments for an epic view–the Torre del Mangia in Piazza del Campo is a popular choice, but personally, we love that the view from the top of the Opera della Metropolitana includes stunning views of the Piazza del Campo from a bit of a distance.

Spend some time in Val d’Orcia and soak up the Tuscan countryside.

Of all the scenic places in Tuscany, Val d’Orcia might just be the most beautiful of them all.

This UNESCO-recognized valley is home to the Tuscan road trip views of your fantasies, and it truly has to be seen to be believed.

If you have the time in your Tuscany itinerary, we recommend booking at least a couple of nights in a nearby country villa or agriturismo in order to slowly savor the beauty of the region, but if not, even an afternoon drive here is well worth the trip out.

Marvel at the beauty of Montepulciano.

Tiny, gorgeous, and home to arguably some of the best countryside views of all the villages in Tuscany, it’s impossible not to be charmed by stunning Montepulciano–and that’s even before you start sipping its world-famous wine.

While it doesn’t take terribly long to explore a village this size on your Tuscany road trip, Montepulciano has one of those peaceful atmospheres that you just want to savor.

While you’re there, be sure to stop by the beautiful Piazza Grande, admire views of the nearby Church of San Biagio that is located just outside of town, and to taste the local wine, vino nobile di Montepulciano .

Pay a visit to Arezzo.

As you turn back north toward Florence to start to wind down your Tuscany road trip, be sure to check out the beautiful city of Arezzo.

Often overlooked on Tuscany road trips, Arezzo is a delightful city that is well worth the time it takes to visit.

Home to Roman ruins (including the remains of Arezzo’s very own Colosseum), sweeping views of the countryside from the Medici fortress, some impressively well-preserved fifteenth-century frescoes, and a large number of antique shops just waiting to be perused, Arezzo is an excellent addition to any Tuscany itinerary.

Be sure not to miss a chance to climb the clock tower at Palazzo della Fraternita dei Laici right off the main square (Piazza Grande)–the views from the top are absolutely sublime, and it is our personal favorite spot in Arezzo.

Drive back to Florence & say goodbye to Tuscany.

As your Tuscany road trip winds to a close, head back to Florence to drop off your car, say goodbye, and–depending on time–perhaps visit one or two more sights in the Cradle of the Renaissance as well.

While we’ve set up this Tuscany itinerary to act as a loop, if you’re going to be flying out of Italy (or continuing your Italy travels outside of Tuscany) in a different location, you can also consider dropping off your car in Rome, Milan, Bologna, or even Venice–but keep in mind that you will likely incur a one-way drop-off fee for doing so, so be sure to budget for that if needed!

While this Tuscany road trip itinerary gives a solid outline of the region and is a delightful trip all on its own, for those with a bit of extra time in the area (or those who like to move at a very fast pace), there is an unlimited number of additional destinations you could add to your trip, both in Tuscany and in its surrounding regions of Umbria, Emilia-Romagna, and Liguria.

We’ve outlined a few of each here to give you some ideas as you plan your trip to Tuscany!

Within Tuscany

The most famous of all of Tuscany’s hot springs has emerged from comparative obscurity into being a full-blown famous photography location in recent years, but there’s no doubt that it’s still a dream to visit–if you have time during your Tuscany road trip to make the trek out there and you’re a fan of hot springs, it’s definitely worth a visit.

Dating back to the Etruscan period and nestled on a hill high above the sweeping Tuscan landscapes it overlooks, the walled city of Volterra is absolutely worth visiting as part of your Tuscan road trip itinerary.

The ease of accessing it paired with its beauty make this one of the first towns we would recommend if you are looking for additional stops along your road trip in Tuscany.

Cortona is perhaps best known for the famous book/movie that is based there, but even without the fame brought by Under the Tuscan Sun , this tiny Tuscan town is still a fabulous place to visit!

I’ll be honest: a trip to Elba is a bit of a stretch for all but the longest trips to Tuscany, but it bears mentioning simply for the fact that Elba is Tuscany’s very own island–and “Mediterranean island” is just not what you normally associate with a trip to Tuscany.

Whether you want to scuba dive, enjoy delicious seafood, lounge on the beach, or chase down the island’s interesting history (Elba was the first place Napoleon was exiled to, though he escaped a little under a year later), there’s no doubt that Elba makes a unique addition to any Tuscany itinerary.

Easier to access than Elba but equally focused on all things coastal, the seaside city of Livorno is the perfect Tuscany road trip destination for anyone looking to enjoy a little sea and sun as part of their trip to Tuscany.

Best known for its delicious Brunello di Montalcino wine, the hilltop town of Montalcino is a delightful slice of Tuscany that is easy to access from Siena and Val d’Orcia.

Outside of Tuscany

Cinque terre.

Of all destinations outside of Tuscany that people tend to be eager to add onto their Tuscany trip, Cinque Terre almost always falls near the top.

We’ve visited this sensational collection of Ligurian fishing villages twice as part of a Tuscany road trip, as well as on a standalone visit, and we can attest that they are well worth the trouble if you have time in your itinerary.

We absolutely do not recommend driving into the villages, however–instead, drive to the train station at La Spezia or Levanto, park your car, and then take the train into the villages from there.

Known, above all else, for its food, Bologna is the perfect location for foodies to flock to if they’re looking for some truly epic cuisine during their road trip.

Bologna is the capital of Emilia-Romagna, the region that is home to so many of the things us foreigners tend to associate with Italian food: tagliatelle al ragu (aka spaghetti bolognese), mortadella (aka bologna), parmigiano-reggiano , traditional balsamic vinegar, and more.

Once you get done eating, Bologna has plenty of other sights to explore, as well–but the food alone is worth visiting for.

Set on a hilltop overlooking sweeping views of the Umbrian countryside, Orvieto is as historical as it is picturesque: dating back to the Etruscans and once (briefly) the home of the pope, whether you’re looking to dive deep into the history, enjoy the tasty Orvieto Classico wine, or simply admire the magnificent vistas, Orvieto has something to offer.

We adore this little village–be sure to check out the Duomo, the views from the Torre del Moro, and the underground while you’re there, among plenty of other fun things to do.

As the location of the birth, work, and death of St. Francis, Assisi is an enormously popular pilgrim destination among Catholic travelers–but even if you’re not Catholic, this small Umbrian town has plenty of history and beauty to offer.

St. Francis was the founder of the Franciscan Order–a name you’ll see pop up a lot in Italy–and is also one of the patron saints of the country.

In Assisi, you can tour the enormously impressive Basilica of St. Francis while learning about the life and history of the saint.

Take This Map With You! Click each highlight to pull up the name of the destination. To save this map to “Your Places” on Google Maps, click the star to the right of the title. You’ll then be able to find it under the Maps tab of your Google Maps account! To open the map in a new window, click the button on the top right of the map.

Ultimately, Tuscany is a beautiful destination year-round, and you can never go wrong with a visit.

Spring in Tuscany brings beautiful flowers but plenty of rain, summer brings lots of tourists but also long days and sunshine.

Fall brings the harvest and temperamental weather, and winter brings cold, gray weather but also low prices and a distinct lack of crowds.

If you ask us, though, our favorite time to take a Tuscany road trip will always be in the fall, particularly late September through mid-October.

True, it’s hardly offseason (in other words, there will be plenty of other tourists around), and there’s a good chance of experiencing a cold and/or rainy day or two–but the changing colors across the countryside, the incredible food that is freshly harvested, and the crisp chill that sweeps through the air each evening as the heat dies down for the year give the region a magical quality that we will never tire of experiencing.

We’ve spent at least part of the last few autumns in Tuscany, and we see no reason to stop that tradition anytime soon.

While driving in Tuscany is not the most difficult driving you’ll encounter in Italy (looking at you, Rome and Sicily), it definitely has its quirks!

Here are a few tips we recommend keeping in mind as you plan your Tuscany road trip itinerary.

Make sure you have access to a GPS for your Tuscany road trip.

This is absolutely imperative, in our opinion, and can make the difference between an insanely stressful Tuscany road trip and a fairly laid-back one: whether you purchase an international cell phone plan through your carrier before leaving for Tuscany or you purchase an Italian SIM card on the ground, you’ll 100% want to make sure you have cell phone data–and therefore GPS–with you as you drive.

Shop around for your rental car.

I’m almost 100% certain that we’ve used a different rental car company every time we’ve rented a car in Italy–that’s how much the prices can vary depending on your time of travel, pickup and dropoff locations, size of the vehicle, and more.

We recommend searching for your car via Discover Car Hire , which will allow you to check out the rates of several different rental car agencies in Tuscany at once and compare prices and inclusions side-by-side.

Shop for your Tuscnay rental car with Discover Car Hire today!

Buy the insurance–you won’t regret it.

Ultimately, this is up to you–I know some people prefer not to buy additional CDW insurance (aka the insurance that covers damages to the actual car you’re driving, as opposed to your liability to anyone else) on trips–but we buy it every. single. time. in Tuscany and have no regrets.

I don’t want to overstate things, because driving in Tuscany isn’t exactly like driving in the Wild West–but let’s just say that the roads are often tiny, the buildings very close, the parking lots cramped, and the other tourists’ rental cars parked nearby are frequently scratched and dinged in a way that while not horrendously damaging, is definitely something a car rental company would love to charge you for if it happened on your watch.

The peace of mind is absolutely worth it to us–you can price it for yourself when shopping on Discover Car Hire , or purchase a travel insurance policy through that includes car rental insurance (but be sure to double-check the policy, because only some policies cover it).

You need an international driving permit to rent a car in Tuscany.

Technically, you always need an international driving permit to rent a car in Italy, and that includes in Tuscany.

You can pick this up before you leave home from AAA, and it’s very easy and cheap to do–just a bit annoying, as it’s one more thing to add to your to-do list before leaving for your Tuscany road trip.

Now, that being said–will your rental agency always ask for it? No. Will the police always ask for it? No.

Is it worth the risk of being refused a rental car or getting a ticket over $25 USD and a bit of hassle? Not in my opinion.

Rent the smallest car possible.

Not only is it cheaper, which is always excellent, but a smaller car in Tuscany is also much easier to drive.

While the highways in Tuscany are pretty standard, this-could-be-anywhere highways, the small country roads, parking lots near villages, and dirt roads leading to vineyards and villas can be incredibly narrow–which, naturally, does not stop them from being used for two-way traffic (you’ll probably end up pulling over to let someone maneuver past you at least a couple of times during your Tuscany road trip).

Be sure to account for how much space you’ll need for luggage, especially if you have three or more people in your group, but other than that–the smaller, the better.

If you get a ticket, you probably won’t know it right away.

Traffic citations in Tuscany are generally captured via camera, so if you get one, you probably won’t know it right away.

Instead, your license plate will be captured, the ticket will be sent to the owner of the car (ie, your rental company), and then your rental company will forward it onto you.

Unfortunately, that means you won’t be 100% sure you didn’t have any infractions during your Tuscany road trip until several weeks after you get home.

You will encounter toll roads in Tuscany–so carry cash.

Most toll roads in Tuscany will accept credit cards, but it’s always best to have small bills/coins of cash on you–just in case you run into a cash-only booth (or you need a last-minute coffee and/or gelato, which are also very important parts of any Tuscany road trip itinerary).

Be prepared to park and then climb up to towns.

Tuscany is known for its delightful hilltop towns, full of winding, narrow streets and plenty of foot traffic.

Combine the above description of Tuscany that we all know and love with the very concept of a Tuscany road trip, and an obvious question emerges: where are the cars?

Usually, they’re in parking garages built literally under the hilltop towns or on the outskirts of historical centers… which means you often have to walk up steep hills in order to reach the center.

Some cities, like Siena, have escalators installed to help alleviate this problem–but in general, be prepared for a little bit of a leg workout when visiting small towns in Tuscany!

Avoid ZTL zones like the plague.

Essentially, ZTL zones are restricted access zones that dot most of Italy’s historic city centers, including in Tuscany.

If you drive into one, even accidentally, you’re risking a big ticket (and we’ve definitely had to call tiny Tuscan police stations to help some of our family members pay them off months after the fact).

Avoid them by parking on the outskirts of historical centers and by doing your research ahead of time, which leads me to…

Whenever possible, figure out where you’re going to park next before leaving.

This is one of our favorite tricks to keeping stress levels down when driving into a new town in Tuscany: know where the public parking lots are and, when heading out for the day, put your directions on for that particular spot rather than just the town.

This will absolutely cut down on the risk of accidentally driving into a ZTL zone (and therefore getting a ticket), and also make the trip into town much less stressful.

Now, in the interest of full disclosure, this doesn’t always work–occasionally the parking lot you have picked out will be full, or you’ll luck out and find street parking along the way–but in general, it will definitely make your life easier during your Tuscany road trip.

Travel Insurance  — We don’t ever suggest traveling without travel insurance–anything can happen, and this is definitely a case of better safe than sorry. We use and recommend  Safety Wing for trips to Tuscany.

International Driving Permit — If you’re coming from outside the EU and plan to rent a car in Tuscany, you’ll need to make sure to acquire an International Driving Permit in your home country, before  coming to Italy.

It is required for all car rentals in Italy, and while the rental company may not ask, it’s not worth the risk of being refused a car once you arrive or getting a fine if you’re pulled over to be without one. Play it safe and if you plan to drive during your trip, add getting an International Driving Permit to your pre-Tuscany planning!

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About Kate Storm

In May 2016, I left my suburban life in the USA and became a full-time traveler. Since then, I have visited 50+ countries on 5 continents and lived in Portugal, developing a special love of traveling in Europe (especially Italy) along the way. Today, along with my husband Jeremy and dog Ranger, I’m working toward my eventual goal of splitting my life between Europe and the USA.

67 thoughts on “The Perfect Tuscany Road Trip Itinerary (+ Driving Tips!)”

I love this website It has convinced my husband and me to go on a driving tour of italy! I actually have a question. How do you know or find out where is the ZTL zones so you can avoid them? Thanks! Ilene

So glad to hear that, Ilene! Hope you guys have a great time!

Your GPS can help you avoid the ZTL zones, but the biggest thing is paying very close attention to the signs, as they’ll be marked there. As a general rule, historic centers of cities are ZTL zones, so it’s safest to avoid those entirely and park outside the center before walking into the town!

Hi Kate, Do you have any recommendations for accommodations on the Tuscan itinerary? We would be going in Sept 2022.

Hi Sabrina!

Yes, absolutely. We have several properties linked in this post, but if you’re looking for specific towns/cities, we also have recommendations in each of our independent city guides.

Hello, You guys look like you have a great life! My husband and I are older than you but have retired a bit early so we can travel while we are still able to move about. We have traveled quite a bit independently throughout the years so we are comfortable going to new places. Your blog is great and has so much useful information. Thank you for putting all of your knowledge out there. I know it’s a lot of work to do so. If you don’t mind me asking…we were told you have to have a permanent address at least 6 months out of the year for tax purposes. How do you get around that? Don’t mean to overstep. Thanks!

Thank you so much, Joanne! We really appreciate it. 🙂 Residency requirements vary by state, but we maintain a technical permanent address in our home state of Oklahoma where we pay our taxes, maintain our businesses, keep our driver’s licenses up to date, etc. Most nomadic travelers have a similar setup for logistical purposes!

Hello, thanks so much for this post. It’s so helpful! My partner and I are going to copy this for our holiday in June this year. I was just wondering if you could tell me which towns you stayed overnight in? Grazie, Olivia

So glad it was helpful, Olivia! Where to spend the night really depends on your specific taste, but from this itinerary, we’ve stayed overnight in Florence, Siena, and Arezzo. We’ve also stayed in countryside villas near the Val d’Orcia and Lucca.

Since you’ll be driving, we 100% recommend staying in the country at least once–Tuscan villas and agriturismos are absolutely amazing. For staying in the towns themselves, make sure your hotels have parking, but other than that, any and all of them make a great place to spend the night.

My daughter and I just booked a rental car for our trip to Tuscany this summer thanks to your post. I was nervous about driving but you laid it all out perfectly, thank you. We’re going for her graduation present and it’ll be the first time in Italy for us both. Bookmarking your site now for when the trip gets closer. Thanks again!

That’s amazing to hear, thank you Susan! Comments like this never fail to make my day, we are ALL about making sure your trip goes perfectly! Hope you guys have a fantastic time, and congratulations to your daughter on her graduation!

Hey, this has been quite useful. Im planning my road trip, but im going clockwise on this route. Since i live in The Netherlands, i will drive in from the north, Florence and start here and after Pisa-Lucca, the last stop instead of heading back to Florence is Cinque Terre, to enjoy a bit of the coast. I will take the advice of leaving the car in La Spezia, but if you had to choose to spend a night in Cinque Terre, which woudl you guys recommend, Vernazza or Manarola?

Glad to hear it, thanks Rodolfo!

Which village is best for spending the night in Cinque Terre is definitely a matter of preference, and Vernazza and Manarola happen to be two of my top 3 favorites (the other is Riomaggiore). You can’t go wrong with either, but I’d recommend Vernazza if you’re looking for something smaller, and Manarola if you want to have access to a wider variety of shops and restaurants. Manarola is a more popular (read: crowded) sunset spot, but both places will quiet down considerably once the day trippers head home.

Wonderful, informative article! I am so glad I found your website. We are hoping to be able to visit Tuscany in summer 2022. Italy is our favourite country, but we haven’t been to Tuscany or Cinque Terre, so I really appreciate the wealth of information on your website!

Thank you so much, Cheryl! So glad to hear that. 🙂 Hope you guys have an amazing trip to Tuscany and Cinque Terre!

Hi! I just came upon your site when doing a search for info on an upcoming trip. My husband and I are planning a trip for the end of Oct. We will be renting a car in Florence, spending about two days driving through Tuscany and returning the rental in Rome. I know that’s way too short to do Tuscany justice, but we have a commitment in Venice prior to Florence, and are bookended with a fixed return date from Rome. Where in Florence would be our best choice to rent a car so we can get on the road to Tuscany easily? Same question for returning rental in Rome without having to deal with city driving. Lastly, we are doing some basic research in Tuscany in order to maybe get a place there down the road. Should we consider spending our two nights there in Lucca? Thanks so much and I will definitely be following your adventures!

Hi Rohini! There are so many places to rent cars in both cities it’s really impossible to say–I’d keep an eye out for the best deal and then look carefully at the directions. Unfortunately, some city driving is probably unavoidable if you want to make it all the way from Florence to Rome, but you can limit it based on your schedule.

If you’re just going to relax, Lucca is a great choice! If you want to compare possible areas to own a property in Tuscany though, I’d probably recommend one night there and one night in the Val d’Orcia area. You may also want to consider a look at Siena, depending on whether you want to be close to a city or not.

Hi Kate. Thanks for your quick response! This is very helpful info. I had read somewhere that Tiburtina station in Rome is a good spot for rental return since it would not involve going into the city to return. Would you say that is the case? Once again, thank you for your help!

Hi guys, I imagine you’ve had some ups and downs in your travel in the last 2 years because of Covid. I really hope you’ve been able to stay safe and still continue some of your adventures. I found your site and am really keen to follow your path around Tuscany when my husband and I go this year. I looked up your destinations and would really encourage you to look into coming to Australia and New Zealand some time if you can. Down Under is a wonderful place and New Zealand has just about everything you could ever want to see in a really small country! Thank you for your really helpful and informative site. Take care.

Yes, there have been many ups and downs over the last couple of years for sure, but luckily things are mostly up right now! We’ve decided to base ourselves in Portugal for the next little bit to enjoy lots of Europe throughout 2022. 🙂 Knock on wood, but hopefully our next Tuscan road trip is just around the corner!

We’d love to head down to Aus and New Zealand one day! No plans at the moment, but you never know. 🙂

Hope you guys have a wonderful trip!

Such a great and helpful Itinerary, thank you!

We’re planning to visit late September and I am nervous about the driving portion – what location would you recommend for pick up, outside of Florence? We’re hoping to get a drive to our first destination (open to anywhere) and then pick up a car – appreciate any extra tips you might have! I was surprised to not see any mention of Greve as a stop, have you been? This was what I thought was my main stop in Tuscany but I am now rethinking everything! 😀 We have 5 nights in Tuscany (counted Florence separately as a stop when we head North) and prefer to not spend too much time in the city and want to visit many wineries and enjoy the local food! If you have any very specific favorite wineries to stay at or places to dine, I would love to hear about them!

Thanks again for such a detailed post! I have a lot to consider 🙂

Thanks so much, Cait!

There’s never enough time for all the towns, lol, but if you want to swap in Greve you absolutely can! We haven’t been ourselves yet but generally speaking there’s no such thing as a “wrong” Tuscan town to visit. 😉

If you want to pick up a car outside of Florence, I’d recommend taking a look at Siena. By the time you get into the very small hilltop towns like San Gimignano, etc, there may not be car rental agencies available (or if they are, it’ll just be an office and they’ll need to drive the car itself to you from a bigger city–which often comes with a fee).

Have an amazing trip!

Hi, I am planning a vacation trip to Rome (5 days) and from there a road trip (5 days) to the Tuscan area. I’ve been already to Florence and Pisa. I will like to know cities or towns with good food and scenery off the beaten path. Thanks so much for your time and sharing your knowledge.

It depends on how you define off the beaten path, but just about everywhere in Tuscany is further off the path than Florence and Pisa! And virtually everywhere in Tuscany has great food. 🙂

Arezzo, Volterra, Pienza, Montepulciano are all delightful, some more commonly visited than others. Montalcino is tiny but beautiful.

We also love Lucca, it’s much quieter in many ways than Florence or Siena.

A common theme is that if you spend the night in any of these places, they will get much more peaceful and quiet if you spend the night, as the day-trippers will head home.

Some of the spa towns other than Saturnia can feel off the beaten path, such as Bagno Vignoni. They’re popular, but more catered to tourists from nearby.

Wonderful article – thanks!

Planning Sept trip – 4 days Rome, 2 days Florence, 3 days Venice (as of now)

Considering adding a Tuscany component but limited to time. Any suggestions to condensing to 2-3 days as a loop or feasibility of starting in Florence and ending in Venice?

Any input greatly appreciated.

Happy to help, Richard!

With a 2-3 day driving loop from Florence, I’d recommend driving to either the Val d’Orcia (so towns like Montalcino and Pienza) or a nearby base like Montepulciano, and then basing yourself there for a couple of days. You can drive between a handful of close-together towns, see the landscape, enjoy an agriturismo, do some wine tastings, etc, all within a close distance.

Driving from Florence to Venice isn’t a go-to suggestion of mine since you don’t need a car in either city, but we’ve actually made the drive ourselves as part of a family trip and it was lovely! Bologna, Ferrara, and/or Padua are easy stops right along the route.

If you wanted to take a couple of days between the two cities, a loop through Parma, Modena, Reggio-Emilio and Bologna would put you in the heart of Emilia-Romagna, which is the origin of some of the most beloved Italian foods (traditional balsamic, parmigiano-reggiano, etc).

It’s not the most efficient way to get from Florence to Venice of course (that’d be the high-speed train), but if you want to make a trip of it, you’ll have fun!

If you do want to consider renting a car in Florence and dropping it off in Venice, though, be sure to ask your rental company if they allow it and what fees they would charge before making any plans.

One of my stops is in Luca and the hotel and parking garage are in the Atlantic. How do I get a permit to drive through it.

I think you may have a typo in there, but I’m assuming you mean you have a hotel booked in the historic center of Lucca? If the hotel offers private parking on-site, you can give them your license plate number and they’ll be able to make arrangements for you.

If they don’t have parking, you’ll likely need to park outside the walls and walk into the center to reach your hotel.

Hope that helps!

The parking os not on-site but within the walls.

So you are saying that all I need to do is call either the garage or hotel with my rental car license number and they would be able to get me a permit to drive inside the walled city to get to the hotel and garage?

In your case, I’d contact the hotel and ask where they recommend you park, and then if you head to the garage inside the walls, look at the map to confirm the directions to access it.

Essentially, your goal is to avoid the ZTL zones, which trigger an automatic ticket (and technically two–one for entering the zone and one for leaving it). Unfortunately, since all of the traffic controls are done by camera, you’ll have no sure way of knowing at the time you park if you’ve crossed the boundary.

The public parking within the walls should have a way to access it without passing through a ZTL zone, the concern is taking a wrong turn, etc. If you do need to pass through a ZTL zone (generally speaking in Italy), hotels within the walls can get access for their guests but I’m not sure if yours can since they don’t have on-site parking. These rules also vary from city to city in Italy.

Generally speaking, in the case that you do get access to a ZTL zone to access hotel parking (I know yours doesn’t have it, but just generally), you won’t get a paper permit or anything like that. It’s all done by license plate and camera.

Hi Kate! What an insightful article. I am planning a trip to Itlay in August for 12 days with a girlfriend who has never been to Italy. We are landing in Rome, spending 3 days there, and making our way to Florence by train. We will have 6 days in the Tuscany region and plan to rent a car after reading your article. This is what I am planning for our road trip and what your feedback. Would love to know if you can recommend an amazing winery with meals and wine tasting at one of our stops. I have taken suggestions from your blog on places to see and things to do at each stop:) Am I packing in too much? Day 1 – Florence to Lucca to San Gimignano spend the night here Day 2 – San Gimignano to Siena to Val D’Orcia spend 1 or 2 nights here Day 3 or 4 – Val d’orcia to Montepulciano to Montalcino (not sure about Montalcino) Day 4 – Drive to Saturnia from the last destination and head back to Florence

Hi Gira! All of the places you have mentioned are wonderful, but yes, I’d highly recommend cutting a few places from your list in order to savor the others more!

Driving, parking, walking into historic centers, etc, all eat up quite a bit of time.

I’m assuming you’re planning a couple of days in Florence on days 5-6. Ideally, I’d recommend only changing your “base” one other time. Montepulciano is a convenient spot as you can reach the Val d’Orcia, Montalcino, etc, from there. Siena is another fantastic option, but it’s definitely a small city, not a tiny town.

Saturnia is pretty far out of the way from everything else on your list, so unless it’s your dream destination in Florence, I’d consider trimming that. 🙂

Hi, Your article is very informative. Thanks. One question, I understand that leaving anything in the car in Italy is not a good idea as it can be stolen. What about these small towns in Tuscany? Is it risky to leave luggage in the trunk when parking there, too? Thanks

That’s essentially down to your personal risk tolerance. Many people leave luggage in the car when they have no other good option if it is kept out of sight in a locked trunk.

Obviously, there’s always a small risk with that, but it’s a fairly common practice.

The most important thing is to make sure nothing visible is left behind.

Thank you for such a insightful article, it has definitely helped to make a road trip through Tuscany feel less daunting!

Are there are places on your list that are more or less English friendly? We will obviously try to learn what we can in Italian, but it is always helpful to know 🙂

My husband and I previously visited Florence and did a day trip to Pisa, Siena, and San Gimignano. The scenery was so breathtaking it quickly made a road trip through Tuscany a MUST on our bucket list! Having already visited those places (wouldn’t mind visiting San Gimignano again!), what would be your top picks for 5-6 nights (not including Florence but starting from there)? I would love to make a stop at Saturnia if time allowed. Thank you SO much for your suggestions!

Hi Samantha,

Thank you so much! Glad we can help. 🙂

Unless you go exceptionally off the beaten path, you won’t have any problem using English (plus body language/hand signs/etc) in Tuscany, so don’t worry! Definitely learn what Italian you can, but Tuscans are very friendly and exceptionally used to foreigners.

Since you guys have already done quite a bit in the northern part of Tuscany, I recommend heading to the southern part! Montepulciano, the Val d’Orcia (including towns like Pienza and Montalcino), Cortona, and Saturnia, make a great loop.

You might also look at taking a day trip to Civita di Bagnoregio, Orvieto, Perugia, or Assisi. Those places aren’t in Tuscany but are wonderful, and depending on your itinerary might make fun additions.

This is so helpful Kate, THANK YOU!!!! This will be my first time in Italy, I’m traveling solo, and I’ve never driven outside of the U.S. before, so I’m thinking I’ll stick to trains to get around this time (which I know will limit how much flexibility I have). Are any of these towns easily accessible by train from Florence (and/or each other)?

Happy to help, Tara!

Yes, Lucca, Pisa, Arezzo, and Siena are all easy to get to by train.

The smaller hilltop towns are generally harder to access without a car, and many don’t have train stations. You can technically get to Montepulciano by train, but the station is outside of town and you’ll need to catch a bus or taxi to get all the way there.

If you want to visit a few of the tiny hilltop towns, I’d recommend signing up for a day trip one day–we link a some popular ones in this post: https://www.ourescapeclause.com/best-day-trips-from-florence-italy/

Generally from Florence, you can find either day trips that focus on the north (San Gimignano is a common stop) or the southern Val d’Orcia towns. They’re a great way to see harder-to-access spots while letting someone else deal with the driving and parking!

Thanks so much for responding and for the additional tips! <3

Hi Kate! Thank you, thank you, thank you for the wealth of information. Very helpful for our upcoming visit!

Any possibility of emailing you directly with a few more questions?

Thanks, Lori and Steve, USA, coming in October for our 60th birthday’s!!!!

Yes, of course!

We’re not travel agents and don’t plan/book trips for people, but we’re always happy to answer a few questions and point travelers in the right direction. 🙂

Happy early birthdays!

Hello again, We will only have about 4 (3 full) days and nights to explore Florence and Tuscany. We hear that Florence is not terribly large and is very walkable? Would it be practical and safe to utilize motor scooters to do so? The countryside is a PRIORITY, but we are considering not venturing too far from the city to limit travel time. We’d like to spend at least one night in the city, and at least one in the country. And we very much want to explore a couple of very small villages. Suggestions?

Would you recommend purchasing train tickets in advance, or is it really not necessary? Likewise for renting a car, and making hotel reservations (First week of October).

For the train tickets–it depends. For high-speed trains across long distances, like from Florence to Venice, yes, absolutely book in advance. The prices increase dramatically as you get closer to your dates.

For regional/slow trains, like taking a day trip from Florence to Lucca, there’s no need to book in advance.

What gets a bit confusing is that some lines, like between Rome and Florence, have both high-speed trains (essential if you’re making a day trip, as it takes under 2 hours), and regional/slow trains, which depending on the exact timetable can take anywhere from 3-5 hours or so.

If you want an overview of what’s available, we recommend using Omio to search for tickets and compare prices/timetables.

For hotels and a rental car, yes, you’ll want to book in advance. It’s not as urgent as in, say, July, but to get maximum availability it’s best to be prepared, especially if you have special requirements for your rental car such as wanting to rent an automatic.

I hope that helps and that you guys have a great time! October is our favorite month to be in Tuscany. 🙂

My daughter & I will have 5 days in Tuscany, have a rental car & want to visit mostly hill towns. Our hotel is outside Florence. We’d like to drive to Cortona then to for wine tasting, then to Monticchiello for a 7:30 dinner at Daria & spend night. Is this possible? Where do I find city maps?

I think you mean you plan to spend the night in Monticchiello? If so, yes, that will probably work well. Cortona is a bit out of the way as far as Tuscan hill towns go, but it’s very popular!

For city maps, your hotel will usually offer one, especially if you ask. For towns that you just take a day trip to, the easiest way to find them is to head to the tourism office (there’s virtually always a well-marked office in the town center).

Some tourism offices do charge a nominal fee for maps, so it’s a good idea to have a few Euros in small coins/bills on you when you go.

Totally loved it!!! Would you recommend doing this roadtrip with a child? I really want my 5year old daughter to witness new cultures and enjoy some holidays with mum and dad!

Of course it depends on the child, etc, but it’s definitely possible! Italy is considered to be very kid-friendly, and kids are adored and welcome just about everywhere.

The distances in this road trip are also fairly short, so no extremely long car days to contend with.

I don’t see your 2 night Tuscany itinerary?

Hi Lorraine,

I’m not sure what you mean–maybe you’re looking for our 2 day Florence itinerary? Here it is: https://www.ourescapeclause.com/2-days-in-florence-itinerary/

I don’t have anything on spending 3 days/2 nights in Tuscany specifically, but for most visitors, I’d recommend spending 2 days in Florence and then taking a day trip to the countryside on the 3rd day.

Hope that answers your question!

Thank you very much for your article, it was very helpful to consider the cities/town to visit in La Toscana. What would you recommend me for a 10-day trip (honeymoon 🙂 ) by arriving to Rome? For sure, I want to rent a car and do all by car. Would it be better to take a train all over to Florence and from there do the trip all over to Rome? Is it a big deal if I do not have an international license? Thank you for your help.

You can definitely structure this trip as a road trip from Rome to Florence, touring Tuscany by road trip along the way instead if you prefer. For that version, you’ll likely want to start at Montepulciano and then make sort of a “V” shape ending in Florence. Keep in mind that you’ll probably have a one-way car rental fee if you do it this way.

In that case, you may want to add on a stop in Orvieto along the way as well–it’s in Umbria, and a beautiful place: https://www.ourescapeclause.com/things-to-do-in-orvieto-italy/

Having an international driving permit is required for non-EU drivers in Italy. It’s not often asked for, so you can choose to take the risk, but your rental company can refuse to rent to you and of course, you can have issues if you get into an accident, etc, if you don’t have one as well. They’re not complicated to get, so it’s much better to acquire one before going to Italy!

Hi! Thank you so much for this wonderful site – it is so informative!! We are planning 2-3 days traveling from Florence to Rome and wonder if there are private drivers for hire in Tuscany. Is that an option? And, if so, do you have a sense of how we would locate good drivers? Our concept is that it may be easier on us if we just left the driving to a trained professional local… your thoughts? Thanks again! Paul

We’ve never hired a private driver in Tuscany, so I can’t speak to that personally! I know that some private drivers and tours advertise through Get Your Guide. Other than that, I’d recommend asking your hotel concierge, they’ll no doubt know of someone.

However, if your goal is to travel between Rome and Florence, you could also easily take the train. If you’d rather take 2-3 days to do the journey and sightsee along the way, Orvieto and Siena are both stops to consider on the way.

If you’re confident drivers, though, that route is fairly simple–lots of highway driving, etc. If you’re considering the option of driving yourselves, I’d say there’s no real reason not to.

Hi Thank you for putting together all this info, it has filled me with excitement thinking about our trip this year. My husband and I are hoping to fulfil my dream of travelling to Tuscany this year at the start of April. We will be driving from the UK and stopping off in Normandy then driving across to Italy and Tuscany. The first large city we will enter is Turin before moving towards Tuscany. We have 7 days in Italy but we thought a circular road trip would be great made up of countryside, wine, food and wandering around towns and markets. I love the road trip based around Florence but given our route and our starting point, would you be able to recommend anywhere we should visit/stay/avoid that starts further north and drops into Tuscany. I don’t want to disappoint myself by making poor choices in destinations so any help would be much appreciated. Thank you

Sounds like a wonderful trip! We’ve driven from Portugal to Italy and/or France (and back) several times ourselves, so we’re very familiar with the breadth of the drive you’re taking on.

The Langhe region of Piedmont, located close-ish to Turin, is fantastic: think small towns, gorgeous views, delicious wine, and fewer crowds than Tuscany. You may want to consider a stop there before heading further south! We loved La Morra in particular, but there is lots to see around there, including Alba, Barolo, etc.

Depending on what route you take in, you may pass through Emilia-Romagna as well, one of our favorite foodie regions in Italy. There are a million places to fall in love with there, but Parma might be right along your drive: https://www.ourescapeclause.com/best-things-to-do-in-parma-italy/

Hope you guys have a fantastic trip!

Hi, I loved your article. My husband and I are planning to head to Tuscany in September. My thought is to arrive in Florence from the states and stay for 3 nights. Originally I was planning to head to Greve and stay at Borgo de Cabrea. for 5 nights and just do day trips from there. (The pictures of the hotel views blew me away). However after doing some more research, I’m thinking that I would leave Florence and head down to the Val d’ Orcia region for two nights, do some day trips from there, then head back up to the hotel in Greve for my remaining 3 nights. I don’t want to short change my experience in southern Tuscany. Looking for advice on where to stop on the way down, and the way up versus day trips from where we are staying. I’m thinking of stopping in Sienna on our way back up since it’s closer to Greve then we can avoid a day trip back down. Where do you think is good place to stop on the way down vs. places that would be better as day trips? Also any advise on where to stay in Val d’ Orcia region? Thanks for the advise on the cars. The site you suggested is much cheaper than the one I was originally looking at.

Those hotel views do look incredible!

With the caveat that you can’t make a very wrong decision in Tuscany, I’d recommend spending 3 nights in the Val d’Orcia area and 2 around Greve. Definitely check out the tiny town of Montefioralle when you’re in the Greve area, too: https://www.ourescapeclause.com/montefioralle-italy/

Siena is a decent-sized city rather than a hilltop town, so I’d spend more time there than you can–but if a couple of hours is all you can spare, visiting the Piazza del Campo + the Duomo + visiting one of the viewpoints to see the city from above will make for a memorable stop.

As for where to stay in the Val d’Orcia, we’re partial to Montepulciano as a base. It’s not in the Val d’Orcia, but nearby, well-connected, and beautiful. Pienza also makes an excellent base and has some hotels whose views I think you’ll also love: https://www.ourescapeclause.com/pienza-italy/

Depending on which route you take down from Florence, you may pass Monteriggioni, if so, that’d be a lovely stop during your drive.

Thank You so much for your response. After doing some of my own research and keeping your advise in mind, we booked a hotel in Montepulciano. I have another question for you. We are renting a car and tried discover cars. The prices for renting a compact car through Noleggiare are significantly cheaper than any other company. We need an automatic so it can get pricey. The reviews are mediocre and I was wondering if you had any experience with them. Thanks!

I don’t think we’ve ever used them in particular, but in general, we’ve never had any issues with a car rental in Italy and have zero brand loyalty with rental cars there. We tend to go with whoever is most affordable, as the prices can vary so much. We do buy rental insurance, though–for us, it’s worth the peace of mind.

Hi Planning on driving from Rome to Florence, taking our time. Where would you rent the car? And can you drop off a car in Florence if you rent in Rome. Thanks

Hi Sebastiano,

Personally, we’d rent the car in Rome wherever we could find the best deal–we’re not particularly loyal to any one car rental company.

You can definitely rent a car in Rome and drop it off in Florence, however, you’ll likely incur a one-way rental fee. These can vary dramatically, but are usually pretty reasonable if you’re picking up and dropping off the car in the same country (driving from Italy to Switzerland, for example, would be a different story).

Hi! I liked your insights very much, I hope to go visit Tuscany soon with my family. Though you didn’t really mention seaside areas – I guess it’s because people don’t tend to visit Tuscany region because of beaches, but still, there IS some seaside (judging from map sorry), and I would like to know more, either if you had any experience, or from locals or friends. I clinged to the one photo of a beach at Livorno. I was wondering, if it is worth seeing the seaside as well, if there are any beaches, maybe areas where swimming is not recommended, dangerous tides, sharks… or are there nice places as well, worth visiting. Is the shore easily accessible? The shoreline area is more flat I guess, less hills there as I assume again, from maps…

You’re right, I didn’t include seaside areas because typically, that’s not what non-Italian travelers are looking for from the Tuscany region. You’re right that it has a lovely coastline, though!

A few popular beach towns in Tuscany include Viareggio and Forte dei Marmi. Livorno is a popular cruise ship stop, and has a historic fort right on the water. Don’t miss the view from Terrazza Mascagni if you go!

If you want to go further off the beaten path, the Tuscan island of Elba (where Napoleon was once banished to) is beautiful.

If you’re in a beach town, you’ll definitely have access to the sea!

Will be in Tuscany for four days and thinking one day each in Pisa, Florence and Montepulciano (or combine a couple (like Pisa/Florence). Can you suggest a good home base area? We will have a car – any suggestions for a couple of one day road trips (if we can combine P, F or M) to visit wineries, different towns, etc? So many things to see it’s hard to decide and are hoping you can help us out. Thank you so much!!!

Hi Collette,

If you plan to have a car, I’d recommend staying outside a city center and enjoying the countryside a bit. That’s the advantage of having a car in Tuscany!

I’d also recommend combining Lucca with Pisa–Pisa doesn’t take long to see, but Florence definitely takes a full day at a minimum assuming you want to go inside a museum, up a viewpoint, etc.

On the route from Florence to Montepulciano, Monteriggioni and Siena are great options (depending on which route you take). The Chianti area is also between the two, though it’s a bit more out of the way to access!

San Gimignano and/or Volterra would also make a great day, and would be enhanced by having a car.

Deciding where to stay can be fairly flexible, as all of those places can be visited as a day-trip from the others, but I’d choose based on your priorities, as you’ll have some long drives round-trip. The Siena area makes a great base if your priority is Montepulciano and towns like the Val d’Orcia. The Lucca area or Chianti area is lovely for accessing northern Tuscany (Florence, Pisa, San Gimignano, etc).

Ciao! Thank you so much for writing so much about Italy! It’s been very helpful while planning our upcoming Tuscany road trip. We’re planning to rent a car from Florence and are seeing a lot of negative reviews on all the cheaper Discover Cars rental companies. What rental companies have you used in the past and would you recommend them? Also, are there any we should stay away from? Trying to be budget friendly but also do not want hit with a bunch of fees after the fact. Thank you so much for your help!

Hi Natalie,

Happy to help!

Honestly, I could not even remember all the rental companies we’ve used in Italy, let alone in Europe. We’re not picky–we’ve used everything from big brands like Hertz and Sixt all the way to tiny local outfits that we spot on the ground. We’ve never been charged for damage, but we do take precautions.

Specifically, we ALWAYS thoroughly photograph and video (a full 360 video) the vehicle when picking it up, and we tend to buy the additional insurance as well. If you want to ensure there’s a 0% chance of being charged for anything, most companies offer a $0 deductible (in Europe, a deductible is called excess) policy. It’s an increase in the upfront budget, but offers a lot of peace of mind if it’s something you’re worried about!

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Tuscany Itinerary: See the Best Places in One Week (+Map & Tips)

By Author Jurga

Posted on Last updated: July 4, 2023

Planning a trip to Tuscany and not sure where to start and what’s the best Tuscany itinerary?

In our previous post, you could read about some of the most beautiful towns in Tuscany . In this article, you can read how to combine all those beautiful places (and some more) and create the perfect Tuscany trip itinerary that allows you to experience the very best of this picturesque region in one week.

How many days do you need in Tuscany

While you can see the main cities in 3-4 days, I recommend at least one week for Tuscany . This will allow you to see not just all the highlights of the best towns of Tuscany, but also to get a glimpse of the beautiful Tuscan countryside.

Below, you can find our suggested Tuscany itinerary that shows you where to go and what to see if you have one week in Tuscany. Read on!

How to see the best of Tuscany in one week

This Tuscany itinerary starts and ends in Florence. However, you can start and end in other towns and combine this trip with a visit to the other regions (e.g. Cinque Terre or Bologna ). This is really just meant to show you what’s possible and how to plan your time in Tuscany.

In order to see the very best of Tuscany and to experience some of its stunning landscapes, it’s best to visit the region by car. On the other hand, you don’t really need a car in the cities. Train connections between major towns in Italy are really good. So if you want to, you can visit some of the most beautiful towns using public transport only.

While this Tuscany itinerary is made assuming that you have a car, you can easily adapt it to your needs and your way of traveling. Just use this itinerary as a guide to the best places in Tuscany, how much time you need at each place, and how to best plan your trip.

At the bottom of the article, you can also find a map indicating all the places mentioned in this Tuscan itinerary. Read on!

One Week Tuscany Itinerary

Day 1 – florence.

Florence is one of the most beautiful cities in Italy and is not to be missed in any Tuscany itinerary.

One full day is the minimum that you need in order to see the main highlights of Florence . You can find more information, tips, and advice for visiting Florence in some of the more detailed guides to the city on our blog.

Not to be missed in Florence is the Cathedral (you can climb the dome of the Duomo as well), Ponte Vecchio, Accademia Gallery, Uffizi Gallery, and Palazzo Vecchio. If you have just one day in Florence, stroll the old town, check out the market, and walk to Piazzale Michelangelo for the best sunset view in Florence. Alternatively, have a drink at one of the best rooftop bars in Florence .

Stay in Florence for at least one night, in order to take full advantage of your time here. If you are traveling by train, I recommend a hotel close to the railway station. We recently stayed at Hotel Croce di Malta , an excellent mid-budget 4*hotel with a lovely rooftop terrace. If traveling by car, keep in mind that parking in the city is very expensive.

TIP: If you only have limited time and want to see the best of Florence in one day, be sure to book priority tickets for ALL the places you absolutely want to visit inside.

LEARN MORE: One Day in Florence

Day 2 – Florence to Siena

Leave Florence early in the morning and drive to Siena. Via Chiantigiana road SR 222 from Florence to Siena is very scenic, so you may want to take this road rather than a highway.

Spend the rest of the day exploring the beautiful town of Siena. Must-see in Siena is Piazza del Campo with its Palazzo Pubblico and the Mangia Tower, Siena Duomo (Cathedral), and the picturesque streets of the Old Town. 

TIP: Stay in Siena for 1 or 2 nights. Albergo Chiusarelli is one of the best picks in towns in terms of price/location/quality.

LEARN MORE: Best Things to Do in Siena

Day 3 – Val d’Orcia – Tuscan countryside

Here is a scenic road trip suggestion through the picture-perfect Tuscan countryside – Val d’Orcia – that you can take as a day trip from Siena.

If you have the time, you may want to spend a couple of days in this area, but one day is sufficient to drive through the scenic Tuscan countryside.

From Siena take the road SR2 to San Quirico d’Orcia. From here continue East along the SR146 in the direction of Montepulciano. This is the most scenic road in Tuscany – the one with the typical Tuscan landscapes you see in travel magazines and on postcards. 

Take your time to explore Val d’Orcia and visit at least a couple of charming little towns in the area: Pienza , Montepulciano , San Quirico d’Orcia , Monticchiello , Montalcino … Also the Abbey of Sant’Antimo is worth a visit.

With just one day in this region, I think I’d focus on Montepulciano, Pienza, and the countryside of Val d’Orcia.

TIP: If you are in Siena without a car, the best way to explore the Tuscan countryside is by taking an organized tour, e.g. this wine tour that brings you to Montalcino, Pienza, and Montepulciano from Siena .

READ ALSO: Best Things to Do in Montepulciano

Day 4 – San Gimignano and Volterra

San Gimignano and Volterra are both relatively small towns and their proximity to each other means that you can easily visit them in one day. 

San Gimignano , famous for its fourteen medieval towers has a tiny but very picturesque Old Town. It can get extremely busy during the day, so I recommend going there first thing in the morning.

One of the main places to see is Piazza della Cisterna. You can also climb to the top of the Torre Grossa.

Volterra has a great atmosphere in the evening, so it’s best to visit it later in the day. It’s a charming medieval town and it’s nice to just stroll the streets, check out some souvenir shops, and have a nice Tuscan dinner.

In my previous post, you can read more about what to see and do in San Gimignano and in Volterra .

TIP: One of the nicest and good price/quality hotels in Volterra is Hotel La Locanda . If you are on a tighter budget but want something really special, stay in Chiostro Delle Monache Hostel Volterra . It’s located in the 15th-century Franciscan monastery, has a great location, and free parking.

Day 5 – Pisa

Take your time to explore Pisa . Don’t limit your visit to the leaning tower of Pisa only! In fact, the leaning tower of Pisa is just one of the many monuments of Miracle’s Square. The Cathedral and the Baptistery are very impressive as well.

Pisa town center has no crowds and is very picturesque as well. Stroll the Arno River promenade and check out the Borgo Stretto, an old shopping arcade with many restaurants, cafés, and shops.

TIP: If you are touring around Tuscany by car, I’d advise not to stay in Pisa. Instead, drive to Lucca after you visited Pisa and stay there for two nights. Lucca has such a great atmosphere and several really nice hotels. They are located inside the city walls and so parking is not free (but possible). Check out  Hotel Palazzo Alexander or  Hotel Alla Corte degli Angeli .

Day 6 – Lucca

Lucca is our favorite town in Tuscany. You can see the main highlights in just one day, but you definitely won’t regret it if you choose to stay a bit longer. 

The main landmark is the city walls of Lucca which you can explore on foot or by bike. In fact, the best way to see Lucca is by taking a self-guided bike tour .

Piazza dell’Anfiteatro is another must-see in Lucca. Make sure also to climb at least one of the towers -Torre Guinigi or Torre Delle Ore for the best views in town. Here you can read more about what to see and do in Lucca .

TIP:  Take a food tour in Lucca – it’s a great way to explore the town and taste some of the typical local specialties.

Day 7 – Collodi, Pistoia, Prato, or the outskirts of Florence

There are several nice towns that you could visit between Lucca and Florence. Collodi, Pistoia, and Prato are all worth a detour.

We liked exploring the outskirts of Florence as well. You’re hardly out of the city, but the scenery is amazing. Take a road from Florence to Fiesole for stunning views and a beautiful Tuscan landscape.

Alternatively, you could easily visit Bologna. It’s located in the nearby Emilia Romagna region (so not in Tuscany), but is more than worth a visit if you find yourself in this part of Italy.

READ ALSO: Florence to Bologna Travel Info & Itinerary + Best Things to Do in Bologna

Where to stay for this Tuscany itinerary

Many people ask what’s the best area to stay in Tuscany . The answer really depends on what kind of trip you are planning.

If you are thinking of making a road trip in Tuscany , you can find my suggestions for hotels in each town in the day-to-day Tuscany itinerary above.

If, however, you don’t like changing hotels and packing your bags every day, you can also stay at one central location in the Tuscan countryside and take day trips from there. Sometimes you’ll need to drive an hour, sometimes two, so it’s not perfect, but it might still be easier and more relaxing, especially if you are traveling with kids.

TIP: If you want to stay in just one place for sightseeing, the best place to stay for exploring Tuscany would be the area close to Volterra or San Gimignano. It is very centrally located in Tuscany and is therefore ideal if you are looking to stay at just one hotel and explore the region by taking day trips. Here you can find the best deals for accommodation in Volterra and hotels in the San Gimignano area .

In fact, a few years ago we did just that when we were visiting Tuscany with our kids. We stayed at just one hotel in the Montaione area for 12 days and combined relaxing days by the pool with sightseeing. It worked well for us. You can read more in our best of Tuscany – itinerary from one central location post.

On our most recent trip to Tuscany, we were focusing on the area around Siena and Val d’Orcia, plus a few other places in Umbria too. For that, we opted to stay at this beautiful country house in Bettole.

There’s really not one ‘best’ spot to stay- Tuscany is way too big for that. So it all depends on which places you decide to visit.

Without a car: If you are not renting a car, the best places to stay for exploring Tuscany are either Florence or Siena. They both have good railway connections to the bigger towns and also a big choice of organized tours to the smaller villages in the countryside.

One week Tuscany trip itinerary map

Below, you can see an overview of this suggested Tuscany itinerary on the map.

Start in Florence, drive down to Siena, then on to San Gimignano and Volterra. Continue your trip towards Pisa and Lucca, and end in Florence.

Alternatively, continue to Cinque Terre, which is just a short ride from Pisa. Here you can find more information about how to see the best of Cinque Terre in one day .

Best Time to Visit Tuscany

Tuscany is a beautiful destination that has something to offer at any time of the year. That being said, the best time to visit Tuscany is in late spring or in early autumn. The very best months for sightseeing in Tuscany are May and September.

In the summer months, it’s very hot here. So if you are visiting in July or August, you may want to concentrate on the Tuscan countryside. A popular thing to do is rent a villa with a pool and make an occasional day trip to one of the smaller towns in the area.

Whereas the weather in late fall, in winter, and in early spring is more suitable for visiting the big cities rather than touring the countryside.

READ ALSO: Best Time to Visit Europe

So, this is our suggested Tuscany itinerary for up to one week. If you are planning a trip to Italy, make sure to check our Italy travel guide for more tips and travel advice for a big variety of popular destinations in Italy.

Alternatively, check our selection of articles below for more tips for a variety of destinations in Italy.

More tips for some of the most visited destinations in Italy:

• Best Things to Do in Rome
• Best Things to Do in Venice
• Best Things to Do in Milan
• Best Things to Do in Naples
• 2 days in Rome
• 1 day in Milan
• 1 day in Venice
• 1 day in Cinque Terre
• Tips for Visiting Rome
• Best Things to Do at Lake Como
• Bellagio, Lake Como
• Best of Lake Garda
• Best of the Italian Dolomites
• Emilia Romagna Region
• Hiking in the Dolomites
• Tips for Visiting Cinque Terre
• Amalfi Coast Itinerary
• Italian Riviera
• Best Day Trips from Naples

READ ALSO: Best Places to Visit in Italy

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Monday 26th of February 2024

What a fantastic blog! This has really inspired me! I am thinking to visit Florence and Tuscany for a week in mid-June.

After 2 nights in Florence, and having a car, what town would you recommend to stay as a base and then do day trips? In terms of day trips, a must visit for us are Sienna, Lucca and Volterra. And definitely a winery but without driving to it. Advice very welcome!

Tuesday 27th of February 2024

Hi Teddy, if you want to visit Sienna, Lucca, and Voltera, you could stay somewhere in the middle between all these towns and make sure there's a winery nearby. I quickly checked something for you in the San Gimignano area which is very central and fits your criteria. There are several wineries that you can visit in that region and many accommodations, so you can find places to stay within walking distance to one or the other winery if you like. For example, this agriturismo (Capanna 1826) is just near this vineayrd. From what I read in the reviews of this accommodation, they even include a visit to their vineyard for free if you stay there. But there are many more options. You just have to do a bit more research and see what's available for your travel dates. If you don't mind taking a taxi to one or the other vineyard, then it will be easier. Just pick a hotel you like and then see what wineries there are nearby. Also, the San Gimignano area is just one of the many, so it's just a suggestion based on the info you gave. If you are traveling in June, I'd book your accommodations asap.

Ann Marie Pugliese

Friday 6th of October 2023

Hello, this blog seems very helpful. I am traveling to Italy for the first time with 9 family members for 2 weeks in June. We were trying to fit in so much, but don't think it's feasible with so many people. Was hoping to visit Venice, Tuscany, Rome and The Amalfi Coast. Also, we are planning to stay in Air bnb's along the way. Just not sure if we should travel to each area and stay for 3 days or find 2 central hubs and take day trips? Any insight you can offer would be greatly appreciated. Thanks!

Monday 9th of October 2023

@Jurga, THANK YOU SO MUCH!! Greatly appreciate the information!!

Sunday 8th of October 2023

Hi Ann Marie, since these areas are located quite far from each other and each has so much to offer, I think that staying in each place for a few nights is indeed better than looking for two base locations. You could start with 4-5 days in Sorrento (from where you can easily visit Amalfi Coast, Capri Island, Naples, Pompeii, etc.), then move on to Rome for 3-4 days. From there, take a train to Florence which is a good base for Tuscany, Cinque Terre, and also Bologna. Depending on what you want to see, you could stay here for 4-5 days. And finally, take a train to Venice and stay there for 2-3 nights. You can find lots of information for all these destinations on our blog. See an overview of all articles on our Italy travel page. This 2-week Italy itinerary might also be helpful - just to see what's possible and how you could structure your time at some places. For Amalfi Coast, take a look at this guide. Good luck with the planning!

Sunday 18th of June 2023

Hi, I am considering a 3 night stay in Florence next Summer followed by a week in self catering accomodation somewhere on the coast (we will not be driving, therefore, will be making use of public transport when we transfer from Florence to our second destination). We love Sorrento, Taormina and the Lake Garda towns and are wondering where on the coast (quite manageable by train from Florence), would have a similar vibe / buzz (i.e lively atmosphere) to these places? We would obviously fly into Florence but would be happy to go home from a different airport.

My other option is to follow on from Florence with a week in self catering accomodation (definitely with a pool to cool off), within walking distance of one of the cities / towns in the region - but I'm having difficulty deciding between Siena. Lucca and San Gimignano (or somewhere else with a Sorrento type 'feel' to it!!).

Any suggestions / advice would be gratefully received

Many thanks, Becs

Tuesday 20th of June 2023

Hi Becs, as you can imagine, there are too many options for me to give you any kind of reasonable suggestion. :) Also, there are two coasts - with places like Rimini or Ravenna to the east or the Cinque Terre area, Ligurian towns, etc. to the west. I assume you mean west? Without a car, by the sea, you could split your stay between the Cinque Terre area and Italian Riviera (e.g. Portovenere or Monterosso al Mare for a few days followed by a few days in Rapallo or St Margherita Ligure. If you are looking for a bigger city - check out Genoa. If you rather stay in central Tuscany, then Siena is definitely a lot better than San Gimignano - in terms of transport, things to do, etc. San Gimignano is a tiny village. Lucca is also very nice but not as centrally located as Florence or Siena for all the most popular places. Bologna is amazing too, btw! You can also just stay in Florence the whole time and make day trips. It also depends so much on what exactly you want to see. Good luck! Whatever you choose, you can't really go wrong - the whole area has so much to offer.

Kim Hendrickx

Monday 17th of April 2023

We are a family of 5 and we will be going on a week trip to Tuscany at the end of this month, We will be staying in a country guesthouse in Montaione. This will be our base to see different places in Tuscany, as we have a car. Could you recommend which cities are best to visit to get a real feel of Tuscany. We also want to do some wine tasting in Chianti and Montepulciano, so any tips on nice wineries to visit would be much appreciated. Thank you.

Hi Kim, you can find all the suggestions in this article and you may also want to take a look at this guide to some of the best towns in Tuscany. This is by no means a complete list and there are dozens of amazing places. But if this is your first time, you'll probably not want to miss the main cities such as Florence or Siena, so you need at least 2-3 days for that. The rest really depends on your interest and preferences. Of the smaller ones, San Gimignano is really nice, also Volterra, Montepulciano, and Pienza. If you have even more time, you may want to check out Montalcino and Cortona, also San Quirico d'Orcia. A week will fly by! As for the wineries, we really enjoyed a very unique wine cave visit in Montepulciano last summer. You can find more details in our Montepulciano guide. And this is a really nice winery that you can visit in Chianti. The problem with winery visits is that it's not really something you can do (and enjoy wine) if you have to drive afterward. So ideally, you have a dedicated driver, find a winery close to your accommodation and take a taxi, or book a tour (but those are usually only available departing from big towns so not ideal unless you stay in Florence or Siena). But definitely check out the wine cellar in Montepulciano if you go there! You can also taste just a bit of wine and buy some to take with you to enjoy at your accommodation. Enjoy your trip!

Tuesday 21st of March 2023

Looking for some advice on my trip to Italy in Aug/Sept. Flying into Venice and staying for 3 days then headed to Florence/Tuscany region for 5 nights. We don't want to rent a car but want to go wine tasting and check out the countryside and maybe the hill towns. After the 5 nights we head to Sorrento for 4 nights and finish off in Rome. Looking for advice on where I should stay in Florence/Tuscany area. Should I stay a few nights in both places or stay in one place and do day trips by train? Where do I take the train from to end up in Amalfi? Any advise appreciated.

Hi Rosemary, some of the best places to stay in Tuscany when traveling by train are Florence and Siena. You can find plenty of Tuscan countryside/wine tours from any of these towns (see here for tours from Florence and here - from Siena). If you don't mind changing hotels, you can spend a few nights at each of these; otherwise, I would recommend staying in Florence. There are many nice hotels close to the station (just in the center too), and it's very easy to explore the city or plan day trips. At the bottom of this guide of the best places to see in Florence, you can find some hotel recommendations for this area. For the Amalfi Coast, you'll have to take a train to Naples (there are high-speed trains from Florence to Naples - see here for train schedules and to prebook your tickets). Here you can find our guide on how to get to the Amalfi Coast from Naples. Have a great trip!

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tuscany TRAVEL GUIDE

Do picturesque Medieval towns, rolling green hills covered in vines, cypress lined roads, and some of the most delicious food in Italy sound like your idea of paradise? Then you need to visit Tuscany.

Home to the Renaissance capital, Florence, the region is renowned for its art history, Chianti wine, beautiful cities, and charming small towns that have inspired films like Under The Tuscan Sun and a whole suite of dreamy literature. Considered by many to be ‘quintessential Italy’, Tuscany is one of Italy’s biggest regions and it offers visitors many diverse experiences from city, to countryside as well as the seaside along the Mediterranean coast. 

Whether you’re dreaming about a trip to visit the Leaning Tower, sipping a glass or two at a Chianti winery, or eating the famous Florentine steak , travel in Tuscany is truly a dream come true for many. Keep reading to find out how to make the most of your time there with our Tuscany travel guide. 

Article contents

Where is Tuscany

Tuscany is nestled in the middle of Italy and on its western border are the Ligurian and Tyrrhenian seas. including an archipelago of 7 islands off the coast. The region borders Liguria, Emilia Romagna, Le Marche, Umbria and Lazio.

Florence is the capital of Tuscany and is easily reached from Rome in an hour and a half on the fast train; from Milan in two hours; and Venice in just over two hours. When visiting Tuscany by car, it is remarkably quick to enter into the countryside from Florence – the Chianti region is just 35km away. 

Map of Tuscany

Main cities and towns in tuscany.

Tuscany is the fifth largest region in Italy and is divided into different areas that each offer something new to discover from art and local traditions to wine, olive oil and the seaside. Some of our favorite Tuscan towns to visit include: 

• Florence: A trip to Tuscany is not complete without passing through Florence considered to be the birthplace of the Renaissance. Art and history lovers will delight as they stroll the streets once home to Leonardo da Vinci, Michelangelo, and Botticelli, and visit the Uffizi and Accademia Galleries as well as the Pitti Palace and Boboli Gardens. 
• Lucca : Encircled by Renaissance-era walls, Lucca is one of the most charming towns to visit in Tuscany (and beyond!) A trip to this gorgeous small city could include a bike ride along the walls, visiting the Piazza dell’Anfiteatro (built over an ancient Roman amphitheater), stunning villas like Villa Garzoni and Palazzo Pfanner, as well as Casa di Puccini – home to the great opera composer. 

Chianti / Siena Area

• Siena : Long time rival of Florence, this medieval city is stunning in her own rite. Siena is a place where traditions run deep, best embodied by the continuation of the Palio horse race that has been running since 1232! Explore the UNESCO Heritage listed old town, 12th century Cathedral, and of course the Piazza del Campo where the Palio is held every year. 
• Greve in Chianti : In t he heart of the Chianti wine region, Greve is a gorgeous town famed for wine, extra virgin olive oil, and the truffles that grow in the surrounding countryside. Wine shopping is on the cards here, as well as a delicious lunch in one of the town’s many excellent restaurants. 
• San Gimignano : Considered the ‘Medieval Manhattan’ thanks to its dozen towers still standing, San Gimignano is one of the most picturesque and atmospheric towns in Tuscany. Don’t miss climbing up one for a fabulous view! While you’re there, feast on their famous saffron, ham, with a glass of local wine – Vernaccia di San Gimignano.

Val D’Orcia

• Pienza : Cheese lovers will want to visit Pienza to try their incredible Pecorino sheep’s milk cheese! Redesigned by Pope Pius II to be a ‘utopia’, the town is full of charming cobblestoned lanes, romantic street names, and the scent of fresh cheese wafting through the air at every turn. Enjoy breathtaking views of the Val D’Orcia countryside from the Piccolomini Palace gardens.
• Montepulciano : In the heart of Tuscany’s southern wine country, Montepulciano is said to be o ne of the most beautiful Tuscan Medieval hilltop towns. Indulge in wine tasting of the Vino Nobile di Montepulciano and feasting of cheese, pork, thick hand-rolled pasta, honey, and lentils here. 
• Montalcino : To enjoy some of the most stunning views over the Arbia, Asso, and Ombrone valleys, you can’t miss a stop in Montalcino. Covered with olive orchards and vineyards, Montalcino is known for its Brunello di Montalcino wine so plenty of tasting is recommended here.

READ: Our full guide to visiting the glorious Val d’Orcia .

Arezzo Province

• Arezzo : The setting for Academy Award winning film La Vita e’ Bella (Life is Beautiful), Arezzo is a total gem. Settled by Etruscans, it is full of fascinating history and architecture that also spans across Roman, Medieval, Renaissance, and Romanesque periods. Visit to enjoy quiet piazzas, long lazy lunches and the monthly antiques fair.
• Cortona : Made forever famous thanks to Frances Mayes’ Under the Tuscan Sun , Cortona is a sweet Medieval town with Etruscan roots and incredible hillside views across the Valdichiana valley and Lake Trasimeno. Wander its narrow streets, admire the Medieval architecture, and pay a visit to the Museo dell’Accademia Etrusca to learn more about its past.

Province of Pisa

• Pisa : Made forever famous thanks to the Leaning Tower , you can’t miss the main attraction of this city. However, you should linger a little longer in Pisa. A trip to this university city will uncover beautiful historic churches, Medieval castles, and ancient bridges across the River Arno. Strolling through the beautiful old town pre or post ‘tower-selfie’ is something many visitors miss out on in their rush to see the main attraction.
• Volterra : We think it’s impossible to visit too many pretty hilltop towns, and Volterra is a highlight. A walled town perched atop a mountain, Volterra has a long and fascinating history that dates back to before 8BC. Explore along the ancient walls and fortresses and go shopping at one of the many artisan shops in town.  

Tuscan Coast

• Grosseto : The capital of Tuscany’s ‘ Maremma ’ coast, Grosetto is an interesting town rebuilt by the Medici family in the 16th century. Visit the Archeological Museum, Dante Alighieri square, and Cathedral of San Lorenzo. 
• Porto Ercole : Don’t miss this  pretty seaside town in the Maremma along the Monte Argentario peninsula. Enjoy swimming and boat trips, exploring Spanish forts and indulging in the delicious seafood focused cuisine. 
• Capalbio : A charming town on the border of Tuscany and Lazio, Capalbio is also known as the city of artists. Don’t miss the Tarot Garden full of gigantic, grotesque statues created by Franco-American artist Niki de Saint Phalle.  It’s also particularly famous for its wild boar sagra (food festival) in September.
• Elba Island : Enjoy sparkling blue waters, and nature on this little piece of Tuscan paradise. Devoid of the crowds that flock to the more well known coastal areas of Italy, you can enjoy some tranquility and gorgeous beaches here. 

Top things to do in Tuscany

Whether you are a foodie, wine connoisseur, history buff, art lover, beach goer, or nature enthusiast, there is truly something for everyone in Tuscany. Here are some of the best things to do when traveling in Tuscany: 

Taste the celebrated local wines

Home to some of the best known wine in Italy, wine tasting is one of the best things to do in Tuscany. Visit the Chianti region to try the famous Chianti Classico wines made with Sangiovese grapes or head to the Val d’Orcia to try Brunello di Montalcino or Vino Nobile di Montepulciano.

Enjoy a stroll along the vines, and pay a visit to the cantina (cellar) to see how wine is made, before sampling the wine. Be sure to make an appointment to visit a winery in advance as you can generally not just turn up unannounced in Italy. An exception to this is Marchesi Antinori where you can drop in for a tasting at their futuristic wine room. Or, better yet, relax while everything is taken care of and consider joining this popular small group wine tour from Florence .

Explore Tuscany’s many Medieval towns

There are endless beautiful Medieval towns to visit in Tuscany so be sure to add some to your itinerary. Sweeping views over vineyards and olive groves are guaranteed, as is delightful meandering along cobblestoned paths, fantastic local food and popping into artisan workshops. If you’re not planning to drive, consider joining a day tour like this day trip from Florence to explore some of the top towns in Tuscany plus have lunch at a winery.

Relax at a thermal spa

Did you know Tuscany is famous for its healing thermal spas? The most famous to visit is Saturnia where thermal warm water cascades down the slope of a hill into gorgeous pools of 37°C water for you to bathe in. Besides the free baths, you can also visit many luxury thermal spa hotels in and close to the Val d’Orcia area like the Terme di Saturnia Resort .

Explore the best art galleries in Florence

If you’re a lover of art, then you really cannot miss a trip to Florence. Start with the world renowned Uffizi Gallery, home to Botticelli’s “Birth of Venus”, statues by Michelangelo and more. Next, you’ll want to visit the Galleria dell’Accademia where you’ll find Michelangelo’s original and magnificent statue of David. Get the most out of your trip with a guided tour with Liv Tours .

Go truffle hunting

Try your luck finding the elusive white or black truffle when in Tuscany! The best area in Tuscany for truffle hunting is near the town of San Miniato. Try this tour that includes a delicious truffle laden lunch after your hunt in the area.  In fact, the town hosts a spectacular truffle sagra (festival) every weekend in November which is well worth the trip. 

Bike around Lucca’s Renaissance city walls

Lucca is a jewel of the region and easily reached from Florence by car or train. Do as the locals do whilst there and hire a bike for the day to ride around the city walls and take in the gorgeous views with the wind in your hair. Try this bike tour that includes some stops to sample typical cuisine too!

What to eat and drink in Tuscany

Tuscany is home to many delicious specialties, but some favorites you can’t miss include: 

• Bistecca alla Fiorentina: Perhaps the most famous food in Tuscany is Florentine steak. This cut of beef comes only from the white Chianina cows found in Val di Chiana, is served on the bone and is dry aged for between 15 to 20 days. Florentine steak must be served rare for the ultimate mouth watering experience.
• Lampredotto : Florence’s favorite street food is a panino filled with the fourth stomach of a cow and a zesty salsa verde
• Cinghiale pasta : wild boar pasta served with long pappardelle noodles.
• Ribollita : a hearty Tuscan bread and vegetable soup, including locally grown cavolo nero (black kale)
• Finocchiona Salami: Tuscany is known for its spectacular cured meats, but perhaps the best is the finocchiona – a pork salami flavored with fennel.  
• Schiacciata di Uva: Look out for this treat during the harvest season (Sept-October). It’s a fluffy bread made with focaccia dough and small, sweet, black grapes called uva fragola . 
• Castagnaccio : A Fall/Autumn favorite, this chestnut flour cake is made with new olive oil, raisins, and pine nuts and is both gluten-free and vegan friendly.
• Extra Virgin Olive Oil: Peppery Tuscan EVOO is revered throughout Italy. If you are lucky enough to travel to Tuscany in Fall/Autumn, look out for ‘olio nuovo’ or new oil that has just been pressed for the best olive oil tasting of your life.
• Chianti Classico: Tuscany is known for many wines, however Chianti Classico is the most quintessential. Don’t miss tasting some on your trip. 

Where to stay in Tuscany

There are many different accommodation options available in the region including hotels, apartments, B&Bs, and agriturismi (farmhouses). Tuscany is no stranger to tourism, which means that there are well-established facilities built up in the region to suit a range of group sizes, budgets, and accommodation needs. 

Florence makes for a great base to explore Renaissance art as well as day trips into the Chianti countryside. Whether you’re driving, going with a tour group, or taking public transport, you can also easily visit Siena, the Val d’Orcia, Pisa, Lucca, and Arezzo for the day from here.

We like the St Regis Hote l for 5 star luxury or try a more budget friendly option that’s extremely well located like Hotel Perseo . Take a read of our article on where to stay in Florence for more ideas.

If you’d like to immerse yourself in the countryside for a few days, then consider staying in the Chianti or Val d’Orcia areas. Castellina in Chianti, Pienza, and Montepulciano all make wonderful bases for exploring wineries, and hilltop towns. Consider staying at a winery like Querceto di Castellina or an agriturismo like Merigge Montepulciano for a more immersive experience. 

Lucca is another excellent base to escape the crowds with easy access on the train to Florence. From here, you can explore the Garfagnana area too with a car. Find our recommendations in our guide on Where to stay in Lucca .

Siena is perfectly placed for visiting the southern part of Tuscany, the Val d’Orcia, if you prefer to have city accommodation and are prepared to drive as this area is not well serviced by efficient public transportation.

For those looking to soak in what life in a real Tuscan town is like, consider basing yourself in beautiful Arezzo instead. It’s well connected by train and lacks the crowds of Florence and Siena. 

When to go to Tuscany

Spring is a wonderful time to visit Tuscany as the countryside turns green and temperatures are pleasant for exploring (46-66°F or 8-19°C). Enjoy new season artichokes, fresh fava beans, fresh cheese and plenty of food festivals like the cherry sagra or the frog festival.

Summer in Tuscany can get very hot with temperatures easily reaching 86F(30C) and beyond. Florence gets particularly hot and humid during this time, so staying outside the city and having access to a swimming pool or the beach is a good idea. 

Fall/Autumn is a wonderful time to visit as the region comes to life with the harvest season . If you’re a foodie, you’ll enjoy truffles, porcini mushrooms, saffron, new wine and extra virgin olive oil as well as a suite of sagre or food festivals. Look out for the sagre (food festivals) in Panzano and Greve where the towns are decorated with flags and colorful decorations, as well as the Pecorino di Pienza festival dedicated to the delicious sheep cheese. 

The wintertime in the region can get very cold and even snow with temperatures around 38-42°F (3.5°C – 5.5°C). During the festive season, there are wonderful Christmas markets held all over the region particularly in Florence, Sien a, and Arezzo. Prices are a little cheaper and crowds a little thinner too after the new year. 

How to get to Tuscany

It might surprise you to learn that the main airport in Tuscany is Pisa and not Florence. Florence is a very small airport that doesn’t have great connections so consider flying into Pisa instead from abroad or other major Italian cities. 

Traveling by train to Tuscany is easy from the major Italian cities. Take the high speed rail services and you can be in Florence in 90 minutes from Rome, 2.5 hours from Venice, under 2 hours from Milan and around 40 minutes from Bologna.

If you’re driving, you can reach Florence from Rome along the A1/E35. The average travel time ranges between 2 hours and 30 minutes and 3 hours and 15 minutes depending on traffic. From Milan, you’ll travel south along the A1 with travel time around 4 hours. From Venice, the trip is a little shorter around 3 hours along the A13.

How to get around Tuscany

Florence is best explored by foot and a car will only frustrate so it’s best to leave this parked during your stay in the Renaissance city.

There are reliable and fast regional train routes to Lucca, Arezzo, and Pisa. Florence to Lucca takes around 1 hour and 40 minutes, whilst Pisa and Arezzo are quicker and take less than an hour by train. Getting to Siena however takes about two hours so is much slower via train. Book your train tickets in advance online with Omio . 

It’s best to hire a car to explore the countryside including the Chianti, Val d’Orcia, and Maremma regions. We recommend renting your car with Autoeurope or Car Rental by booking.com from the airport (Pisa or Florence) to avoid navigating through sometimes stressful driving in the city centers. Read our driving tips for Italy for more information.

For those not wanting to drive, consider hiring a private driver or joining a tour to experience the best of the countryside. 

Let’s go to Tuscany!

Are you inspired to visit after reading our travel guide to Tuscany? If you would like to learn more about this gorgeous region of Italy, have a listen to our podcast episode about the Chianti region , or exploring Florence .

We have a wealth of further information available on our site to read including articles on best agriturismi in Tuscany , hidden gems in Florence , best museums in Florence , and Florence highlights . 

Want to discover Tuscany with us? For a deeper local connection, why not join one of our Tuscany small group tours . 

Road Trip in Tuscany: Itinerary & Our Tips for the Most Beautiful Destinations

Ciao Toscana! Hello beautiful Tuscany! It’s no secret that we fell in love with this region instantly, it was love at first sight . Tuscany has this unique combination of Italian lifestyle and holiday flair. Our road trip through Tuscany was one of our best trips and most memorable trips (not just because we got to spend it with family).

In this travel guide, we share with you our itinerary and which places we visited on our Tuscan road trip. As always, we have included our personal tips as well. All the destinations on our road trip can be found at the end of the article on an interactive map.

• 1. Tuscany Road Trip: What is Tuscany like? 

2. Itinerary through Tuscany: The Stops of our Road Trip

3. map: overview of our road trip through tuscany, 4. extra travel tips for your tuscany road trip, 1. tuscany road trip: what is tuscany like  .

Olive groves and vineyards as far as the eye can see, rolling hills and picturesque towns: Tuscany is home to some places that are too beautiful to be true, with incredible photo opportunities all around.

In the heart of Tuscany, you’ll find beautiful, romantic cities , such as Florence with its stunning cathedral. But the smaller cities are the ones that really captivated us. We were particularly taken by the small charming town of Lucca, with its well-preserved medieval city wall.

However, Tuscany would not be Tuscany without its characteristic landscapes: the gentle, rolling hills are mesmerising in the golden hours – as are the lovely cypress trees and olive groves.

Mornings are best spent with breakfast from local places, and the evenings are best spent enjoying sunset out in the countryside – you can’t get more Tuscan than that! You’ll find it easier to switch-off and be more in the present – life slows down here, just enough that it’s therapeutic.  

Florence is the ideal starting point for a road trip through Tuscany because being the capital of Tuscany, it is home to one of the largest airports in the region.

With almost 400,000 inhabitants, Florence is not a huge city, but certainly larger than expected. It’s also very touristy with large crowds, especially in the centre. Nowhere else in Tuscany was coffee more expensive than in Florence.

The most famous sight in Florence is the Uffizi Gallery – a complex of buildings that has now become one of the most famous art museums in the world. Therefore, it might be a good idea to get your tickets in advance. One of the highlights was the stunning cathedral of Florence called Santa Maria del Fiore . We were speechless at the sight of it, this is one of the most beautiful cathedrals we have ever seen.

Our tip: enjoy a magical sunset overlooking Florence from the Piazzale di Michelangelo . This is far from a secret, but the view from up here is simply incredible.

Our hotel tip for Florence: Corte Calzaiuoli Elegant Suites Beautiful, very stylish, small boutique hotel right in the centre of florence. Great location, very good breakfast – one of the best accommodation on our road trip.

Of all the destinations we visited on our road trip in Tuscany, we found Lucca particularly charming and would highly recommend you to see this place for yourself. The architecture style has a very medieval feel and the city of Lucca is actually surrounded by an excellently preserved medieval city wall , which you can walk or bike around its entire 4 kilometre length.

One of the most famous sights in Lucca is Piazza dell’Anfiteatro . As the name implies, this square was built on the ruins of a Roman amphitheater, which is where it gets its characteristic oval shape from.

Our tip: do not miss the view from the Torre Guinigi (Guinigi Tower). From up here you have a beautiful panoramic view over Lucca.

Our detailed blog article: Lucca Travel Guide

Our hotel tip for Lucca: Il Pozzo di Santa Zita Very nice boutique hotel in a historic house with individually decorated rooms. It has a fantastic location in the centre of Lucca.

Welcome to the city that is home to the most famous attraction in Tuscany: the Leaning Tower of Pisa . The Leaning Tower of Pisa is one of Italy’s most well-known landmarks. No wonder the crowd was even bigger than we expected.

Of course it’s great to see the tower with your own eyes, but we have to admit that there are definitely more impressive and charming places than the grassy areas of Piazza dei Miracoli around the Leaning Tower of Pisa. During peak summer season, this place is swarmed by tour groups .

Right next to the Leaning Tower of Pisa is the Duomo of Pisa (Cathedral of Santa Maria Assunta).   Overall, we found the centre of Pisa less impressive than that of Lucca.

Our hotel tip for Pisa: B & B Di Camilla Lovely accommodation with a unique country house style. The location is central, but nice and quiet.

Upon arrival, we already had a good first impression of Volterra: The medieval city is perched on a hill and visible from a distance. Volterra’s twisting labyrinth of narrow streets had the potential to be one of our favourite places in Tuscany, if it wasn’t so crowded.

Nevertheless, Volterra is definitely worth a stop. Fun fact: Volterra is also called the alabaster city , as it was well known for its mining and processing of alabaster. That’s why you’ll find countless shops selling alabaster products in the city centre – most of them are your typical souvenir shops.

Our accommodation tip: Villa Loghino Very stylish accommodation in an old country house with a pool. It’s located outside the centre of Volterra and it’s very nice and quiet.

San Gimignano

The next city on our Tuscany road trip is San Gimignano. San Gimignano is one of the most impressive cities in Tuscany and also known as the “Medieval Manhattan” . If you approach San Gimignano, then you immediately see why: 15 medieval towers reach up towards the sky, giving the city its strikingly unique appearance.

One of the highlights is the view over San Gimignano from the towers. Perhaps the most famous one is the lookout point from Torre Grosso . Although most of the information you see on the Internet says that this is the only accessible tower, we actually found ourselves on another tower. However, in our particular case, this alternative tower was actually home to an apartment. Therefore, mostly likely only accessible if the apartment is not currently rented out. Either way: San Gimignano from above is a must-see.

Our tip: There is a lovely winery near San Gimignano called Teruzzi & Puthod , where we stopped to look around. If you want to buy a bottle of wine or two, then this is the place for you. One of the classics from this particular winery is the Tuscan white wine – Vernaccia di San Gimignano.

Our detailed blog article: San Gimignano Travel Guide

Our hotel tip for San Gimignano: Podere Sant’Elena Very nice accommodation in a restored country house with pool and large garden. Just outside San Gimignano, but very idyllic.

For two things, the small, charming place is particularly well-known: Firstly, you will find plenty of wineries in and around Bolgheri. And on the other hand, the journey to Bolgheri is very special: you drive through the famous cypress avenue , the so-called Viale dei Cipressi. Centuries-old cypress trees line this street.

Bolgheri itself is a charming little town that is explored fairly quickly. Worth seeing is the castle of Bolgheri , through whose gate you also drive when you come to Bolgheri. Otherwise, you can pass the time in one of the wine bars – there are some in Bolgheri.

Another must on a Tuscany road trip: Siena. Siena, located in the heart of Tuscany, is considered one of the most beautiful and charming cities in Italy . Not for nothing is the old town Siena UNESCO World Heritage Site.

The best way to start your city tour is in the most important square of Siena, Piazza del Campo . This sprawling, shell-shaped space is a popular meeting place for locals and tourists at any time of the day.

From the tower of the Palazzo Pubblico , the Torre del Mangia, you have a magnificent view over Siena. More than 400 steps have to be overcome before you can enjoy the panoramic view over Siena. He is really breathtaking!

Our detailed blog article: Siena Travel Guide

Hotel tip for Siena: Casatorre dei Leoni Beautiful and very tasteful accommodation in a historic house right in the center.

Val d’Orcia

One of the most iconic destinations on our Tuscany road trip is the beautiful Val d’Orcia, located south of Siena. Here all the Tuscany clichés that you have in your head become reality.

You can look forward to beautiful, medieval towns surrounded by a picturesque, gently rolling landscape. We particularly liked Pienza, Montalcino and Montepulciano.

For wine lovers, the Val d’Orcia is also a must on a road trip in Tuscany. The Val d’Orcia is home of the famous Brunello di Montalcino.

Our detailed blog article: Val d’Orcia Travel Guide

Hotel tip for the Val d’Orcia: Borgo Canalicchio Di Sopra Relais A wonderful hotel in a quiet location surrounded by vineyards and olive groves. This is how you imagine the perfect vacation in Tuscany!

To give you a better idea of ​​where all these locations are, we’ve mapped out all our Road Trip Destinations through Tuscany in this interactive map below.

Transport in Tuscany: Car Rental Tips

If you are not planning on travelling Tuscany with your own car, then we can highly recommend you book a rental car. In Tuscany, getting around by bus can be rather difficult, especially when it comes to smaller towns. If you have a car, then you can be much more flexible with your travels, which is a very important aspect for many people (like us).  

We always book our rental cars via Sunny Cars , who act as an intermediary. On their website, you’ll find an overview of the cheapest rental car offers from different companies such as Hertz or Europcar.

The biggest advantage of Sunny Cars is that you have full comprehensive insurance . So in the case of an accident, you will also be reimbursed the excess or deductible. The type of car is also important (eg. an SUV is perhaps a little unnecessary for Tuscany). We would say a mid-range car is a good ballpoint.  

You can search for cheap rental cars here: Sunny Cars

What is the best Season for a Road Trip through Tuscany?

Spring and autumn are most ideal for a road trip through Tuscany. The best months are perhaps May and June for Spring, as well as September and October for Autumn. The climate is usually pleasantly warm during these months and not too hot. Bonus: not so many tourists during these months as you would get in the peak summer months of July and August.

Tip: If possible, avoid the peak summer months (especially July and August). We have experienced what it’s like to travel Tuscany in August and can confirm that some places were just hopelessly overrun during this period. Especially places of historically significant sites, such as San Gimignano and Volterra. However, if you want to combine your Tuscan trip with a beach getaway on the coast, then perhaps you might prefer the warmer summer months.

How much Time should I plan for a Road Trip through Tuscany?

Difficult question as it really depends on the individual. We ourselves only spent one week in Tuscany, but at the same time, we could have easily filled in two weeks with beautiful destinations.

If you prefer a slower style of travelling, then we would recommend you allow two weeks , which will also give you enough time to explore a few places off the beaten path.

The distances between destinations should not be underestimated either because the Tuscany region is quite extensive : There are actually nine provinces, which theoretically would take several hours to cover them all. Although Tuscany does not seem as big on the map, you should also keep in mind that some of the roads are not perfect. You might find yourself driving on the country roads, which often take longer than you might have originally planned for.

Day Trips from Base vs Staying in Multiple Places

You have two options here: either you have a fixed base with just one accommodation and do day trips from there. Or you hop around and stay in several places along the way. Both have their advantages and disadvantages.

1) Day Trips from Base: If you’re going with this option, then it makes sense to find a good base, preferably somewhere in the centre of Tuscany (such as Pisa or Siena), as this should help minimise the amount of travel time. The good thing is, you just need to pack what you need for the day. But you will end up spending more time on travel than the other option. We stayed in a historic estate in the province of Livorno and it was great being so close to the sea. Our tip: Before you book your accommodation, just check (via Google Maps) how long it will take to get to each of your planned destinations. That way, you can plan your day trips better and thus, make the most of your day.

2) Staying in Multiple Places: If you want to stay overnight in several places on your road trip, then you have the luxury of being a little more flexible. However, this also means you have to travel with all your luggage and you’re constantly having to pack and unpack your belongings. A good starting point would be Florence, where they have lots of international connections.

Disclaimer: Affiliate Links

This travel guide contains our personal recommendations in the form of affiliate links. If you book or buy something through these links, we will receive a small commission from the company. But this does not alter the price for you at all. A million thanks from the both of us!

Have you ever done a road trip through Tuscany? Perhaps you have extra tips? We look forward to reading your experiences!

You might also be interested in this

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Salento Travel Guide: Puglia’s Spectacular Peninsula

2 responses.

Thanks so much for all these amazing tips! I love how charming all the places look and now can’t wait for my trip to Tuscany this year 😍

you’re welcome! Have a wonderful trip to Tuscany. :)

Thank you for your message & safe travels, Kathi & Romeo

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The Tuscany Itinerary You Should Steal

By Helene Sula

It's clear why Tuscany has been the backdrop of many movies, books, plays, and novels. The cascading cobblestone streets, rolling green hills dotted with poppies, and the promise of delicious pasta and gelato make for the perfect escape. But there are so many cute little towns – how can you ever choose?! This guide is going to help you to see the best of Tuscany, the can't miss spots, and give you a full Tuscany Itinerary you'll want to steal. And you're welcome to do just that.

For the purpose of ease, I'm calling this post a one week Tuscany itinerary. But I also focused on cities outside of Tuscany, in the regions of Umbria – such as cities like Perugia and Assisi, Terni and Lazio. If that's confusing, just know that these regions of Italy are right next to each other so it made sense to go to all of them.

Below you can find a map of all the places discussed in this post:

In order to see the best of Tuscany you need a plan and most likely, a car. There are so many spots along the way you'll want to stop and gawk at or snap a photo of. There is public transportation, but to get to all the small, charming towns, a car is really best. This itinerary will be particularly helpful if you have a car. Luckily, renting a car in Europe is relatively inexpensive. I suggest checking rates with companies like Sixt where you can find great deals no matter where you're traveling.

The only problem with driving is finding parking. You MUST be careful where you park in Italy. You could wind up in a very interesting situation. I'll elaborate more down below!

I tend to be a go, go, go vacationer. But I had recently torn my ACL while skiing in the alps and this trip to Tuscany was actually the perfect speed. It's nice to slow down the pace and enjoy the countryside and everything the region has to offer.

How much time to spend in Tuscany

You can easily stay under the Tuscan sun for months, years, even. But since we don't always have that much time I created a one week itinerary for Tuscany. I suggest 4-7 days in Tuscany to really see it all. Florence is a big city with lots of sights, so I suggest 1-3 days here alone. I've done trips that were 10 days in Italy and also spent 5 days just in Tuscany. This blog post is going to focus on other cities outside of Florence since you can read my guide for that city here .

How to get to Tuscany

If you're only spending time in Tuscany or want to fly directly, I suggest flying into Florence or Perugia. For this particular trip, I'd already been to Florence, so I wanted to focus on more of the countryside of Tuscany and the tiny villages that lie between the countless vineyards.

If you're coming from places like Rome or Venice, you can easily take the train directly to Montepulciano or Florence. I personally use GoEuro to book all of my train tickets in Europe. It's just the easiest, and it will give you a vast number of times, options, and prices.

Where to stay in Tuscany

For our home base, we chose Montepulciano. You know how when you lay eyes on somewhere new and immediately fall in love? That's how I felt at Sant'Antonio Country Resort in Montepulciano. Driving here was one of the most scenic roads I've had the pleasure to ride shotgun on. You'll see the typical Tuscan landscapes with rows and rows of vineyards and lush green hills.

We drove up from the train station in Perugia to one of the most picturesque scenes: miles of rolling hills, olive trees galore, and a 800-year-old former monastery turned hotel. We stayed in a large private villa that included a kitchen, large bedroom, bathroom, and my favorite part, a living room complete with a fireplace. Upon arrival, we cracked open a bottle of red wine and watched the fireplace flicker. It was the perfect start to our Tuscany trip.

Sant'Antonio was the perfect location to easily get from place to place, along with ample parking. The furniture is original seventeenth and eighteenth century and made for a cozy oasis in the hills. The rooms are stocked with local wines from the area along with water, beer, and soft drinks. There's even a swimming pool, a running path, and lovely garden.

The ambiance is peaceful and provides the perfect respite after a day of touring around Tuscany. I felt like I had my own moment of “Under the Tuscan Sun” in our lovely villa. We'd open up the windows and look out to see the gorgeous countryside. The owner is also one of the most dynamic people I've met and makes you feel right at home. I highly recommend Sant'Antonio .

Day 1 – 3 Florence

There is so much to see in Florence , so I suggest spending a good 2-3 days here. The architecture incredible, scenery captivating, and the museums are world renown. I suggest touring the Duomo , visiting the Uffizi and Galileo Museum , seeing Pitti Palace , and walking on the Ponte Vecchio .

If you have extra time, I suggest making a day trip to Pisa when you're in Florence. It's an easy half-day trip, and you can hop on a train to get there and see the leaning tower. You can read my guide to Florence and Pisa here . This post is going to focus on more of the Tuscan hillside towns and the scenic places you can see along the way.

Day 3 – Assisi and Perugia in Umbria

Technically, Assisi and Perugia are in Umbria, just after the border for Tuscany in Italy. We started the day by driving from Montepulciano to Assisi . The drive is about an hour and a half and is full of plenty beautiful sites along the way and bright reddish-orange poppies dotting the paved roads.

I was excited to see Assisi, as I grew up Catholic, I knew this was a hot spot for one of our most famous and important saints, St. Francis, and a UNESCO heritage site. The city is situated upon a hill and it rose out of the fog in the distance in front of us. We drove up to the city and found some free parking just before the pedestrian zone in the town.

As we walked into town I marveled at the beautiful stone of the homes and buildings. Fist, we went to Basilica of San Francesco d' Assisi . This is the burial place of St. Francis of Assisi and it's absolutely stunning inside. You'll find that St. Francis himself is buried in the church. Surprisingly, Assisi and the basilica have suffered a number of earthquakes. There has been extensive work to rebuild from the damage.

This well preserved city has a maze of cobblestone streets and you'll find a panini stand on nearly every corner. Eager to try some food, we picked up a toasted sandwich made with delicious cured meat and a glass of wine for an additional Euro. In all of the towns in this area each one has a myriad of flags, all different from town to town. We always stopped to take note of the city's new flag.

After getting a good view of Umbria from Rocca Maggiore , we headed on to our next destination: Perugia.

The drive from Assisi is heading back towards Tuscany and only about a half hour. I read online to park near the train station and take the Mini Metro up to the town. DO NOT DO THIS. There is plenty of parking in the old part of the town and I wish we had listened to our guts and not parked in the garage. I'll explain why shortly!

The Mini Metro is a hilariously small tram that takes you up to the hilltop and old part of Perugia. After taking the Mini Metro up, you take various escalators up to reach the top of the town. We walked around the town and stumbled into chocolate shops. Perugia is famous for its chocolate and Baci Perugina-  chocolate filled with hazelnut. You can go to the Perugina House of Chocolate to try all the different flavors and learn how it's made. My favorite was the delicious dark chocolate balls.

Since my sweet tooth wasn't satisfied yet, I opted for gelato at Gelateria Gambrinus . I'm telling y'all, this was one of my favorite gelatos I've had in Italy. And I've had a LOT of gelato.

We made our way to the main square, Piazza IV Novembre , with the gorgeous fountain, Fontana Maggiore . The medieval fountain dates back to 1275 and marks the end of the former Roman aqueducts for that area. Behind the fountain is the medieval cathedral, Cattedrale di San Lorenzo .

We walked over to the aqueduct after which is surprisingly uncrowded and offers one of the prettiest views in the area. Just a few minutes from this spot, we found a great place for dinner, Tozza e Bocconi . We were told a few places to check out and they all looked too touristy. Sometimes just wandering and finding a place is best.

A couple of bottles of wine later, we decided to go back. But on our way back to the metro, we stumbled upon a spot claiming, called Il Birrino, to be the “3rd smallest bar in the world.” I've come to find this is definitely false, upon various Google searches for, “smallest bar Perugia,” I've come up short.

Why you shouldn't park your car in a garage in Italy

Later than expected, we headed to the Mini Metro, only to find that it closes at 9 pm. Tired and weak (remember, I'm on crutches), we go to the bus stop. We called a cab as well, but they told us it would take 20 minutes which was the same time we'd have to wait for the bus. When we got down to the train station we walked to the garage. Curiously, no lights were on. And worse still, there was a metal grate locking in all the cars.

Puzzled, we walked around trying to find answers. We looked at all the signs posted at the entrance of the parking garage and nothing mentioned anything about closing times. We even asked police officers nearby and after they tried to help with no success, we looked online and found that the garage closed at 10 pm.

We were sleeping in Perugia that night.

Luckily, we found a really nice hotel that I'd actually recommend if you wanted to stay in Perugia or the Umbria region! Hotel La Rosetta was surprisingly nice and came with a great breakfast.

It was an unfortunate and somewhat hilarious situation. I've been told parking can be tricky in Italy, and now I won't be parking in a garage in Italy any time soon. Typically, if you want to park, the blue lines mean you need to “pay and display.” So, pay at the meter and display that you've paid with the receipt in the window. White lines typically mean free parking. As for garage parking, read the signs. If there are none, skip it.

Day 4 – Orvieto and Civita di Bagnoregio

After our hiccup the day before, we were ready to hit the road and explore more. We headed from Montepulciano to Orvieto , about an hour long drive. Orvieto is in the Province of Terni and holds one of the most incredible cathedrals, Cathedral of Orvieto . This small city dates back to 1290 and was once the center of Etruscan civilization. There's also the archaeological museum that features many artifacts from the Etruscan period.

This tiny town was easy to meander around and was pretty quiet compared to some of the other towns we visited. While the cathedral was impressive, I was most taken with the food. We ate at Trattoria Del Moro and before walking in, we talked to a guy outside who raved about his meal. “Best in Italy,” he gushed. He wasn't lying.

I had the most decadent four cheese ravioli. It was so simple but so divine. Michael ordered something called “nidi” which was pasta filled with pecorino cheese and drizzled with honey. If it sounds weird, it doesn't matter, because it tasted delightful.

After seeing the cathedral, it started raining, so we opted for gelato just beside the cathedral at Gelato at di Pasqualetti . Another good option in case it rains, or just in general, is the Posso dell Cava , an underground city. You'll find Etruscan homes and underground routes and tombs, textile workshops and more 36 meters deep!

Escaping the rain, we got in the car and went to Civita di Bagnoregio in the Lazio region. I had no preconceived notions about this place, but I can tell you it's worth it to see this incredible city. This beautiful hilltop top town is perched high above the valley, dramatically rising into the sky. The long bridge leads up to the city and is only wide enough for a moped or tiny vehicle.

The city truly looks like a painting and we stopped and stared before making the trek up. Again, this spot was relatively quiet. So much so, I was able to grab some pictures without anyone else in them!

Civita di Bagnoregio is known as the “dying city” as there isn't much life here and the erosion of the soft volcanic rock has put the place in danger. By the time we got there, the few restaurants there were already closed. There are a couple places to stay here, but it's mostly quiet. I highly recommend seeing this place as little has changed since it was built in the 6th century. The cobblestone streets and vine-covered villas are like walking into a fairy tale, complete with friendly cats who follow you as you make your way through the tiny village.

For dinner that night, we headed to the grocery store and picked up Italy's finest wines, cheeses, meats, and bread and went back to our sweet Sant'Antonio Resort in Montepulciano. I absolutely adore having a meal like this. It's cheaper and often very tasty. Another reason why I loved our stay in Montepulciano, was the ability to have a real dinner since we had a kitchen. We couldn't help having a fireplace and savoring the red wine from the region.

Day 5 – Pienza and Montalcino

Today, we focused on Tuscany with our first stop in Pienza , just twenty minutes from Montepulciano. This town was such a treat and felt like the perfect representation of true a Tuscan town. The gem of the city is a UNESCO world heritage site in the Val d'Orcia area of Tuscany. The Piazza Pio II is the main square which is flanked by the lovely cathedral, St Mary's , which is stunning inside. You'll also find great views behind the church.

We also found a wonderful gelato shop with a chef who came back to Italy to share his passion at Buongusto . He makes unique flavors based on the different seasons and the strawberry with rosemary flavor was surprisingly delicious.

Next, we headed to our much anticipated wine tasting and tour in Montalcino . We went to gorgeous Poggio Rubino for our wine tasting. For only $15 per person you get a tour of the winery (ours was even a private tour!) and you get to try various wines along with cheese, meat, bread, and olive oil and balsamic vinegar. This is one of the highlights of the trip for me. The Brunello red wine was exceptional and satisfying.

All of the wines, olive oils, and grappas are made with the highest quality ingredients. We even took some grappa to take home with us. Although, it didn't quite make it since we drank it all. I'd highly recommend this tour because it helps you have more of an appreciation for wine, it's a great price, and the wine was delicious.

To cap off the day, we went to hot springs of Bagni San Filippo . Tuscany has many hot springs which are thought to help cure and purify. The hot springs are free, and a different way to experience Tuscany. The water gets pretty hot, so no matter the season you can comfortably dip in.

Day 6 – Montepulciano and Siena

For our last day, we stuck around our home base and explored Montepulciano – a true Renaissance style town with a breathtaking view. The winding streets are car-free and allow you to meander from shop to shop. This city is known for the wine produced in the area, and they proudly offer a great selection.

We walked about the Piazza Grande , the main square of Montepulciano. It might look familiar, it's the scene from the Twilight saga, “New Moon.” We also peaked into the Chiesa di San Biagio , a beautiful Renaissance church. Then we opted for the phenomenal views while sipping cappuccinos and eating croissants.

If you have time, check out a wine bar with a terrace where you can watch the sunset. A good choice is E Lucevan Le Stelle .

From here, you can head an hour away to Siena for one of the most incredible churches: Cathedral Santa Maria Assunta . Also, climb up the Facciatone for panoramic views of the tower and the main square. You can also go shopping on Banchi di Sopra, the main shopping street.

Other towns of note in Tuscany are: Lucca, Chianti, Cortona, San Gimignano, and Volterra. If you'd like to round out your trip, you can do 7 days in Tuscany and hit up all these places!

If you have more time, head down to the Amalfi Coast (Capri, Positano, Amalfi, and Ravello) for an exquisite stay by the sea. See my full guide here .

In Tuscany, you can't go wrong. All of the towns are so lovely and each is a bit different and charming than the next. I'm sure the Tuscan hill towns will beckon you back again and again. Whether it's the delicious food, wine, or cypress-lined driveways, you'll find a reason to come back. Italy always seems to do that to us.

MEET THE AUTHOR

Helene Sula

I believe that one trip can change your life. It did for me. I'm a self proclaimed home body that quit her job, moved abroad, and more often than not, lives out of a carry-on bag. If I'm not traveling, I'm most likely re-reading Harry Potter or watching "Midnight in Paris" while snuggling my dogs. I'm a digital marketing expert who turned my love of travel into a full-time career. And I help others do it too.

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Tuscany Road Trip Guide: Tips for Visiting the Tuscan Countryside

Planning a road trip through Tuscany is no small task. There are so many tiny hillside towns, cypress-lined roads, fields of sunflowers, and gorgeous churches, how can you possibly see them all? It’s easy to get a perfect mental image of how the trip is going to turn out, but a different thing altogether to plan one that is going to work.

For starters, there is so much more research to do when you’re trying to find out which are the best towns in Tucsany. Each town has something special, plus there is less information online about lesser known towns – so you really have to dig for the inside scoop. Plus there are the additional logistics involved in driving a car in a foreign country!

That said, touring Tuscany by car is so worth it! Here are my top picks for places to visit the next time you’re in Italy, tips for a stress-free road trip, and my own Tuscany itinerary for 7 days!

“Life is a combination of magic and pasta.” — Federico Fellini Tweet this

Before you go to Tuscany

Renting a car – Whatever you do, MAKE SURE you get additional insurance for your car when driving in Italy. This applies to anywhere to drive in Italy whatsoever. Italians are known for bumping other cars in order to parallel park as tighly as possible, you don’t want to get dinged (ha!) for damage at the end of your trip.

We always rent our cars through DiscoverCars , and I definitely recommend them for finding the best price for your car rental.

What to pack – If you’re going to be staying outside of major cities, bring insect repellant if you’ll be traveling during the summer months. Besides that, sunscreen, hat, and sunglasses are no-brainers you’ll need to withstand the Italian sunshine. My favorite sunscreen of all time is this Biore SPF 50 sunscreen – it’s Japanese so you know it’s the absolute best.

Recommended Accommodation – Agriturismo La Dogana is a farm stay on Lake Trasimeno, complete with a swimming pool on a hill of olive trees overlooking the lake. Dreamy location and a great value, if you are looking for a home base to explore the area. Not only that, but when we went to a nearby restaurant, they gave us a bottle of wine to take home when they heard we were staying at La Dogana!

If you’re looking for a little relaxation, it doesn’t get better than this view at La Dogana.

Where to go in Tuscany on a road trip in 7 days

Here’s a high-level look at all these spots on the map! As you can see, everywhere is pretty close together, and driving from one city to the next doesn’t make more than two hours at most (that is, so long as the road isn’t under construction!)

• Day 1 : Florence
• Day 2 : Florence and Lago Trasimeno
• Day 3 : Assisi and Perugia
• Day 4 : Lago Trasimeno
• Day 5 : Montepulciano
• Day 6 : Siena
• Day 7 : Lucca

We stayed on the border to Umbria, so we visited places in both Tuscany and Umbria. That said, even if Umbria is less famous than Tuscany, it still has gorgeous towns which will be included in the list!

Best towns in Tuscany and Umbria

Here are all of the best towns we visited in Tuscany, Italy. At the end I’ll also list towns we did not visit, but are also worth checking out if you have the time or the drive (ha!) to see even more.

Montepulciano

Lago trasimeno, san gimignano.

Ponte Vecchio, the most famous bridge in Florence, Italy

First stop on the roadtrip was Florence – no trip to Tuscany would be complete without it, and after going, I understand why: Florence is beautiful, colorful, and delicious. Florence is especially known for Bistecca alla Florentina , the local way to prepare a T-Bone steak. In short, you get 1-1.5kg of meat, cooked rare, and served up all for you. If you’re not carnivorous, Florence is also famous for gelato within Italy .

Even though food is probably the number one thing on my mind when going to any new city ( especially an Italian city), Florence has some of the most recognizable art of all time, such as the statue of David and the Birth of Venus. I’d argue that the city itself is just as much a piece of art with people living in it. Do not miss Florence on your Italian roadtrip!

Photo taken from the Tower of Palazzo Vecchio

Things to do in Florence

• Il Duomo – The Florence Cathedral is easily the most famous sight the whole city! There can be a MASSIVE queue to enter the cathedral, so be prepared for that (but at least it’s free). Don’t miss climbing to the top of the Duomo for incredible views over Florence. Ladies, be sure to have a way to cover knees/ankles because traditional Italian churches don’t allow you to waltz in with a ton of skin showing. I used a jacket to make it work.
• Uffuzi Gallery – Probably the most famous art museum in Florence, this gallery is home to Botticelli’s “Birth of Venus”, Carvaggio’s “Medusa”, plus works by Da Vinci and Michelangelo among many others. One of Europe’s oldest museums!
• Accademia – This where you can see the famous statue of David by Michelangelo.
• Tower of Palazzo Vecchio – One of the best places for views of the Duomo and Ponte Vecchio! This tower has multiple levels you can use to take photos of the city and see famous locations from the air. Be aware, there a a whole lotta stairs to climb to get to the top but the view is worth it.
• Ponte Vecchio – Walk across this bridge, which has a bunch of shops on it. Come early in the morning if you want a little more space, it’s a pretty popular spot in Florence!
• Santa Croce – Probably the second most famous cathedral after the Duomo, there’s a big square in front of it where you can enjoy a coffee and people (or piegon) watch.
• Piazzale Michelangelo – Come here for one of the best views over Florence, which is completely free to access! Just cross one of Florence’s bridges to the other side of the river and start the climb. Be prepared, there are many stairs 😉
• San Lorenzo Leather Market – Florence is famous for its leather, but do watch out for shady deals .

Tower of Palazzo Vecchio , where you can get some of the best views over Florence

Where to eat in Florence

Cafe Zaza claims to have been the birthplace of Bistecca alla Florentina , the famous Florentine Steak that weighs a kilo and takes a small army to complete. Here you can order this famous dish, or a ton of other mouth-watering options. At the end, wash it all down with some tasty limoncello as the locals do.

Apparently Assisi is known amongst Italians, because everyone I told that we planned to go there gave me their congratulations. It’s easy to see why: this small town is one of the most impressive as you approach it from the road. High, white walls make it look like the city is meant to withstand siege, meanwhile the only thing threatening to breach its walls are fields of sunflowers.

This place has the highest concentration of real-life monks and nuns that I’ve ever seen – as well as tour groups. Luckily it only takes a little walking up the hill to escape them into Assisi’s charming stone alleys.

Basilica of San Francesco d’Assisi

Things to do in Assisi

• Basilica of San Francesco d’Assisi – St. Francis is buried in the lower cathedral, though both are beautiful. Again, like the other churches in Italy, you need to be prepared to cover your knees and shoulders.
• Rocca Maggiore – There’s also an old fortress above Assisi, climb up here for the best views over umbria’s rolling hills.
• Drink some wine – You can do this at just about any village in Tuscany, but there are some popular wineries here you can visit for a taste of local drink!

We went to Montepulciano with a single mission: wine. But on our way to the enoteca (wine bar), there were so many side streets that captured our attention that it took us almost an hour to get there, dispite how small Montepulciano actually is. Of everywhere we went in central Italy, this one had by far the most impressive views.

If you are looking for scenic drives through Tuscany , the ones leading to Montepulciano are just your ticket. You’ll pass fields of sunflowers, vineyards, country homes, cypress trees, and have plenty of fun winding roads to traverse on the way.

If you want to come to Montepulciano for wine-tasting, it’s important that you make a reservation if you want to combine the wine-tasting with lunch or dinner. If you just want to taste wine and perhaps nibble on small snacks, it’s usually possible to do that without a reservation. Italians tend to eat dinner around 8pm, so show up earlier to ensure you get a spot.

Things to do in Montepulciano

• La Bottega del Nobile – If you want to do wine-tasting in Montepulciano , check this place out. Here you can help yourself to a wide selection of local wines dispensed through a cool card system that keeps track of what you’ve tasted.
• Val d’Orcia – This ultra-famous valley is home some of the best views over the Tuscan countryside, and is wonderfully seen from Montepulciano.

While exploring Tuscany, we made Tuoro sul Trasimeno our homebase and visited the rest of the area on day trips by car. Possibly the most amazing part of this arrangement was the fact that our farm stay was so inexpensive while most of the surrounding restaurants were so expensive . Luckily, staying in a house means that you can DIY your breakfast and morning coffee with a beautiful view of the lake, so it ended up being a good deal anyways.

Take a boat ride to the island in the middle of the lake for some hiking and lounging on the beaches.

My number one tip for visiting Italy has to be: bring insect repellant . Everyone in our party ended up with numerous bites, with the poorest of all easily reaching double digits. This is especially bad when you’re staying in a foresty area or near a lake (both of which, of course, we were doing).

Where to eat on Lago Trasimeno

• Il Vecchio Mulino – A favorite of locals, and very affordable spot for pizza and pasta. The prices were a relief compared to many places throughout the area!
• La Badiaccia – Menu only in Italian, but the staff was super kind in helping us to understand what our options are. Food and wine was fabulous and we were even given a bottle to take home!

Yet another hillside town with hopelessly narrow streets – thankfully we weren’t driving an American-sized car or there’s no way we’d have mode it out. There were times when we had mere inches on either side of our rental car, and it was probably dumb luck that we didn’t get any scratches on it! It’s really clear that these cities were not designed with automobiles in mind.

Perugia is special not only for its tiny streets, but the fact that the entire city seems to be made out of stone. There are delicate arches linking buildings together throughout the town, it’s amazing that it’s all still stuck together after the stone has been worn so smooth.

Things to do in Perugia

• Piazza IV Novembre – the main square, you simply can’t miss it!
• Perugia Cathdral – Perugia’s most prominent cathedral

It’s no surprise that Siena was the one city where the number of tourists was still noticable during the shoulder season – its church is OUTSTANDING. I’m not one to care about any ole Italian cathedral, and am the first to admit that they all look pretty similar once you enter the second half of a roadtrip through Italy. But the one in Siena was seriously awesome – known as The Beetlejuice Church , Siena’s cathedral is one of the few that actually takes its stripey pattern seriously enough to apply it to the interior.

Things to do in Siena

• Piazza del Campo – unique central square, shaped like a scallop
• Cathedral Santa Maria Assunta – hands down the most memorable church in Tuscany!
• Facciatone – climb for panoramic views of the tower and the main sqaure
• Lots of shopping on Banchi di Sopra – Siena’s main shopping street

The smooth cobblestone streets shone in the rain and reflected buildings that still managed to be bright and vivid in spite of heavy grey skies. Every shop looked like the platonic Italian market. And of course, high fashion shops mixed seemlessly with the local ones. Lucca, like Italian style, is a mesh of effortless beauty and timelessness. The city’s cohesive color scheme was meant to be immoralized in photos – and you bet I obliged.

Come to Lucca for some of the most quintessentially Italian vibes of the entire trip.

Things to do in Lucca

• Torre Guinigi – Centuries-old oak trees crown this tower, offering lovely views of the city. This tower is probably the most famous sight in the whole city and well worth spending a couple of euros to get to the top.
• Museo Villa Puccini – Puccini is the most famous resident of Lucca, as a renowned Italian composer, he has both a statue in public as well as a dedicated museum.
• Santa Christina – Cute and quirky cafe and enoteca, where I’d definitely recommend popping in for lunch! Lots of nice wine options and decent prices.

Check out my article on more things to do in Lucca, Italy if you’ll have more time in this ultra cute Italian town.

Naturally, you know all about the Leaning Tower of Pisa , possibly the most recognizable building in all of Italy. Pisa has this and more to offer, and is a really popular stop right next to Lucca. Unfortunately I’ve only been to Pisa on a layover, so no pretty photos, but I’d love to go back and do this town justice. Don’t forget it if you’re planning a trip through Tuscany!

Besides Montepulciano, San Gimignano is another popular place to go for wine-tasting in Tuscany. Like many towns in Tuscany, San Gimignano is perched on a hill and has old, medieval houses all throughout its city limits. You can visit its tower, Torre Grossa or enter its most famous church, Duomo di San Gimignano .

Again, somewhere I didn’t get to spend any time but belongs on my next Tuscany Iterary for certain!

Seven tips for a stress-free road trip in Italy

• Get the insurance on your rental car. Italians are known for having a less “gentle” relationship with cars. Get the insurance, at least on the exterior of the car.
• Speed limits don’t matter until they do. Italians often surpass the speed limit and though the fines are high, they’re rarely enforced.
• Save some cash at the pump. Use a self-service station to avoid paying to have someone pump your gas for you.
• Beware of toll roads and closures , both of which are common in Italy – especially if you need to make a deadline in another town, you may face unexpected traffic. Take this into account while planning.
• Getting into small Italian towns by car is tricky. Look for parking before you approach town. Often parking is only available outside the city walls. Parking prices vary greatly depending on where you are.
• Balance your time between small and large towns. Even the touristy spots in Tuscany are well-visited for a reason – don’t pass up the big cities like Florence and Pisa just because you’re worried about fighting the crowds. At the same time, small towns can get repetitive, as each is just as charming as the last. Keep things fresh by mixing and matching!
• Schedule wine tastings in advance. If you’re looking to combine a wine tasting with a meal, booking ahead is absolutely necessary. Without a meal, many wine shops offer less formal tasting (and therefore, don’t necessarily require a reservation).

Have you been to Tuscany or Umbria? If you could pick any of these idyllic towns to visit, which would you pick?

Share your experiences and tips in the comments, I’d love to hear advice on what to do next time!

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About the author

Hi there! I'm Monica, an American expat living in Germany for over six years and using every opportunity to explore the world from my homebase in Berlin. My goal is to capture my memories in photos and posts that show how easy it is to start from scratch and travel the world by working abroad.

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The Perfect Tuscany, Italy Road Trip Itinerary: Florence, Montepulciano, Chianti And More

• Last Updated On: September 8, 2023

Tuscany, the land of wine lovers is an ideal Italian road trip adventure. After traveling through much of the country including road trips through Sicily , Puglia , the Dolomites in the north, the Amalfi Coast , Lake Como , and more, it was time to focus on the ultimate wine region in Tuscany.

Tuscany is probably one of Italy’s most well known areas and has been endlessly referenced in pop culture by movies like Under The Tuscan Sun. It’s not hard to see why. The picturesque rolling hills, beautiful vineyards, and impossibly cute hillside towns make this a bucket list adventure for many travelers.

I spent a week driving through Tuscany drinking my way from north to south. I visited a seemingly endless list of beautiful villages, ate delicious Tuscan cuisine, and watched countless sunsets. This is how I structured my trip and the places I visited. If you’re also planning a trip through Tuscany and are overwhelmed with which villages to visit/stay, and which wineries to drink at, hopefully this guide will help you out!

Where I went in Tuscany

I had one week to spend in the Tuscany province of Italy. I think one week is actually a decent amount of time to explore Tuscany. This includes a stay in Florence, its capital city as well as many nights through its iconic wine regions.

There is not much distance to travel on this trip especially if you start and end your trip in Florence. The wine region is all within a two hour drive from Florence. However, if you plan on visiting many of the smaller towns and wineries, you will spend a lot of time driving just because of the small roads.

When did I visit Tuscany?

I visited Tuscany in the summer season. Summer (July and August) is the high season for a reason as you can expect warm weather throughout the day and lush vines at the wineries. It’s definitely a picturesque time to visit the Tuscany region. However, I visited in 2021 during COVID so the tourism was not even close to what it would be like in normal times.

Having spoken to many Italians working in the region, normal summers pre-COVID are absolute insanity. Entourages of huge tour buses drop off tourists by the hundreds in small towns like Montalcino and San Gimignano. Restaurants and wineries are fully booked weeks in advance so you don’t stand a chance being spontaneous.

These are the places I visited in Tuscany:

• Montepulciano
• Chianti Region including Siena, San Gimignano
• San Quirica D’Orcia
• Wineries all day, everyday, everywhere

If these places ring a bell and sound like the places you want to visit, this is the perfect itinerary for you! Note that there are SO MANY more villages to visit in Tuscany but these were the ones I saw with the time I had. You don’t need much time in each town so if you want to spend less time wine tasting, and more time village hopping, this is also a possibility!

How to get around Tuscany

Unlike other parts of Italy where you can get around by public transportation, you really need to have a car to explore Tuscany. If you’re just planning to visit the main towns like Florence, Siena, Montepulciano etc, then the bus system will suffice. However, if you want to explore the countryside and really immerse yourself in it all, you will need to rent a car.

There are no buses that will drop you off at the Brunello wineries in Montalcino for example. There are no Ubers to speak of in Tuscany and taxis are both expensive and elusive. Essentially, you won’t get much wine tasting in if you don’t rent a car which is probably the main reason you want to come here!

Driving in Tuscany

Driving in Tuscany is both simple and beautiful. The Tuscan landscape is famous for its rolling hills that contrast wheat fields, Cyprus trees, and lush green vineyards. It’s a view you won’t tire of while driving.

The driving is quite easy and the roads are perfectly fine. The distances between places might seem short but make sure to budget more time because you won’t drive more than 70km/hr at most points. Gas is abundant and easily found all along the way.

Where to stay in Tuscany?

I wrestled with where to stay in Tuscany for a long time. Tuscany is not a big province per se but the roads are small so it takes a long time to get anywhere.

I couldn’t decide whether to stay in Chianti and Montepulciano or just stay in one of the two and make day trips.

Ultimately, I settled on doing day trips from Montepulciano which seemed like a central and livelier town. I only had four nights in the wine region so it would feel a bit rushed to do two nights in one place and then have to drive somewhere else.

I don’t regret my decision and found Montepulciano to be a great central point to explore the region.

Wine tasting in Tuscany

Wine tasting in Tuscany is one of the main events you’ll be doing. Tuscan wine is perhaps the most popular wine in Italy and certainly one of the most popular wines in the world. Even when I was drinking boxed wine as a college kid, somehow I had even heard of Tuscany being this magical wine region in Italy that had high end wine that a kid of my stature should definitely not be drinking at the time.

Fast forward a decade later, and here I am drinking my way through Tuscany. And drink I did. I spent five days in the Tuscany area, and each day I would visit two or three different wineries.

How does wine tasting work in Tuscany

Then you go to places like France or Germany where most wineries are smaller shops without a wine tasting infrastructure set up. The bigger wineries require reservations in advance and always include a tour of the cellars that I could care less about.

Some wineries have the whole package which includes the wine tasting, tour of the cellars and property, and bread/cheese. Some of them you could just pay to drink wine. I’m definitely a proponent of the latter because I could care less about touring cellars. I’ve done this countless times already and you just end up forgetting everything anyway.

Cost of wine tasting in Tuscany

Tuscany is not a cheap area to travel. In Italy, it is probably one of the most expensive wine regions simply because of the quality of its wine and the name recognition it enjoys.

Having just visited the Douro Valley in Portugal the week before, it was a bit of a shock to see the prices in Tuscany. Wine tastings are definitely pricier. I was paying €15 or more for tastings of three wines. The quality of the wine tastings are quite good however. There was ample amounts of explanations and information however so I was mostly satisfied.

Some of the fancier wineries definitely exude a sense of arrogance and entitlement whereas most of the wineries I went to were on the more relaxed side with very friendly people (as it should be). I really enjoyed my conversations with some of the people about the wine and just about the culture in the area.

Tuscan Wine Summary

Tuscan wines specialize in the San Giovesse grape. This grape is found all over Italy but its most cultivated in Tuscany. Tuscany wineries mostly grow the San Giovesse grapes along with numerous other varieties. The wines in Tuscany mostly focus on this grape.

The biggest regions in Tuscany are

Each region produces wines with the San Giovesse grape but each region has different standards and requirements for the higher end versions of their wines. There are too many rules and requirements to speak of so I will just list some of the most interesting ones:

• Nobilo Di Montepulciano : The wineries here make Nobilo which is 85% San Giovesse minimum, and has to be aged for two years
• Brunello di Montalcino : The most famous wine in the region is without a doubt Brunello. These have to be 100% San Giovesse, hand picked, and must be aged for five years. Yes,  5 years. 
• Chianti Classico : The highest grade of Chianti requires 80% Sangiovese grape, and must be aged for a minimum of 12 months. Reservas must be aged 24 months.

Full Tuscany Trip Itinerary

Of course, if you have not been to Rome before and have closer to two weeks to spare, then I would definitely recommend visiting Rome for at least 3-4 nights.

From Rome, I rented a car and drove north through Umbria and into the province of Toscana (Tuscany). On the first day, I stopped in the town of Orvieto for a few hours before arriving at my destination for the next four nights in Montepulciano.

From Montepulciano, I spent one full day exploring the wine around the area including which produces Rosso Di Montepulciano and Nobile wines. In the same day, I drove west to Montalcino (30 minutes or so) and sampled the famous Brunello di Montalcino wines. These were amazing.

The next day, I spent the entire day exploring the Chianti region in the north. I stopped at a few wineries and visited the towns of Siena and San Gimignano. Definitely need to start early for this one.

From Florence, I flew back home as this was the end of the trip. If I had more time, I would have definitely continued on to Cinque Terre as that is just a short train ride away.

Day 1: Orvieto and Montepulciano

The trip starts in Rome. Again, I only flew into Rome to start the trip as it was the best international flight option.

Had I not been to Rome before, I would definitely spend at least 3 nights here to see the endless sights and history the city has to offer. Nevertheless, the Tuscany adventures must go on.

From Rome, I picked up my rental car from  Noleggiare car rental and was on my way northward. The first destination is Montepulciano but as I arrived in the morning, I had most of the day to explore. I stopped in the town of Orvieto as I had heard many good things about this historical town. It’s actually not in the Tuscany province but rather that of Umbria.

Orvieto Town

Orvieto is home to incredibly beautiful and quaint Italian architecture. With its picturesque buildings and cobblestone streets, simply walk around the town and get lost in its little alleyways. Before you know it, you’ve come across the stunning and large Duomo that dominates the town. This Duomo is definitely one of the more stunning cathedrals in Italy. The detailing and murals in its facade are breathtaking.

The cathedral is over 800 years old and as you’d expect in Italy, is in as great of condition as ever. It costs €4 to enter and well worth the visit.

Visit the Belltower of Orvieto

No Italian town is complete without a bell tower. Make your way back onto Corso Cavour to head to  Torre del Moro . This tower offers the most breathtaking 360-degree views of Orvieto and is absolutely worth the €2.80 entrance fee. The best part? There is an elevator that takes you half way up so you don’t have to walk like a chump, and then you climb the last stretch of stairs to get to the viewing platform.

Arriving in Montepulciano

After having lunch in Orvieto, it was time to drive towards Montepulciano. If I wasn’t so tired, I would have probably just visited Pilignano on this day and checked it off the list. Instead, I saved that for a few days later in the trip.

Montepulciano is probably the biggest village/town in Tuscany. I consider Siena and Florence to be cities but among the cute must see traditional villages, Montepulciano is the biggest.

Montepulciano is one of many hilltop towns in Tuscany. Its beautiful Medieval buildings located on the top of a hill makes it incredible to look at from afar. While in the town, there are beautiful street after beautiful street for you to walk through.

Make sure to make a reservation at Osteria Acquacheta which is famous around the region and serves a delicious Bistecca Florentina. The pastas are also incredible here so make sure to try the pasta with tartufa (Truffles).

Day 2: Montepulciano and MOntalcino

The day is long so make sure to have an early start. Wineries open between 9:30 and 10:00am on most days.

Wine tasting at Bindella Winery

The first stop is the Bindella winery which came highly recommended from my Airbnb host. This winery is one of the biggest and grandest wineries in the Montepulciano region. It is modern, spacious, and has absolutely spectacular views of the Tuscan landscape with a beautiful tasting room overlooking it.

We just showed up without a reservation and had our first of many tastings of Tuscan wines. Being in Montepulciano, I learned all about the wine production here and about the Sangiovese grape. I tasted a basic Rosso Di Montepulciano from Bindella, as well as their higher end Nobilo wines.

Delicious, and beautiful views without a doubt. The tastings are a bit pricey however at 21 euros.

Lunch around Pienza

One of the best places to try Pecorino is at the Cugusi Silvana farm. Located right outside of the town, this farm produces pecorino and has an onsite shop that provides tastings as well as the ability to create your own picnic basket. Once you’ve selected your cheese and meats (I’d recommend tasting the more aged pecorinos), you can take it and enjoy it on their properties which have stunning views of the Tuscan landscape.

This is every Italian lovers dream. Eating outside on the rolling hills of Tuscany enjoying a glass of Montelpuciano while eating delicious bread and cheese.

Montalcino Town

Next stop, wine tasting of Brunello!

Azienda Agricola Patrizia Cencioni – Brunello di Montalcino Winery

I must say I really lucked out when discovering this winery located just outside of Montalcino.

I ended up buying a few bottles because Brunello di Montalcino bottles outside of Tuscany can be very expensive.

San Quirico D’Orcia

Had a quick aperitivo here before heading back to Montepulciano for dinner.

Day 3: Chianti Region

The next day was focusing on exploring the Chianti wine region of Tuscany. Chianti is the largest and most well known of the areas in Tuscany. It produces about half of the total wine output of Tuscany.

There are also countless wineries in Chianti to choose from so of course one day is not nearly enough to experience everything.

Castello Brolio

The grounds of this castle are beautiful, albeit not as pretty as the castles I’ve become accustomed to living in Germany . Nevertheless, the views from the winery are absolutely gorgeous. You can see the whole valley of Chianti here.

I will say that I found the landscape near Montepulciano and Montalcino more picturesque than in Chianti. You will not go wrong in either place however!

La Lastra Winery

Next stop was a wine tasting at La Lastra Winery just outside of the town of Siena. This winery was one of the first BIO wineries in Italy. The owner came and gave us a fantastic wine tasting giving us hearty pours and very descriptive explanations.

The property was also fantastic and screamed of Tuscan charm.

For lunch, I decided visiting Siena was a must. Siena is the second largest city in Tuscany after Florence and makes for a very easy day trip.

Montecchiello Viewpoint Point

If you have time and energy, make sure to go to the ultimate viewpoint in Tuscany that shows off its natural beauty. This is the “famous” Cyprus tree lined road that winds and curves around to a beautiful farmhouse estate.

This is actually a hotel you can stay at but most people stop here to take beautiful photos of the landscape.

Day 4: Pitigliano

The following day started with a drive south to the beautiful hold town of Pitigliano. Located on top of a hill (which city in Tuscany isn’t at this point?) this town had old school charm that kind of reminded me of my visit to Matera in Puglia. 

The town itself is not that big and there are only two main streets to walk through. However, the streets are very pretty as well as the views of the nearby valley.

I think looking back on it, I probably would not come to Pitigliano as a day trip from Montepulciano. It is quite far and not worth going all that way for. The weather was particularly bad on this day so I ended up calling the day early.

If I could go back, I would probably just spend another day driving around the Val D’Orcia and visiting the wine regions I wanted to see. I particularly liked the Brunello wines from Montalcino and I would have spent more time there.

My original plan was to actually go to Pitigliano and then to a winery in the Montalcino area like Banfi winery specializing in Brunello.

Terme Di Saturnia

If the weather was nicer, I would have surely visited the Terme Di Saturnia which are the famous and ultra picturesque thermal pools of Tuscany. However, with these places, I suspect the pictures are almost always better than reality. The pools look absolutely amazing given the right filters and the absence of crowds. Just look at this drone photo!

If this doesn’t make you want to visit, I don’t know what will. Sadly, this place gets super busy in the summer months. I think I would only come and visit this place during the off season months, and I would only come here right as the sun rose to avoid the crowds.

Day 5: Antinori Winery, San Gimignano

It’s a modern architectural wonder and also home to its wine shop where you can taste the many wines Antinori has to offer, as well as a Michelin style restaurant with beautiful views of its vineyard.

Antinori has multiple labels and multiple brands of wine in many locations around the world which was a big change from the smaller wineries I had visited previously. This place is famous for wine tasting tours with their cheapest tour option starting from €35 a person. However, if you do not want to book a scheduled tour, anyone can show up and walk around the estate and enjoy wine tastings at their leisure. This place is expensive however so keep that in mind.

San Gimignano Town

San Gimignano is an old fortified medieval town whose walls date back to the year one thousand. It is famous for its historic and artistic heritage and its architecture, especially its towers. In 1990 it was declared a World Heritage Site by Unesco. Also very popular its local products including saffron and white wine, Vernaccia di San Gimignano.

This is probably one of the, if not the most picturesque town I saw in Tuscany. Highly recommended for a quick stop before going to Florence.

Day 5-8: Florence

Last but not least, the trip ends in Florence, the capital of Tuscany. Florence, as many might know from history classes, is one of the most important cities in Europe and the birthplace of the Renaissance. The Medici family, whose name I heard so much of in high school history, more or less ruled Florence for centuries and helped cast the Renaissance movement that took over the rest of Europe.

Eat Paninis in Florence

Florence is famous for their paninis, an in particular the Schiacciata bread. When in Florence, no trip is complete without gorging on many of these oversized sandwiches.

The most famous place of all is without a doubt All’Antico Vinaio. This place is an institution in Florence and attracts thousands of people every day to eat their sandwiches. The sandwiches are stuffed with meat, cheese, and veggies depending on your preference. All of it is then pressed and warmed between two pieces of Schiacciata bread, which I can compare to Focaccia bread.

All’Antico Vinaio attracts lines that can wrap around the street. On my first visit, I came around 1pm which is rush hour. The line was wrapping around the corner so I decided to come back the following day around their opening time of 10am. There are multiple locations of All’Antico Vinaio literally on the same street (that’s how much demand there is) but all of them fill up with hungry tourists and locals alike.

After waiting about 15 minutes, I was able to finally purchase one of these delicious sandwiches. I went with the original Favalosa and the thing is massive. Bring it with you to the river nearby and enjoy your sandwich with a view. It’s likely there will be many others near you also doing the same thing.

Alternatively, if you don’t want to wait in line, I had paninis in other institutions nearby. I can recommend Panini Toscani and Il Bufalo Trippone. Both sandwiches are delicious and on the cheaper side (€5 or so).

Eat Florentine style steak

La Bistecca Florentina is an  absolute must eat when visiting Florence. Turns out the city is also famous for its exceptional cows and steak. There are numerous restaurants in the city that serve the famous steaks which are essentially extra thick porterhouses.

The steak is incredibly tender and juicy. More tender than most other steaks I’ve had with the exception of Japanese Wagyu of course .

What to do in Florence

This deserves a post in its own right and I might just make one eventually. There are so many things to do and see in Florence. Here are my main highlights of the city

• Go to the Duomo: You can’t miss this. You literally cannot. It is in the center of the city and its huge dome is visible throughout the city. The pictures are also very stunning of the narrow Florence streets with the Duomo at the end
• Piazza Michelangelo: For the best views of the city, go to the Piazza Michelangelo and enjoy the sunset with some drinks
• David of Michaelangelo:  The ultra famous Statue of David sculpted by Michaelangelo is in this museum. Try to visit right before closing time to avoid the crowds
• Ponte Vecchio:  Famous arched bridge with Roman origins. Definitely a must see.

Here are some more pictures to help inspire your Florence trip.

Day 8 or 9: Pisa

I actually had a flight booked out of Pisa Airport which is 1 hour west of Florence since that is the Ryanair hub. There were many cheap flights to Frankfurt and other European cities that it made sense for me to take this flight home. Along the way, it only makes sense to stop in one of the most visited and well known tourist attractions in the world, the leaning tower of Pisa!

If you are not flying out of Pisa, simply make a day trip from Florence. The trains leave from the Florence central station frequently and takes 1 hour to get to Pisa. From Pisa train station, it is a 20 minute walk to the famous leaning tower of Pisa.

If you are flying out of Pisa airport and want to visit on your way out but worried about your luggage, there is a luggage storage option just outside of the main station called Stowaway Lockers.

There’s not much to say about the Leaning Tower of Pisa that you don’t already know. It was originally designed to be a bell tower in the 12th century. The plan was to never build an actual leaning tower, but it only progressed in this manner while it was being built. Floor after floor would go up and people noticed the lean to horror and dismay. Eventually, they just left it leaning and it still stands today as the penultimate symbol of Pisa.

Make sure to take your standard perspective photos here of you pretending to hold it upright, kissing it, etc.

Of course, there will be hundreds of other people doing it too which always makes for a good photo in and of itself.

Tuscany Itinerary Day by Day

This is my Tuscany itinerary on a day by day basis to summarize everything that I wrote. I will also give you some ideas for other itineraries depending on your allotted times!

Remember that I stayed in Montepulciano for the duration of my stay in the wine region. If I had more time, I would have split my stay between Montepulciano and a town in the Chianti region so I could explore the areas easier without driving so much. I will give numerous options below to inspire!

Rome to Florence – One week

Day 1: Arrive in Rome, drive to Orvieto for lunch and then arrive in Montepulciano Day 2: Wine tasting in Montepulciano area, lunch in Pecorino Farm, afternoon in Montalcino and wineries around the area Day 3: Drive to Chianti and visit wineries in the region, lunch in Siena Day 4: Full day of wine tasting in Tuscany Day 5: Montepulciano to Florence, stop at San Gimignano and Antinori Winery along the way Day 6: Full day Florence Day 7: Full day Florence Day 8: Pisa day trip, fly out of Florence/Pisa

Florence to Florence – One week

Day 1: Arrive in Florence, explore city Day 2: Full day in Florence Day 3: Day trip to Pisa and Lucca Day 4: Drive to Antinori Winery and San Gimignano, overnight in Montepulciano Day 5: Explore Montepulciano and wineries surrounding Day 6:  Explore Montalcino and the Brunello making wineries of the region Day 7: Free day to explore the Tuscan wine region Day 8: Drive back to Florence to fly home

Florence to Florence – Ten days

Day 1: Arrive in Florence, explore city Day 2: Full day in Florence Day 3: Day trip to Pisa and Lucca Day 4: Drive to Antinori Winery and San Gimignano, overnight in Siena Day 5: Explore Chianti Region wineries Day 6:  Drive to Montepulciano while wine tasting along the way, overnight in Montepulciano Day 7: Explore more of Montepulciano Day 8: Explore Montalcino and wine region around Day 9:  Day trip to Pitigliano and the villages nearby Day 10:  Drive back to Florence

Florence to Florence – Two Weeks

With two weeks, I think you can really do the region justice. I would also include Cinque Terre as this is an incredibly beautiful and well known spot that is nearby to Florence.

Day 1: Arrive in Florence, explore city Day 2: Full day in Florence Day 3: Full day in Florence Day 4: Drive to Pisa and Lucca, overnight in Cinque Terre Day 5: Full day Cinque Terre Day 6:  Full day Cinque Terre Day 7: Drive back towards Tuscany and overnight in the Chianti area (San Gimignano, Siena, etc.) Day 8: Wine tasting in Chianti region Day 9:  Drive to Montepulciano, wine tasting along the way Day 10:  Full day wine tasting in Montepulciano Day 11: Full day wine tasting in Montalcino area Day 12: Full day wine tasting in your preferred area Day 13: Day trip to Pitigliano and Terme Saturna baths Day 14:  Drive back to Florence to fly home

Tuscany and Amalfi Coast Itinerary

Tuscany and the Amalfi Coast of Italy are perhaps some of the most desirable locations to visit in Italy. I am a huge fan of the Amalfi Coast and absolutely love the city of Naples.

Once you’re done with wine tasting Brunellos in Tuscany, then traveling to the birthplace of pizza in Naples is the logical next step right? Round it off with a visit to the wonderful island of Capri and the incredible views on the Amalfi coast and you have the ultimate Italian itinerary.

I spent a week traveling around Tuscany and about ten days in Naples and the Amalfi Coast. If you have two to three weeks for your trip you can easily do this trip by combining the itinerary in this post, and the itinerary from my Amalfi Coast itinerary .

Something like this:

Day 1: Arrive in Florence, explore city Day 2: Full day in Florence Day 3: Day trip to Pisa and Lucca Day 4: Drive to Antinori Winery and San Gimignano, overnight in Montepulciano Day 5: Explore Montepulciano and wineries surrounding Day 6:  Explore Montalcino and the Brunello making wineries of the region Day 7: Free day to explore the Tuscan wine region Day 8: Drive to Florence and fly to Naples Day 9:  Full day Naples Day 10:  Full day Naples Day 11: Naples to Capri Island Day 12: Full day Capri (Anacapri and Capri) Day 13: Full day Capri (Anacapri and Capri) Day 14:  Capri island to Positano Day 15 : Positano & Praiano Area Day 16 : Positano & Praiano Area Day 17: Ravello Day 18: Ravello Day 19 : Ravello Salerno to Naples

Of course you can shorten or lengthen this itinerary depending on your time frame but it is totally doable!

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Tuscany travel blog — the fullest tuscany travel guide for first-timers.

Those who have been to Florence, definitely must have heard of the poetic countrysides of Tuscany (Toscana in Italian), Italy. Cycling around Chianti, enjoying premium wine, or visit the vast countrysides of Siena. But actually, the most beautiful countrysides in Italy are located quite deep below, they are Val d’Orcia and San Quirico d’Orcia which are always covered with a endless green color of meadows, vineyards and beautiful farms on highlands and in valleys. So, what to do and how to plan a perfect budget trip to the dreamland and paradise of Tuscany for the first-time? Let’s check out our Tuscany travel blog (Tuscany blog) with the fullest Tuscany travel guide (Tuscany guide, Tuscany tourist guide) from how to get there, best time to come, where to stay, best places to visit and top things to do to find out the answer!

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I never intended to go to Tuscany when knowing this is just the central Italian countryside, until I accidentally came to Florence and got lost in the scenes of villages, medieval towns, vineyards, olives groves with wineries, lush green vegetation. Tuscany instantly captivated me so that the first days of summer were surprisingly beautiful.

Tuscany travel blog: Overview of Tuscany

I have known Tuscany since I was a landscape photographer. That’s when I got to see the amazing photos of Val D’Orcia and San Quirico D’Orcia. If the natural beauty of Switzerland with mountains and rivers, then in Tuscany, it is majestic, poetic countryside, immense grasslands. The natural picture here is green in one color, gentle, tranquil and liberal, enough to inspire any lover or dreamer when coming here.

Tuscany blog: When to visit?

There are two beautiful times to consider for a roadtrip in Tuscany, which is from late April to mid-May, and autumn in Europe. In spring, flowers bloom everywhere in Tuscany, which is perfect for visiting the farms or large gardens. If you go in the fall and want to see the vast green prairies, you should go in early August, because at this time, local people will start cutting the grass and harvesting grapes. Then the hills will appear with a dry yellow color and not smooth.

• If you want to see sunflower fields, you must go after June and before September. From early September onwards farmers have already harvested seeds to make oil.
• The most beautiful time with green fields is around June and July. From August onwards, it has started to dry. From September onwards, the scenery have turned to yellow but romantic. However, July and August are the hottest months in Italy. You must bring sunglasses, hat and sunscreen. In the summer, even though it’s really hot, it will get colder in the evening. Especially if you go higher areas.
• In addition to summer, traveling to Tuscany from March to May is also okay, very green. However, it is still cold and there are no flowers at all.

Tuscany travel blog: Where to go, what to do?

To start exploring Tuscany, Florence is a must-visit destination. The capital of Tuscany in central Italy, Florence owns everything to be voted by many prestigious travel magazines as the most wonderful city in Europe. The whole city is a giant architectural style with pastel colors of walls and terracotta roof tiles of houses, each street corner seems to be a museum with untold stories. Florence deserves many fine words. If you’ve been here, you can’t help but visit the Florence Cathedral Duomo(Cathedral of Santa Maria del Fiore), the legendary Ponte di Vecchio, the Galleria dell’Accademia, and the Piazzale Michelangelo square.

From Florence, you can travel by train to many ancient cities and towns in Tuscany, or just 30 minutes by car, you can visit a nearest olive grove and vineyard. If your time is tight to make an itinerary, as Tuscany’s most developed tourist city, Florence offers you everything with countless day tours to pick and explore all of Tuscany.

Siena used to be a large city in the Middle Ages, so the architecture of Siena is still keep intact. In the middle of the city is the town hall with the horse racing square, every year the small districts in the city will bring their horses here to race to win glory for themself. If you go to Siena on Saint Catherine’s Day on April 29 every year, or the horse racing day, the districts of the city will hang their own flags. I was lucky enough to come to Siena on the occasion of St. Catherine’s day, so I saw countless flags hanging along streets, alleys, feeling like I was watching Game of Thrones.

Things to do in Siena include tasting the region’s famous Chianti wine, visiting Piazza di Campo square, Siena’s church which made entirely of marble and don’t forget to go inside the church to explore the Piccolomini library which is built by Pope Pius II. The architecture inside is overwhelming and for me this is the most beautiful church I’ve been visited in Europe.

San Gimignano

A medieval town with 14 towering stone towers. In medieval times, San Gimignano was likened to today’s Manhattan in terms of prosperity. San Gimignano is quite small so you can explore in an afternoon. But don’t forget to climb a tower for a panoramic view of Tuscany to the horizon.

To explore Siena & San Gimignano, you can book a tour in Florence, or book a tour through KLOOK , I found that when buying from KLOOK the price is cheaper, so just book it and the service is very good.

Located in Umbria, Assisi is a beautiful hill town. When hearing about a place that has existed since the Middle Ages, surely many tourists will think of a town forgotten by time, not very developed with narrow winding streets, narrow alleys, houses with stone walls and old painted wooden doors. However, unlike the imagination above, Assisi is one of the largest Christian centers in the world with beautiful churches. In which Basilica of San Francesco d’Assisi (Basilica di San Francesco d’Assisi) is the most famous cathedral in Assisi.

This ancient city is also known as a student city because there are many universities and colleges with many different disciplines. The most prominent is the University of Perugia, built in 1308, the University for Foreigners of Perugia and many other colleges such as the Academy of Fine Arts Pietro Vannucci.

Perugia is also famous as a cultural and artistic center of Italy with many festivals taking place all year round such as EuroChocolate festival, Umbria Jazz Festival, International Journalism Festival, …

Lake Trasimeno

When you come to Trasimeno, you can rent a house on a farm and experience the feeling of waking up in the sunrise of the Italian countryside. Make yourself a cup of hot coffee and make a delicious and light breakfast while enjoying the poetic beauty of Lake Trasimeno.

After that, you’ll have a full day of exploring and boating on the lake. If you go in a large group, you can also organize a picnic with dishes made from fresh ingredients at the farm.

Montepulciano

Although Montepulciano is a small town, the scenery here is extremely poetic and beautiful with brilliant sunflower fields. In addition, wine is also a famous specialty here. If you have stopped by Montepulciano, then come and enjoy wine at the bars here.

Like the Italian style itself, Lucca has a beauty that blends the modern and the antiquity of the time with fashion boutiques interspersed between immaculate ancient structures.

Lucca is also home to many famous composers such as Giacomo Puccini (with famous works of La Bohème and Madama Butterfly), Nicalao Dorati, Francesco Geminiani, Gioseffo Guami. With such a history, it is not surprising that the annual Lucca Summer festival is one of the most popular musical events in Tuscany.

In addition, Lucca is also the host city for the Lucca Comics & Games Festival, the biggest festival for comics, movies and games in Europe, attracting hundreds of thousands of fans to attend each year.

Pisa is a port city in the lower reaches of the Arno River. In Renaissance Period, Pisa was the second richest city after Florence. Today Pisa is a small city but has a unique artistic style and owns a unique architectural symbol in the world: the Leaning Tower of Pisa. From Florence, you take the 50-minutes train to get to Pisa. Then follow the flow of people to the Leaning tower of Pisa to visit.

The Leaning Tower of Pisa itself is so famous but it is only part of Pisa’s Central square. Visitors come here mainly just to take hundreds of pictures from the simple to the weird with the Leaning Tower. Personally, I like architecture, so I wandered around to see this small, sparsely populated city to understand more about the most important port city in Tuscany.

Not all of Tuscany’s hills and vineyards have the stunning coastline below. But Punta Ala is a great stop on the coastal area known as La Maremma.

Island of Elba

Elba Island (Isola d’Elba) is a romantic tourist island, located off the coast of Tirreno Sea, in the famous Tuscany country. Looking at Elba from above, you will have the feeling that the island looks like a small goldfish swimming in the sea.

Portoferraio – the main port town and also the capital of Elba – looks cute and gentle with its small houses painted in soothing pastel colors. The streets here are narrow, on both sides of the roads there are many colorful flower pots swaying in the wind, only the slopes are more pleasant than other central Italian cities such as Perugia, Siena, Assisi or Spoleto.

Enjoy Tuscan wine and olives

The Tuscan countryside can be seen from car, but to get a real taste of it, visit a winery and sample its fine wines. I stopped by Tenuta Torciano Winery and not only enjoyed more than 7 types of red to white wines but also used delicious vinegar and olive oil. These farms are not open to a single tourist, so you can book a tour in Florence to visit during the day, definitely a true Italian experience. There are two famous and savory Tuscan wines you should try called Sangiovese and Super Tuscan.

To experience this, you can buy a day tour in Florence, or book online through KLOOK to explore both San Gimignano and Siena.

Buonconvento

Buonconvento is a small town, just about 2-2.5 hours drive from Florence, this town is extremely peaceful, few people but has a lot of interesting things. It takes about 10 minutes to drive from Silvia’s farm (where I stayed) to the town center. Everything here is as peaceful as countrysides around it.

Another interesting thing not to be missed in this beautiful little town of Buonconvento is the delicious Gelato ice cream that we discovered located right next to Da Mario restaurant. Not only has delicious ice cream, but the salesman is also very cute, giving customers a lot of ice cream, the best Gelato I have ever tasted in Europe, the price is also cheaper than in other regions.

More things to do in Tuscany

In addition to visiting the Tuscany lush green prairies, there are many other places here that you cannot miss. It could be touring the small towns of the region, or going to the vineyards to enjoy fine wines.

Another route that you should refer to when traveling from Siena to Buonconvento is going through Asciano (please see on the map). On this road, the scenery on both sides is also extremely beautiful. The day I went, the grass here was almost cut, so the color could not be as beautiful as in the southern region. Alternatively, on the way from Buonconvento to Asciano, you can visit the Abbazia di Monte Oliveto Maggiore monastery. This is a monastery located on a high mountain with a beautiful view.

Another very beautiful place that you might consider visiting is La Foce garden located in Val D’Orcia. Entering this garden, you will feel like walking in a large royal garden of a palace, like a mix of Versailles palace and Tuileries Garden. In La Foce, the owner also has villas for rent, but the price will be quite high and require a minimum stay of 2 nights for each booking.

In general, with a travel time of only 2-3 days, it is difficult to fully enjoy the vast Tuscany region. If given the opportunity and conditions, I would love to stay longer than about 1 week. This place is extremely suitable for those who come with family, a fresh air and spacious space for everyone to experience together. Simply rent a large enough SUV, free to explore each road, small villages but hidden full of interesting things in this Tuscany region.

Tuscany travel blog: What and where to eat?

Enjoying pasta, pizza and wine as well as Tuscan cuisine is a fascinating experience you can’t miss! Like Italian cuisine in general, Tuscan cuisine is based on the use of the freshest and simplest ingredients of season including a variety of beans, cheeses, vegetables and fruits. And here are some suggestions for you:

• Crostini Toscani: The word crostini literally means bread, similar to a baguette, served with chopped chicken liver sauce.
• Panzanella (Tuscan-Style Tomato and Bread Salad) is a cold bread salad with the main ingredients including unsalted bread, tomatoes, red onion, basil, olive oil, vinegar, and salt.
• Lardo di Colonnata: This dish is actually pork lard produced in the town of Colonnata.
• Ribollita: Ribollita soup is one of the most popular winter dishes in Tuscany containing different types of cabbage, beans, onions, and carrots.
• Castagnaccio: It is a traditional Tuscan chestnut cake made with chestnut flour, very popular in the Apennine mountain region of Tuscany.

Tuscany blog: Suggested 2-day Tuscany roadtrip and how to get from Florence

As mentioned above, you can take the train to the countryside in Tuscany, but it will be quite inconvenient and take a long time. The most convenient is to rent a car in Florence and then self-drive to the south, through Siena and visit its beautiful countrysides. Rentingg a private car to drive can both be proactive in the schedule while you can go and admire the scenery on the roadside, stop whenever you like.

Details of my 2 day Tuscany itinerary:

Day 1: Took the car from Florence and drove down to Buonconvento, where I booked an overnight stay at a local farm. The itinerary will have to go through Siena so you can choose to go straight on the highway to Buonconvento because my main purpose is to visit Val D’Orcia. If you have time, you may not choose the highway but follow the SR222 road to visit more Panzano or Chianti. Dinner in town and overnight in Buonconvento.

Day 2: Early morning drive to visit two regions Val D’Orcia and San Quirico D’Orcia, which have the most beautiful scenery in Tuscany (in my opinion). Then come back, resting and exploring the farm Podere Salicotto that I chose as a place to stay. On the drive back to Florence I took the route from Buonconvento through Asciano and back to Siena to access the highway to return to Florence.

The route from Florence to Buonconvento has many stops to admire the beautiful scenery on both sides of the road. If your time is tight, you should choose the highway to go for faster, the traveling time for a 150km distance is only about 2.5 hours, the highway is very beautiful and the speed is stable.

After picking up my car from Locauto rental company I started driving out from the center of Florence. The street was not too crowded and easy to go, so you can rest assured, just go according to the law. Follow Google Maps and get out of the city to access the highway. From here running straight to Siena and continue to Buonconvento. One thing to note is that if you want to be fast, you should only take the highway, and you need to pay attention to the road because it is easy to go wrong on roads in town, make the speed will be slow a lot because these roads have many traffic lights, many cars make you cannot go as fast as on the highway.

Tuscany blog: Where to stay in Tuscany?

However, coming to Tuscany, you must stay at a beautiful farm in this region.

Along the romantic swath of Tuscany are vast countrysides known for its rolling hills, cypress trees, charming old towns, stone castles and along with numerous private farms. Each farm with hectare area with quite similar architecture. Houses are built of red bricks or can be called separate villas. It took me a whole week to choose for myself the best place to stay, which is Podere Salicotto’s farm.

I had a very detailed review of this property here , it’s very wonderful, you can also refer to and book via Agoda.com or Booking.com .

The capital of Tuscany is Florence, so it has the largest number of rooms of all types and vary prices as well as making it easy for you to travel to many cities, towns nearby, choose the right day tours to explore beautiful Tuscany. Plus, if you want to try the local experience, it’s also easier to rent an Airbnb in Florence when you’re sharing a house with a local.

But if you like the feeling of waking up in the countryside, Siena is the better choice because the city is small and located among the vast fields of Tuscany.

You can find more, check rates, availability & book for hotels in this city on Agoda.com or Booking.com .

Tuscany travel guide: Getting to Tuscany

You should go to Florence first because it offers many choices of hotel rooms and also convenient to travel to its surrounding areas. Florence’s services are also easy to find and relatively inexpensive. Buses can be booked at GoEuro.com and train tickets can be purchased at booths at the central station, choose Treinitali or Italo train.

Take a day tour from Florence

I recommend taking a tour to Siena because the cost is quite cheap but there are many interesting experiences for only 44 euros. In addition, you can book a tour to Cinque Terre to explore the equally wonderful Liguria region.

Tuscany blog: What to buy as a gift in Tuscany?

Florence is very famous for its leather goods, you just go to the ancient bridge, there are many leather goods shop with hundreds of years old to buy. In addition, Chianti red wine is also a popular choice.

Souvenirs such as statue of David or the leaning tower of Pisa are also things that tourists often buy as gifts.

Some best day tours, trips, activities and transfer services, tickets in, from and to Florence you can refer to

• Duomo Monumental Complex Direct Access Ticket in Florence with Guided Visit
• Florence Duomo, Baptistery, and Museum Tour
• Small Guided Tour with Fast Track Entry to Duomo and the Secret Terraces
• Florence Duomo Skip-the-Line Tour with Balcony & Dome Access
• Uffizi Gallery Guided Tour with Fast Track Entry
• Accademia Gallery Skip-the-Line Ticket in Florence
• Val d’Orcia Tour from Florence
• Pisa Half Day Tour from Florence
• Florence Bike Tour with Food Tasting Experience
• Florence City Sightseeing Hop-On Hop-Off Tour (Open Top) and Leonardo da Vinci Museum Skip-the-Line Ticket
• Tuscany Day Tour with Lunch and Wine Tasting from Florence
• Rome to Florence Day Tour
• Chianti Afternoon Tour from Florence
• Excursion to Pisa through the Tuscan Countryside from Florence
• Florence Dome Tour with Skip-the-Line Ticket + Free Souvenir Old Polaroid Photo
• Florence Accademia Gallery Skip-the-Line Ticket with Tour

Are you looking for more top things to do in Florence: Tours, activities, attractions and other things? Let’s check it out here . And Italy travel guide here .

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Key to the #BestTripEver

The best articles on traveling to tuscany.

Tuscany occupies the center of the Italian boot and is home to the country’s most picturesque countryside views. It can be visited during a day trip, long weekend, or even a longer trip including rental property. This page was created with the specific intention to make planning a trip to Tuscany easier.

Top Day Trips to Tuscany & Wine Tours

Paris is a city of great culture and even greater history. It has long been the capital of France and while Brussels takes the official title, Paris has been and remains the unofficial cultural capital of Europe. A city like this comes to life with local guides. All of a sudden, you know every story, every crossroad, where to eat, and what to do. Museums go from beautiful artwork to stories of the French Revolution. Our tours will elevate your experience in Paris and make your trip more memorable.

Chianti Day Trip from Florence with Vineyard Lunch

Want to have an epic experience in Tuscany? Remove the guesswork and logistics by joining us on a day trip to Chianti from Florence including Siena. Transportation, lunch, and lots of wine included!

Uffizi Tours

Choose a small group or private tour to see the former offices of Medici that now hold one of the greatest museums on Earth.

Accademia Tours

Seeing Michelangelo’s David is a bucket-list item but tickets are limited and the story behind the statue is vast.

Latest Tuscany Articles

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Continue Reading The Best Vineyard Hotels in Chianti in 2024

The Best Tuscany Tours To Take in 2024 and Why

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Continue Reading The Best Tuscany Tours To Take in 2024 and Why

Top Things to Do in Tuscany

Dreaming of a trip to Tuscany and want to get a head start on planning? We don’t blame you! The region is one of the most beautiful and popular destinations in Europe, with a huge amount to see and do. In this guide, discover the top things to do in Tuscany for a memorable trip.…

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Where to Stay in Arezzo, Tuscany in 2024

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Where To Stay In Pistoia in 2024

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WHERE TO STAY In and Near SIENA, TUSCANY in 2024

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Where to Stay in Lucca, Tuscany in 2024

Italy is as crowded as I have ever seen it. While cities like Florence, Rome, and Venice should be on anybody’s list of destinations in Italy, her sister cities are worth a look when choosing a base from which to explore. Enter stage right the lovely Lucca. A gem in the heart of Tuscany, I’m…

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The romance of a Tuscan road trip

Key in the ignition, winding roads through olive groves, vineyards and ancient villages ahead… Get revved up for the Italian drive of a lifetime

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Halfway through our Tuscan road trip, between two famously beautiful drives—the Val d’Orcia and the Via Chiantigiana—we find ourselves lost. Part of the route we had plotted is temporarily closed, so we follow our noses, and soon we’re bumping down a strada bianca , a white road, so-called because they’re unpaved, the dusty gravel crunching under our tires and leaving a cloud in our wake.  But this is far from a disaster. This region of Italy is famed for many things: Its ancient cities of Florence , Siena and Pisa , rich with Renaissance art and iconic architecture. Its world-class wine. Its prized truffles and pasta. Its distinguished designers. And then, of course, there are its astonishingly beautiful landscapes where, around each snaking turn, you’ll find yet another breathtaking view of a verdant valley or historic hilltop town.  

Our journey begins and ends in Florence, a city that is becoming increasingly pedestrianized—and harder to drive into, with one of Italy’s many urban zone a traffico limitata (limited traffic zones), where fines are easy to accumulate. So, rather than picking up our rental car from Florence Airport straightaway, we hop on one of the cheap, speedy trams into town, and spend our first 24 hours cramming culture (the Uffizi Gallery ’s Botticelli paintings), vintage shopping (San Spirito’s superb market) and sunset aperitivi (snacks and spritzes at Hotel Continentale ’s chic rooftop bar, La Terrazza, with its views across the River Arno). 

The next morning, we return to Florence airport to pick up our rental car, and are soon on the road. We’ve plotted a clockwise loop, a jagged oval skewing south southeast. Our first destination is Montepulciano , a hilltop town famous for its wine, on the western edge of the Val d’Orcia, a valley so beautiful it’s been made a UNESCO World Heritage Site. Barely are we on the highway, however, before my copilot declares we need to make an emergency stop: a very worthwhile seven-minute detour to The Mall Firenze , a temple to every major Italian designer, with deep discounts and a clientele so chic, we even spot a baby in a trench coat.  

Refueled by high fashion and strong coffee, we rejoin the A1, and after an hour on the highway, peel off onto a country road and begin to climb the 1,985 ft hill on which Montepulciano perches. Its maze of honey-colored stone streets provided the setting for one of the Twilight films, while San Biagio church was featured in Under the Tuscan Sun , but wine is the star here. Every door seems to lead to a wine cellar, and its Nobile di Montepulciano is one of Italy’s oldest varieties, first documented in 789 CE. “Red wine in Tuscany is like an institution—50 years ago, nobody drank white wine here,” says Francesco Maramai, a sommelier who has served Hollywood stars and a former U.S. president at his family’s restaurant and wine cellar, Osteria del Borgo . ( Read more about wine tasting in our perfect pit stops, below .)  

Driving in Italy: Your need-to-know

Highways are toll roads

While some allow you to pay by card, some do not, so ensure you have a stash of cash at the ready. 

Observe the speed limits

You will be in the minority, but there are plenty of speed cameras that may catch you out. Speed limits will be in km/h: from 50 km/h (30 mph) on urban roads, up to 130km/h (80mph) on autostrade (highways). Look out for signs saying controllo elettronico della velocità (speed camera), and warnings to rallentare (slow down); rallentamenti means “delays.” 

Enter a ZTL at your peril

Rental cars don’t have the right to drive into any zona a traffico limitato (limited traffic zone), which you find in most city centers, including Florence and Siena. Fines will be issued if you’re caught. 

Pack your attitude

Italian drivers are assertive. They may drive close to you, sometimes beeping or flashing their lights before they pass. You may also want to consider taking out full insurance on your rental car; scratches and dings are a common sight. 

Seatbelts must be worn

That’s for the driver and all passengers. The law also requires there to be a reflective safety vest in the car, and (over winter) snow chains. 

Have your headlamps on at all times

Even in bright sunlight. It’s the law. 

Parking is color-coded  

A white outline means it’s free (but could be solely for residents; look for signs saying solo residenti or solo autorizzati ), yellow are reserved, and blue are paid. The safest option is to find a car park. Parking can often be paid via the EasyPark app; download it in advance to pay quickly and easily. 

Our drive the next day takes us into the Val d’Orcia, through velvety, luminous green valleys studded with poppies. To say it is breathtaking is to undersell it; each new vista of rolling hills and perfect avenue of cypress trees striking you dumb. The 15th-century Pope Pius II built his summer residence here, in the tiny town of Pienza , which was conceived as the ideal city; and after pausing in his serene garden, it is hard to disagree.  

The Mall Firenze has a clientele so chic, we even spot a baby in a trench coat

We pause for lunch in the wisteria-draped main square of Bagno Vignoni , which takes its name from one of the natural hot springs found across the region. Renaissance architects channeled the waters into a perfectly rectangular pool, but as our waitress tells us, you can’t swim in it; instead, she recommends heading further south to local favorite, Bagni di San Filippo ( see below ).   Tonight, we are staying in the tiny medieval village, Lucignano d’Asso, where the local bar has a docile visiting fox and excellent food, while our accommodation, Borgo Lucignanello Bandini , has a hilltop pool, and apartments with pretty bathrooms in grapevine tile and towels monogrammed with a cursive P. This, it transpires, is for its Sienese owner, Angelica Piccolomini, whose ancestors acquired the village in 1485, and whose family tree includes a certain Pius II. The hotel also arrange our next morning’s activity: a trip with a truffle hunter ( see below ).

Three perfect pit stops

Go truffle hunting (and eating!)

Spend an enormously fun morning with award-winning tartufaio (truffle-hunter) Paolo Valdambrini, whose three talented dogs help him scour the forests near San Giovanni d’Asso for one of Tuscany’s most valuable commodities. Mily, the oldest of his three dogs, a cream-colored, curly-haired lagotto romagnolo , an ancient breed prized for their super-sensitive noses, leads you by her nose through a forest, sniffing out treasure as she goes. Once, she found a 21-ounce specimen: “It didn’t fit in my pocket, so I put it in my hat and carried it home,” laughs Valdambrini. Afterwards, visit the Osteria delle Crete , where talented chef Donatella Varrunghi will whip up bruschetta and tagliolini, both topped with shavings of truffle. 

Soak in natural hot springs 

The steaming sulphuric waters of Bagni di San Filippo are a favorite of locals and visitors alike: Bring your water shoes and climb as high up as you safely dare—the higher you go, the hotter the water. While there are other hot springs across Tuscany, this one is notable for its size, and for the small natural pools—like bathtubs—scattered across it. Locals swear the white mud is good for your skin. Don’t forget to bring a big towel (or even a bathrobe) for the walk back to the car. There’s no entry fee, but you must pay for parking. 

Sample the local wines

There are countless vineyards in Tuscany, but if you’re driving, pick a tasting in a town so you don’t have to drive afterwards. In Montepulciano, sommelier Francesco Maramai demystifies Italian wine, showing you why you can ignore the striped paper ribbons often mistaken for a designation of quality. You will try prosecco, two Tuscan whites, three of its reds including a Brunello that’s “like a battleship,” and a divine 1996 vin santo (which we are advised not to dip cantucci into). Snacks keep you relatively sober on the way. All can be shipped worldwide.  Book here

The last leg of our journey takes in another storied stop: the medieval city of Siena , with its seashell-shaped Piazza del Campo. In July and August, the grand piazza hosts the annual Palios, raucous bareback horse races pitting the city’s ancient wards against each other. Today it is merely mobbed by tourists; after finding a spot in one of the bigger car parks outside the city walls, we happily join the throngs to soak up the history.

Back on the road, we join the SP222, also known as the Via Chiantigiana—named for the Chianti wine region through which it winds. As Maramai warned us at our wine tasting, you could drive from Siena to Florence in just over an hour; but the undulating, snaking switchbacks of SP222 are not about speed. This is a route lined with densely forested hills, ancient olive groves, and the neat stripes of vineyards—hence its other name, the “Strada del Vino.” It’s a route to be lingered over like a lazy lunch, where the landscape is as much to be celebrated as a glass of Chianti Classico. With a plate of tagliolini al tartufo , of course.  

Kate Bussmann

Kate Bussmann is an editor at Expedia Group, covering all aspects of culture and style. She has hosted live and online events, written and edited for titles including  The Times ,  The Telegraph ,  InStyle ,  Glamour , and  Marie Claire , and appeared on NPR, the BBC and Sky News. She has lived in London, New York and Naples, and one day plans to move to Paris. 

An Italian adventure

Take the wheel in Tuscany

The joy of a road trip is having the freedom to travel wherever the breeze may take you… with spectacular stop-offs planned along the way, of course. From car hire to castles, restaurants to hotel rooms, here’s our ultimate itinerary.

Pick up your car: Hertz Florence Airport

Via Palagio degli Spini, Florence 50145

Stay: The Artists’ Palace hotel

Piazza San Lorenzo 6, Florence 50123

Shop: The Mall Firenze

Via Europa 8, Leccio 50066

Stay: Delcorto Suites

Via di Gracciano nel Corso 28, Montepulciano 53045

Drive: Val d’Orcia

From Pienza to Montalcino via San Quirico d’Orcia

Experience: Hot springs

Bagni San Filippo

Stay/experience: Borgo Lucignanello Bandini and truffle hunting

Località Lucignano d’Asso, near Montalcino 53024

Drive: Via Chiantigiana

From Greve in Chianti to Gaiole in Chianti

Last stop: Florence

Scan the QR code or select one of the links below.

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Italy Travel Guide: The Ultimate 2-week Road Trip

Italy, the country of pasta & pizza, architecture & history, jaw-dropping sceneries, world-famous cities & medieval little towns, and mouth-watering gelato. That’s right – Italy has it all, and that’s why it is one of the most-traveled destinations in Europe . Multiple visits are needed to see all the country’s highlights. Discover the best of Italy within 2 weeks in this Italy Travel Guide.

Italy Travel Itinerary

All popular cities, like Venice and Rome , are well connected by train, car, or airplane. The best and fastest option is traveling by train, and the best way to see the country is by car, so this Italy travel itinerary is a mix of those.

Also have a look at our 7-day Italy itinerary !

Day 1-3: Rome

Start your trip in the capital of Italy: Rome . Rome has some of the world’s most popular tourist attractions; the Colosseum and Vatican City. Flights to Rome are usually the most affordable, which makes it a great start location.

Where to Stay in Rome

Rome offers accommodation for every kind of budget, including plenty of great hostels ( search all hostels in Rome here ).

Hotels in Rome 😴

Piazza Navona and San Lorenzo are central areas within walking distance of many of the top attractions. However, San Lorenzo is slightly cheaper if you’re traveling on a budget.

Day 4: Tuscany – Best of the Italy Travel Itinerary

Tuscany, with its rolling hills and vineyards, is one of the most picturesque regions in Italy. Escape the city, rent a car in Rome, Italy , and drive 3 hours along Lago Di Bolsena to Saturnia , the thermal area. Spend the afternoon and have dinner in this tiny medieval village called Montemarano.

We recommend to rent a car in Italy through Sunny Cars with free cancellation and insurance included. Book your rental car here .

Day 5: Tuscany ( Siena )

No better way to start your day than by dipping into the natural hot springs in Saturnia. Between 7-8 AM is the best time to visit, and if you stay at this hotel , it is just a 5-minute walk.

Here are all your hotel options in Saturnia.

Hop back into the car and continue your Italy travel itinerary for 3 hours along the most scenic roads toward Siena. Do note that your navigation has to be set to ‘Avoid Highways’. Siena is a beautiful old city with a UNESCO status.

Close off the day by having a delicious Italian dinner at Osteria Permalico . After that, spend the night in charming Siena ( this was our hotel ).

Where to Stay in Siena

If you’re only staying for one night in Siena, stick to the city center (around the Torre del Mangia), so you are close to all the historic landmarks, bars, and restaurants.

Hotels in Siena 😴

Alternatively, if you want to get back on the road early the next day, opt for rural accommodation within easy driving distance of the city.

Day 6: Tuscany (Siena to Florence)

On your last day in Tuscany, roam around Siena for a couple of hours, and visit Piazza Del Campo and the cathedral Duomo di Siena.

Siena’s old city center has a great ambiance. Cars are not allowed inside the old city center. Therefore, the city is a favorite on every Italy travel route. Read more information about where to park your car in our Tuscany Guide .

Read: The best things to do in Siena, Italy

Around noon, continue to your last stop: Florence . Optionally, visit San Gimignano or Volterra and drop off the car in Florence.

Day 7: Florence

Welcome to Florence. Spend the next 24 hours wandering around this ancient city and discover sites like the Duomo of Florence and the ancient bridge Ponte Vecchio.

While you’re in Florence, don’t miss out on a foodie adventure. Hop between cafes and restaurants, trying delicious fresh pasta and finding the best gelato!

Where to Stay in Florence

Florence has plenty of great accommodation options, from cute guesthouses and budget-friendly hostels ( search for your hostel here ) to luxury hotels.

Hotels in Florence 😴

Santa Croce is the best area to stay with loads of small bars and walking distance from all the things to do in Florence.

Day 8-10: Cinque Terre

In the morning, take the train from Florence to Cinque Terre , a 2.5h journey. Cinque Terre is a national park with five incredibly picturesque villages with hiking routes where you want to spend as much time as possible.

Spend two nights in Riomaggiore , Monterosso , or La Spezia, which is right outside the national park. ( Find the best train tickets here )

Read: Everything about Cinque Terre

Where to Stay in Cinque Terre

Accommodations inside Cinque Terre National Park are booked far in advance. Hotels are mostly available in Riomaggiore and Monterosso but expect to pay way over your typical budget per night.

Hotels in Cinque Terre 😴

A more affordable choice is to stay in La Spezia , where hotels start at 35 EUR a night. Alternatively, for the most budget-friendly option, search for a hostel in the area .

Day 11: Cinque Terre to Venice

It’s time to head to Venice , your final stop on your Italy travel itinerary. Take the train from La Spezia to Venice, a 5-hour ride with one transfer in between. The train is super convenient in Italy as some of the best you will see in Europe.

Find the best train tickets here

Day 12-14: Venice

Welcome to the city where everything goes by boats and bridges. Venice is one of the world’s most unique cities and an absolute must-see when you travel to Italy. Spend your last days in Italy strolling along the canals or crossing bridges sipping Italian coffee.

The mornings or late afternoon are the best times to stroll down the narrow streets of Venice as the city center gets busy during midday as the day trippers arrive in the city.

See the best things to do in Venice

Where to Stay in Venice

Stay in the middle of the city but tucked away in a quiet street 5 minutes walking from San Marco Square at Novecento Boutique Hotel .

Hotels in Venice 😴

If you’re on a tight budget, your best option is to stay outside of Venice on the mainland.

Costs of Traveling in Italy

The costs of traveling in Italy depend on where you eat, sleep, and how you get from A to B. These are the average expenses when you follow this Italy travel itinerary, eat at medium-priced restaurants, and travel by train + car.

Travel on a budget in Italy, from $570 − $630 USD weekly per person, mid-range $1220 − $2800 USD, and high-end from $2660 − $4090 USD. However, costs depend on factors like accommodation, transportation, and activities. We did not include flights. Check flight prices here

• Hotels: $65 − $300 USD Check available hotels
• Hostels: $20 − $40 USD Check available hostels
• Transport: $20 − $30 USD Book public transport
• Car Rental: $50 − $150 USD Book a rental car
• Food: $20 − $80 USD
• Activities: $20 − $45 USD See tickets & tours
• Sim: $1 − $3 USD Get an eSIM or SIM here
• Travel Insurance: $2 − $6 USD Get Travel Insurance

How to Get Around Italy?

Transportation plays an essential part in your Italian experience. Your Italy travel itinerary can be done by train, car, or plane. The fastest and most affordable way to travel in Italy is by train. However, a car gets you to those scenic country roads.

Renting a Car in Italy

For full flexibility and to go off the beaten path, driving a car is a perfect option. All major cities in Italy are well connected by train, but to visit Tuscany or the Dolomites, you need to rent a car. Avoid popular cities by car, as parking costs are sometimes the price of a train ticket.

Italy by Train

Traveling around Italy by train is excellent. They are incredibly fast (up to 350 km/h!), affordable, and much cleaner for the environment compared to an airplane. Book the train tickets a few days in advance to secure your spot on the train.

See tickets and availability for your train trip in Italy

Italy by Airplane

Just like the train, all major cities have international airports with domestic flights that connect cities internally as well as international flights.

However, the train might be a faster option for your trip around Italy, as the extra airport time adds up quickly.

Best Time to Visit Italy

Tourism in Italy is huge because it is one of the most-visited countries worldwide, so it is recommended to avoid the high season.

The best time to go to Italy is in spring, from April to June, and fall, from September and October. Prices are lower, fewer tourists, and comfortable temperatures.

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Looking for more travel information? Plan a chat with us for personalised travel advice or get an answer from the Salt in our Hair Travel Community on Facebook.

Hi, just wondering what you guys did with your rental car after Saturnia springs? Wondering if going back to Rome & returning it would be the best option to take the train to Florence. Definitely want to do Rome the first couple of days, Saturnia springs, as well as Elsa trail & Diborrato waterfall in Tuscany, then either Florence or Venice (would love if you could suggest one over the other) and definitely would like to stop in Cinque De Terre for a day or two. Just wondering if returning the car and going by train is best in that case. Any advice would be appreciated. Thank you!!

Hi Victoria, time-wise it’s better to rent a car for the part from Rome to Florence and carry on by train from Florence :-) However, it depends on how much the rental company charges you for returning the car at another city. If that’s way too much, you can drive back to Rome and take the train.

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This Travel Blog about Tuscany will help you discover this extraordinary region of central Italy, providing practical info and useful travel tips as to the best sights and destinations in Tuscany, the must see visits, the best areas to explore, the recipes of the tradition, and the best hotels, farmhouses, and apartments to stay in Tuscany. Whether you’re looking for a touch of culture, a sandy beach, an unforgettable landscape, or an adventure break, Tuscany may well be the holiday destination you’ve been looking for. Happy traveling!

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Tuscany ! One of the most beautiful, surprising and extraordinary regions of Italy , il Bel Paese! Centuries of history, sensational landscape, and incredible works of art, from the Etruscans and the Romans to the amazing Renaissance and the rise to power of the now famous dynasty of the Medici family .

Unique frescoes, paintings, buildings, sculptures and masterpieces of any kind, everywhere! Just think of the Gallery of Uffizi , the Leaning Tower of Pisa , the David by Michelangelo , Piazza del Campo in Siena and its Palio , the unique towers of San Gimignano .

Why Visit Tuscany in Italy?

The reasons to come and visit Tuscany are countless, here you can find everything you may desire: unique art, unique nature, unique food and fine wines, unique landscape, unique people. The main art cities in Tuscany , Florence , Siena, Pisa, Lucca, and Arezzo , are works of art in themselves and full of immense treasures to discover. The fantastic journey continues with an endless number of smaller medieval hilltop towns and villages that will leave your breath away! First of all the ancient town with many medieval towers: San Gimignano! Then Volterra, Pitigliano, Monteriggioni, Montepulciano, Pienza, Montalcino, Cortona … the most beautiful villages in Tuscany .

The natural territory of Tuscany is also extraordinary: scenic and breathless countryside with rolling hills, castles, hill villages, endless vineyards, beautiful mountains and paths, wonderful sea coast and islands. Chianti , Valdorcia , Monte Argentario , Crete Senesi , Val di Chiana, Costa degli Etruschi, Casentino are all areas of exceptional beauty and home of world-famous wines like the Chianti Classico , the Brunello of Montalcino , Bolgheri Sassicaia .

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I’m Elena , Tuscany born, mum and blogger living in the beautiful countryside near Florence , and I love this incredible region! My Tuscany Travel blog is for all who love Tuscany and want to know more about it: tasty Tuscan recipes , unique places to stay , art and traditions , beautiful hill towns , top destinations, and lesser known and hidden corners! 

I love to give free travel tips about Tuscany and Italy , and, as a local, I can help you planning your holiday in Tuscany (you can ask me here for a customized travel itinerary ) or simply help you realize traditional Tuscan recipes and suggest cooking courses of Italian and Tuscan Cuisine .

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Enjoy Tuscany!

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11 Best Hotels in Tuscany, From the Coast to the Outskirts of Florence

By Alex Erdekian

While Tuscany is hands-down one of the best places in Italy to visit, there's no getting around it—it's difficult to plan a trip there. The myriad of tiny towns you've never heard of, vineyards, hills, and networks of highways to cross en route to your destination are the region's entire charm, but also are what makes it so complicated to navigate. However, a great hotel (and accommodating concierge) can help smooth out the process—which is why we've rounded up Condé Nast Traveler's highest regarded Tuscany hotels. Read on for 11 of the best hotels in Tuscany.

Every hotel on this list has been selected independently by our editors and reviewed by a Condé Nast Traveler journalist who knows the destination and has visited that property. When choosing hotels, our editors consider properties across price points that offer an authentic and insider experience of a destination, keeping design, location, service, and sustainability credentials top of mind.

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

La Roqqa Arrow

The location: Porto Ercole, an area with built in exclusivity due to a hard to reach location on a quiet bay

Top amenities: Balconies or terraces in every room; everything from hiking and biking tours to horse riding or wine tasting tours can be arranged by the guest services team

It’s been eons since a new hotel graced Porto Ercole, a chic but discreet village on the Monte Argentario peninsula that’s home to Caravaggio’s tomb. The newcomer creating ripples on this part of the rock-strewn Maremma coastline is petite La Roqqa, a cliffside retreat whose distinctive coral-orange façade and secluded views of the Tyrrhenian Sea provide a forward-looking alternative to Hotel Il Pellicano, the area’s sine qua non grande dame since 1965. In the 55 rooms and suites, floor-to-ceiling windows let sunshine flood onto walls of sage green or Terra di Siena orange, which pop against crisp white bed linen. Designers Palomba Serafini, Milanese masters of uncluttered contemporary chic, have mixed midcentury pieces and Gaetano Pesce’s iconic Up chairs with ultramodern features, including an eye-catching white central staircase spiraling from the entrance. On the alfresco rooftop, Ferragamo-clad locals sip Negronis gilded by sunset rays in view of the 16th-century Forte Stella and harbor yachts below. Aperitivo hour turns into dinner at the outdoor Scirocco restaurant, where chef Francesco Ferretti knocks up fresh sea bass and other local seafood capped with Venetian grappa. Days spent lounging at the hotel’s smart Isolotto Beach Club are broken up by lunches of avocado and tuna salads paired with a local white. Or you can ask friendly staff to book you a Vespa tour along the rugged coast. It’s la dolce vita reimagined for the next generation. —Erin Florio

Hotel Il Pelicano Arrow

Porto Ercole

The location: Porto Ercole, a coastal town in Southern Tuscany situated around a yacht-filled harbor, halfway between Florence and Rome Top amenities: The beach club—one of Italy's best oceanfront properties, and a 2023 Michelin-starred restaurant

Il Pelicano is one of Italy's most legendary and best-known hotels, one which has been open since 1979 and where Sophia Loren and other Hollywood royalty have stayed. The bedrooms are crisp and bright: some have ocean views, some have balconies and terraces, and some have floors made of Carrera marble. The more casual restaurant, Pelligrill, is considered a classic with the yacht crowd and overlooks the pool and ocean, perfect for sunset; while the 2023 Michelin-starred Restaurant Il Pellicano earned accolades for its creative uses of ingredients from land and sea including pigeon, lobster, and shrimp.

Casa Iris Arrow

The location: Orbetello, a small, walled coastal town on a lagoon and a peninsula, Grosseto, once the site of an ancient Etruscan settlement; located midway between Florence and Rome

Top amenities: Breakfast served, highly personal service from the two owners

This luxurious, all-done-up bed and breakfast, set in a peach colored palazzo on the town's main drag, is highly personal, with just three bedrooms inside and the owners filling the roles of concierges. Before they purchased it, the 15th century property was full of historic frescoes—the owners proceeded to hire a restorer who had worked on the Sistine Chapel to make it their own. A cozy breakfast is served to guests in the communal kitchen, featuring fresh apricot jam; and the rooms are works of art, with walls whose historic layers of paint have been scraped into designs.

Rosewood Castiglion del Bosco Arrow

The location: Montalcino, a hilltop town famed for its production of Brunello di Montalcino wine, made from the town's sangiovese grosso grapes—it's an hour and a half by car from Florence and 45 minutes by car from Siena

Top amenities: On-site Brunello di Montalcino winery, 18-hole golf course, cooking classes, spa, infinity pool, truffle-hunting outings

We've already listed the terrific amenities—which, yes, include truffle hunting—but if you need more information on Rosewood Castiglion del Bosco, we'll go on. This Tuscan estate is on 5,000 acres and has 42 suites and 11 villas. Travel reporter and Condé Nast Traveler contributor Laura Itzkowitz —who lived in Rome previously and writes often about Italy—describes the bedrooms as “lavish” in her hotel review for the magazine:

“If money were no object,” she writes, “I would check into one of the sumptuous villas and never leave. Each one comes with a private heated pool, though some feature woodburning pizza ovens, a home theater, or tennis court.”

Jamie Spain

Kelsey Glennon

Megan duBois

Boone Ashworth

Castello di Vicarello Arrow

Poggi del Sasso

The location: A true village in central Italy with a population of 88

Top amenities: Vegetable garden with ingredients used in food on-site, yoga, alfresco spa

This nine-suite retreat, formerly an actual family home, is set within a 12th century medieval castle. But in spite of the down-home, rustic setting—there are no TVs—this place is totally chic. Mario Testino shot a Vogue photo shoot here featuring Lara Stone. The food is an offering that sets Castello di Vicarello apart from the others in the Tuscany hotel landscape. Here's how contributor Sophie Goodwin describes it in her first-person Condé Nast Traveler hotel review: “Ingredients are fresh from the vegetable garden, eggs straight from the chicken coop, and cakes and bread baked every morning. Breakfast is slices of Pecorino with bread, eggs with sunny orange yolks, and strong Italian coffee. Wild boar is breaded and served with a dollop of olive-oily-aioli, the al-dente spaghetti comes with fresh tomato.”

We don't need any more convincing.

Renaissance Tuscany Il Ciocco Resort & Spa Arrow

The location: Outside the walled medieval city of Lucca, an all-time classic day trip from Florence

Top amenities: Spa, pool, bar, 24-hour service

The Renaissance Tuscany Il Ciocco Resort & Spa, a 180-room luxury resort hotel by Marriott International, is surrounded by 1,500 acres of green hills and land—and by all of the special perks, amenities, and experiences you would expect from the brand. These include marble bathrooms in the rooms, cooking classes from the restaurant, and destination weddings packages. The ideal location in the heart of Tuscany means exploring the region's vineyards, tasting wine, and biking, hiking, and horseback riding are all activities on demand—not to mention the ability to stroll through the historic towns of Lucca and Barga.

Fontelunga Hotel & Villas Arrow

The location: The city of Arezzo, in eastern Tuscany, is well-known among history buffs and wine enthusiasts alike, and is home to a famed 15th century fresco of Mary Magdalene, as well as ample Chianti wine vineyards

Top amenities: Complimentary breakfast and bicycles, pool bar, on-site dinner parties, private cooking lessons at an extra cost

Italy writer Bridget Arsenault kicks off her hotel review of Villa Fontelunga in the dreamiest way possible:

“Set amid 200 olive trees,” she writes, “Villa Fontelunga's marmalade-colored building appears against the blue sky as you enter the driveway. Set within the beautiful hilltop town of Cortona, the hotel offers spectacular views across the Val di Chiana in the heart of Tuscany. An intimate, fairly remote Tuscan getaway, this hotel takes some research to track down. Once there, you'll find everyone from honeymooners to Italian adventure-seekers inspired by Under The Tuscan Sun to retired couples enjoying la dolce vita.” If that isn't inspiring enough, the details she reports—including the two tiny dogs who run around the property, the Tuesday and Thursday chef-hosted dinner parties, and the honesty bar by the pool—really seal the deal.

Relais Sant'Elena Arrow

The location: Bibbona, situated between beach and forest, and home to a centuries-old fortress and medieval piazzas Top amenities: Complimentary breakfast with an Instagrammable spread, guided farm tour with olive oil tasting, cooking class, holistic spa

This dreamy farmhouse-style 16-room boutique hotel emulates the Tuscan experience to a tee. Guests enter a secluded tangle of ivy, rose gardens, stone walls, and wood beams, the stuff of Italian storybooks. The rooms and the dining program alike are top-tier. Bedrooms are full of antiques and rain showers, while the food offered includes fresh ingredients from the on-site garden and olive oil made on-property. The food was the favorite part for reviewer, Bridget Arsenault again, who also highly recommends the bookable cooking class:

“There's daily lunch (poolside or in the whimsical garden) and you can order drinks throughout the day,” she writes. “Dinner is an otherworldly affair. You can also book an on-site cooking class and learn to make Tuscan classics like ribollita and pappa al pomodoro, fresh pastas with ragu, and tiramisu.”

She also reports a romantic vibe, and says that you'll find plenty of honeymooners and couples here.

Cala del Porto Arrow

The location: Harbor-side, in a small town on Tuscany's Southern coast

Top amenities: Sister property Cala Beach located directly on the beach, hands-on winemaking opportunity, bookable experiences including cycling tours in the Maremma and day trips to the archipelago's island

It's hard to go wrong when you're staying on a serene archipelago surrounded by turquoise harbors, smack between land and sea—the glittering ocean and Tuscan wine country. At Cala del Porto, guests get the best of both worlds. But the resort itself takes the joys even further with five-star service, in-room balconies, four restaurants, and planned experiences and excursions that are made accessible, including private yacht tours, golfing and wellness packages, and biking and wine tasting tours.

Hotel Adler Thermae Arrow

Bagno Vignoni

The location: Bagno Vignoni, a hamlet in the province of Siena well-known for its dramatic hot springs, overlooking Val d'Orcia, a UNESCO World Heritage Site since 2004

Top amenities: Thermal swimming pools, sauna, steam bath, holistic spa

One of the most unique places to stay on this list, Hotel Adler Thermae makes use of its location on Tuscany's hot springs in the most delicious way possible—by providing a compound of thermal swimming pools, baths, and spas full of travertine grottoes, stalactites, and stalagmites, for guests to luxuriate in. Staying somewhere like this is one of those wish list travel experiences most people only dream about. The resort has plenty of other things going for it too, though: a glass-roofed restaurant, stellar wine list, and in-room terraces, to name a few.

Castel Monastero Arrow

Castelnuovo Berardenga

The location: Castelnuovo Berardenga, a village that's a day trip from Florence, full of castles and Romanesque churches Top amenities: Interlocking swimming pools

Castel Monastero, a castle of a hotel 15 miles from Siena with 75 guest rooms, is well-situated for the quintessential Tuscany trip. The spacious accommodations here have “wood beams, comfortable leather sofas, terra-cotta floors, and views into the valley,” according Traveler 's review of the hotel. The interlocking swimming pools have those picture-perfect valley views, as well. Oh, and how could we forget? There's also a 13th century wine cellar on the property.

For more inspiration, see our first-hand researched rankings of Italy's best hotels, Airbnbs, and villas.

Editor picks:

• Our Ultimate Italy Where-to-Stay Guide
• Best Hotels in Florence
• Best Hotels in Rome
• Best Hotels in Venice
• Best Airbnbs in Italy
• Best Airbnbs in Rome
• Best Airbnbs in Venice
• Best Villas in Italy
• Best Villas in Tuscany
• Best Villas in Lake Como

2023 Readers' Choice Awards picks:

• Best Hotels in Italy, According to Readers
• Best Hotels in Florence, According to Readers
• Best Hotels in Rome, According to Readers
• Best Hotels in Venice, According to Readers

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13 Perfect Looks to Pack if You’re Going to Tuscany or Want to Emulate Italian Summer Style — From $10

Starting with a breezy sundress and comfortable walking sneakers.

As a travel editor who’s been to more than 40 countries, I’ve seen a lot of the world — but I still haven’t found anywhere that compares to Italy in the summer . My sun-kissed memories of cruising around Capri, leather-shopping in Florence, and bike riding through Chianti vineyards are some of my fondest, which is why I can’t wait to get back there in May. This time I’ll be focusing on Tuscany, and you can bet that I plan to live out my dreams of lounging by the villa pool with a spritz in hand.

Of course, I’m going to need a wardrobe that lives up to the glam of this trip (but that fits in a carry-on since I haven’t checked a bag in four-plus years , and I’m not about to start now). With past Italy visits under my belt, I already know I’ll need comfortable walking shoes and a breezy sundress , but I’m adding a few new looks to my suitcase, including wide-leg pants and a matching set . Here’s what I’m eyeing for my trip to Italy — and hopefully, it’ll inspire all of your out-of-office adventures near and far, too.

The Perfect Sundress

I can see it now: I’m walking through Florence with a gelato and admiring the Duomo, wearing the perfect sundress. For this, I’ve already picked up the Melody Smocked Midi Dress from Madewell in black knowing it’ll take me from day to night — city walk to aperitivo — effortlessly. Thanks to its ultra-flattering fit with a smocked top and gentle A-line flare, I wouldn’t doubt if you see this midi dress way beyond Italy this summer. I’m going to pair it with white sneakers during the day and my platform sandals in the evening. I’m also eyeing this beautiful white sundress and this aptly named “Tagliatelle” dress from Reformation .

Comfortable White Sneakers

I’ve been a loyal fan of the celeb-loved Veja Campo sneakers for years now, but after reading rave reviews of these cushioned, platform Dr. Scholl’s Time Off Sneakers , I may just make the upgrade before my trip. Even Oprah loves this brand , with shoppers saying they feel like “walking on clouds.” Sounds like they’re worth it, especially since they’re on sale. I plan to wear these with everything from my breezy sundresses to casual shorts. 

Leather Crossbody Bag

Lo & Sons

It’s practically shameful to walk through Florence’s leather market without your own nice leather bag, and this one from Lo & Sons recently changed my world . The stylish, versatile Lo & Sons Waverley 2 4-in-1 Bag has a convertible strap that makes it four bags in one. I can wear it on my shoulder, crossbody for more security, as a belt bag to keep my hands free, and as a wristlet for a night out. That covers pretty much everything on my itinerary — and cuts down on packing space.

Tailored Shorts

These high-waisted shorts are so classy and elegant, they practically scream “Italy vacation.” French-girl-favorite and T+L editor-loved brand Sézane must’ve thought so too because they named this style “Rome.” I love the elevated, tailored details like pleating and cuffs. For the same look for less, I’d spring for these casual $26 linen shorts or classic $25 white shorts from Amazon.

Oversized White Button-down Shirt

I’m convinced there’s no trip I can’t use this Hotouch oversized white button-down shirt for, which is why it’s a permanent part of my travel capsule wardrobe . I can use it to cover up in the morning or evening if it’s chilly or if I enter a church, or I can throw it on over a bathing suit by the villa pool in Tuscany. (Psst, you can shop more of our favorite oversized button-downs here!)

Maybe it’s the White Lotus Tanya McQuoid in me, but I can’t imagine my Italy trip without a silk scarf to tie around my neck or hair (while riding a Vespa, probably). I’m eyeing this pretty, neutral one from Fonyve from Amazon since it’s a steal at $10. I was sold the moment I read this five-star review from a fellow traveler: “Elegant, well-made scarf…The colors of these are very vibrant and look like expensive scarves from Italy.” 

I always had a lot of trouble finding sunglasses that fit my narrow face (I used to buy kids’ sizes!) — until I tried these frames at Warby Parker, the same affordable brand that makes my eyeglasses. I love that they have narrow, medium, and wide sizes to fit pretty much any face, and you can add polarization and your prescription to them, all for way less than you’d normally pay for name-brand sunglasses. There’s far less guilt than if I lost my Ray-Bans, but they’re still nicer than super cheap ones. If you’re still not ready to shell out $95 for a quality pair, you can’t go wrong with these Sojos vintage sunglasses at Amazon, which look just like them but are only $15. 

Wide-leg White Linen Pants

I’ve written before about how Madewell’s Harlow wide-leg pants are the comfiest pants I own and go with absolutely everything (I even purchased another color after originally buying them), but I’ll sing their praises again and again. They are made from a luxuriously soft lyocell-linen blend that keeps things cool even on hot days, and I’ve found they wrinkle far less than my 100 percent linen pants.

Thin Leather Belt

Sometimes crafting the perfect travel outfit is all about accessories, and the right belt can take a good outfit from good to bellissima. This thin, understated option from Jasgood adds just the right amount of polish to a look whether it’s cinching a billowy dress or adding the cherry on top of the perfect pants. Adding a belt is also great for switching up looks from day to day.

Cardigan Sweater

Nights can get chilly in the Tuscan hills — even June and July see lows of 60 degrees Fahrenheit. That’s why I pack a versatile cardigan that pairs with all my looks in case I get cold. To pass my Italy packing list test, I usually ask myself, “Would Audrey Hepburn have worn this?” And this one from J. Crew passed the test . There’s something decidedly European about its classic stripes, and its neutral palette will match with anything I pack. While the 100 percent cotton sweater is on sale for less than $100 (and has an impressive 4.7 rating), I found a more affordable lookalike at Amazon for just $40.

Matching Set

Matching sets are the epitome of no-fuss, one-and-done outfits that look put-together for any event on the itinerary, whether you’re sipping Chianti at a vineyard or exploring town. Plus, you can mix and match them with other shorts and tops in your suitcase for maximum outfit potential. I splurged on the Noah Two-piece Set from Reformation (look how perfect that “linguini” print is for an Italian wedding weekend event!) but I also have and would recommend something very similar to this $33 matching set from Amazon.

Wide-brim Packable Sun Hat

I plan to soak up the Tuscan sun on this trip and to make sure I’m protected and looking stylish, I’ll pack my trusty J.Crew Packable Sun Hat that’s taken me from Egypt to Greece and back. It easily folds right up into my carry-on, and only takes minimal zhuzhing to get back to its original shape. I’d snap one up while they’re still 62 percent off if I were you.

High-waist Yoga Shorts

One of the most magical moments of my last trips to Tuscany was a bike ride through Chianti. I’m planning to convince my travel partners to re-create that, and I know for that I’ll need some athletic shorts like this pair I swear by from The Gym People. They’re perfect when strolling through markets paired with my oversized white button-down, sun hat, and sneakers. 

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How to taste your way through Tuscany

Italy is known for its vibrant and varied cuisine. Discover it at its best in the region of Tuscany, where an assortment of inviting culinary experiences offer a true taste of the country.

Located in west-central Italy, the region of Tuscany is rich in natural beauty. Its striking landscapes vary from the chiselled Tuscan-Emilian Apennines in the north and the rugged Apuan Alps in the north-west, to the gentle green hills of Val d’Orcia in the south.

The region’s capital, Florence, is a destination renowned for its art and architecture. Its most iconic sight is the eminent Duomo, a stunning 400ft-tall masterpiece of the Renaissance. During its 100-year build, architect Filippo Brunelleschi is said to have introduced a pulley system to speed up lunch breaks, feeding the workers on the cathedral’s roof with peposo , a black pepper and beef stew.

Today, food remains an important part of Tuscany’s culture, and visitors are encouraged to slow down and savour the wide variety of culinary experiences on offer across the region — from truffle hunting and cheese tasting to sampling fine wine and sipping fresh coffee — here's how to get a taste.

1. Join a truffle hunt

Truffles are deeply rooted in Tuscan history, found throughout the region in all shapes and sizes and revered for their distinctive aromas and flavours. Learn about the timeworn traditions and distinct hunting practices of those seeking these subterranean delicacies at Italy’s first museum dedicated to truffles — the Museo del Tartufo e Centro di Documentazione — housed in an old castle in San Giovanni d’Asso. At Cucina Giuseppina , near the town of Certaldo, forage for your own truffles with the help of a guide and trained truffle-hunting dogs, before indulging in a truffle-based Tuscan lunch. In summer, you'll search for the elusive black truffle, while in the fall, the white truffle is the prize.

2. Try tasty cheeses

Tuscany is best known for pecorino, a sheep’s milk cheese — and especially treasured by Tuscans is the bold-flavoured pecorino cheese produced in Pienza, the aptly named pecorino di Pienza . Elsewhere in the region, the exuberant Palio dei Caci event draws crowds to the town of Volterra each October, where ‘runners’ compete to skilfully guide wheels of pecorino down a cobbled street. Many working farms in Tuscany are open to visitors, too, so you can learn how the cheese is made. Fattoria Corzano e Paterno just south-west of Florence produces cheese, wine and olive oil and also has guesthouses, a farm shop and a restaurant, with tasting sessions available year-round.

3. Make pasta from scratch

Handrolled pici is a popular pasta in Tuscany, often served with tomato, garlic and breadcrumbs. Pappardelle pasta is also a local favourite, generally served with rich and meaty sauces. Join a class to learn how to make your own pasta at wineries such as Magida in Brunello, which also offers accommodation packages. Private cooking lessons are also an option, where you can learn the art of the perfect pasta dish from professional chefs such as Antonella La Macchia .

4. Sample a variety of wines

Tuscany is well known for its geographically protected wines such as Chianti, Montepulciano and Brunello. Stop by the Enoteca la Fortezza wine bar inside the Fortezza di Montalcino and sample Montalcino's intense and complex Brunello wines. Enjoy tart and spicy Chianti wines at Pietraserena Azienda Agricola Arrigoni in San Gimignano, as you admire the impressive views across the hills and vineyards. Although Tuscany’s established viticulture scene is revered, there are also a growing number of organic, natural and biodynamic wines being developed, helping the region stay at the forefront of Italian wine production. Antinori nel Chianti Classico has been making wine since 1385 and now has an ultra-modern winery attached, which is open to visitors. Or find one of the unique buchette del vino (wine holes) hidden around Florence — at restaurants such as Babae , Belle Donne and Il Latini , to name a few — where wine is served through a tiny window, a tradition that dates back to 1559.

5. Experience a traditional trattoria

With charming hilltop towns seemingly around every bend, it’s easy to fall in love with a new local trattoria every evening in Tuscany. On the edge of Panzano-in-Chianti, head to the terrace at Il Vescovino to enjoy homemade ravioli stuffed with leeks and taleggio cheese, served in a simple tomato sauce. Along Tuscany’s western coastline, restaurants such as Il Romito in Livorno serve up a homely fish stew called cacciucco — a 500-year-old dish traditionally made using five or more types of fish in a red wine and tomato broth.

6. Sip freshly roasted coffee

Italy has an affinity for coffee and on almost every corner in Florence you’ll find coffee ‘bars’ in which you can quietly perch to people watch. The city is also home to the Accademia del Caffè Espresso , which features a coffee museum and an indoor coffee plantation, and also offers a selection of educational tasting sessions. Away from the city, learn more about Tuscan artisanal coffee and the finer details of the roasting and blending processes with a tour of Pienza Coffee in Val d’Orcia.

7. Peruse local markets

Intense and aromatic, Tuscany’s local food markets are sure to delight — piled high with humble but delicious ingredients, from bread and cheese to tomatoes and beans. While some markets such as Florence’s Mercato Centrale are open daily, smaller towns in the region host their weekly markets on varying days. In the city of Lucca, head to the MercoledìBio on Wednesdays — for organic fruit and vegetables, honey, olive oil, cold cuts, wine, bread and baked goods, as well as sheep’s, cow’s and goat’s cheese — or the Campagna Amica market on Thursdays — for fresh fish and seasonal vegetables, cheese, plants and flowers.

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More From Forbes

Dolomites to tuscany: top places to stay in italy this summer.

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Whether it is the outstanding Renaissance monuments or authentic, regional cuisine, Italy’s appeal has long been far-reaching. As a country, it has never had to ‘hard sell’ itself to tourists, with the country being a perennial favourite destination for travellers. As well as having more UNESCO World Heritage sites than any other country (59 in total), its rich culture, architecture, art and beloved gastronomy is a source of inspiration for tourists across the world.

This year, Italy’s hotel world is upping the ante when it comes to its many standout luxury offerings, with a plethora of new openings and property updates giving even more choice to visitors. From Italy’s mountainous peaks to its azure waters in the dramatic south of the country, here is the latest hotel news.

The Dolomites

Known for its discreet hideaways in the Greek islands, the Casa Cook brand is opening its first Italian property at the end of this year. Located in Madonna di Campiglio in the Dolomites, in Italy’s Tentino-Alto Adige region, guests can expect a boutique offering that will channel the charm of the Italian Alps.

“Drawing inspiration from the art of slow-living and the elegance of modern-luxe minimalism, Casa Cook epitomises laid-back luxury for today's discerning travellers,” says Claire Camplisson, managing director of Casa Collective. “Each Casa Cook property offers an oasis to restore balance to the body and soul, rejuvenate the mind, and inspire new adventures.”

With a focus on architecture, local culture, community and health and wellbeing, the new Casa Cook will offer locally sourced cuisine, wellness facilities and excursions in nature.

The spa at Sensoria Dolomites.

Also found in the Dolomites, but this time in Italy’s South Tyrol region, is Sensoria Dolomites , an adults-only wellness retreat. New for this summer, the property is set to launch its new Sound Healing Retreats (9-16 June 2024), in partnership with Soundwave Gongs. The sessions will combine powerful vibrations of handcrafted German gongs, along with acoustics and percussions, to offer transformative experiences. Located at the foot of the Alpe di Siusi, with panoramic mountain views, modern interiors and South Tyrolean cuisine, the hotel also offers a collection of immersive experiences in local nature.

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Found in the rose-bowered vineyards of Franciacorta and the alpine foothills between the Po Valley and the southern shore of Lake Iseo, is L’Albereta . Following extensive renovations, the charming hotel has recently reopened its revamped Chenot Espace spa, the only medical and wellness spa signed by Chenot in Italy.

Found in Franciacorta, L'Albereta has revamped its spa.

As well as a highly qualified team of over 30 professionals, including doctors, therapists, dietitians, osteopaths and beauticians, Chenot Espace has introduced several new diagnostic treatment options to further enrich the wellness programmes. The new look of the 2,000sqm space includes the restoration of the first two floors of the spa and the Chenot restaurant using sustainable and natural materials.

THE ITALIAN LAKES

Found in the hills surrounding Lake Garda, and situated on the edge of a nature reserve, the recently opened Borgo Tre is carved out of a newly renovated 18 th -century farmhouse. The rural sanctuary offers just six luxury apartment-style suites, complete with their own private garden or terrace.

Borgo Tre is a new opening by Lake Garda.

The farmhouse retreat has a heated outdoor pool made from local granite, a spa inspired by the surrounding nature, with a relaxation area, yoga terrace, outdoor cabanas, cold tub and a Finnish sauna. Upcoming for this year are yoga retreats with classes to be held in the grounds.

Lake Como's grand dame hotel that is Grand Hotel Villa Serbelloni.

Meanwhile, one of Lake Como’s grand dames, the family-owned Grand Hotel Villa Serbelloni , has renovated its spa. The hotel has been welcoming in A-listers for 150 years and is found in the pretty village of Bellagio. The modern, streamlined wellness facility is a thoughtful contrast to the ornate interiors of the palazzo—think: grand marble staircases and giant chandeliers.

Passalacqua unveils its new spa.

Voted the best hotel in the world at last year’s The World’s 50 Best Hotels , Passalacqua has unveiled a brand new, atmospheric spa. Carved out of the hotel’s 18 th -century tunnels as well as an ancient greenhouse, the spa is a collaboration with Seed to Skin Tuscany—a natural skincare line that is inspired by curative traditions dating back to 1129.

Passalacqua's Sala Ovale.

Starting from the basement of the palazzo and reaching the shore of the lake, the tunnels connect to each of the hotel’s terraced gardens. A brand-new 18-metre indoor pool and whirlpool is located inside the antique greenhouse. The pool is lined with a precious mosaic of Palladian marble, where each individual stone has been cut and laid by artisans, creating a constellation of green, grey and blue shades. The view overlooks the Italian garden—a masterpiece by internationally renowned botanist, Emilio Trabella.

One for the watch-list is the upcoming Venetian property by luxury brand Airelles . The hotel, Airelles Venise, is set to open in 2025 and will mark the brand’s first property outside of France.

The top floor suite at Londra Palace has views across Venice.)

Londra Palace Venezia , a historic 52-room palazzo that originally opened in 1853, has recently completed an extensive renovation. Famous for its iconic 100-window façade, that overlooks the San Marco Basin in Venice, the hotel now features a contemporary aesthetic that honors the building's architectural legacy. Also on offer are immersive dining experiences and access to off-site visits to local artisanal studios through the hotel brand’s Place of Wonders Foundation. The hotel will also introduce ‘Mano a Mano’ (or ‘Hand to Hand’)—a collection of five objects created by five storied Venetian craftsmen. Each of the five limited-edition pieces will be on display throughout the property.

The Tosca restaurant at Castello di Casole.

This year, Tuscany is buzzing with new luxury offerings. First up is Castello di Casole, A Belmond Hotel , which has reopened for the season with a newly revamped restaurant concept, Tosca. Remaining at the heart of Castello di Casole, the restaurant has reopened with a fine dining direction and three new tasting menus, celebrating the best of the region. Headed up by executive chef Daniele Sera and chef Michele Raggi, who have worked together for the past 17 years, the menus celebrate the produce from the ‘Orti del Castello’, the hotel’s two vegetable gardens extending over one hectare of the 100% organic certified land.

Castello di Casole, a Belmond Hotel, is a gateway to Tuscany.

A former 10 th -century castle, Castello di Casole, A Belmond Hotel, Tuscany, retains the ambience of a private country house, with just 39 suites. It is a gateway to Tuscany’s rolling hills, olive groves, and vineyards—as well as to the Tuscan towns of Siena, Florence and San Gimignano. The property’s identity is deeply rooted in its agricultural past, stretching back to 7th century BC, with Etruscan artefacts found across the 3,200 acres of land.

Castelfalfi, a hilltop estate.

Meanwhile, Castelfalfi , a restored hamlet in the heart of Tuscany, has opened a new RAKxa Wellness Spa, stretching across 1,500sqm, with treatment rooms, saunas, a steam room, relaxation area, salon and granite-lined indoor/outdoor heated infinity pool. The sprawling estate ecncompasses one of Tuscany’s most scenic hill-top villages, and offers a contemporary-luxe hotel and stylish, renovated villas set in over 2,700 acres of ountryside, woodland, vineyards and olive groves. With a medieval-meets-modernity approach, Castelfalfi offers contemporary design, culinary creativity and transformational wellbeing.

Discover an authentic Tuscan experience at Borgo San Vincenzo.

Borgo San Vincenzo , on the other hand, is Tuscany’s newest luxury boutique hotel. Located amid the Vino Nobile vineyards of Montepulciano, the property is a reimagined 18 th century borgo (or village), offering curated experiences such as vineyard picnics, tours of local farms and pasta mills, Vespa experiences and voyages in hot air balloons. New for this season, the hotel has launched a Linger Longer offer which sees a 20% discount on stays of 7+ nights.

The new opening, La Serena, Forte dei Marmi.

Having just opened its doors in April 2024, La Serena, Forte dei Marmi is found on Tuscany’s Riviera, the glamourous beach destination for Italians looking to escape the northern cities during the warmer months. The property brings a fresh approach to the local hospitality offering with contemporary design throughout, and 30 rooms and suites, a restaurant, wine cellar, swimming pool, terrace and gardens.

The iris garden at Villa La Massa.

Meanwhile, celebrating the floral emblem of Florence and Tuscany, this month Villa La Massa , in Chianti, has announced the return of its ‘Iris Month’. In honour of the delicate Tuscan Iris, which blooms throughout May and June, guests are able to take part in new iris-themed experiences ranging from private dining or picnics in the hotel’s iris garden, iris-infused spa treatments, al fresco painting classes and flower arranging. The hotel can also arrange visits to one of Florence’s best kept secrets Giardino dell'Iris . Open for a limited period each year, this ‘Iris Garden’ is a beautiful oasis with over 1,500 varieties of iris and panoramic views of the city.

The terrace at The Place Firenze overlooks the centre of Florence.

Found in Florence, The Place Firenze is a celebrated hotel overlooking the Piazza Santa Maria Novella. Initially launched in 2003, the hotel has just reopened following an extensive renovation by award-winning design firm, Luigi Fragola Architects. The reimagined property encompasses 20 rooms and suites and a variety of common areas that will immerse guests in the local Florentine community.

Castello di Vicarello has opened its 10th suite.

Finally, Castello di Vicarello , a family-owned, 12th century castle hotel, has unveiled its latest accommodation offering—Suite Mezzatorre—adding a brand-new level of contemporary luxury to the former family home. Spanning 1,184 square feet, the new tenth suite occupies the entire second floor of the castle’s tower and boasts 360-degree panoramic views across the 100-acre estate. Each suite at Castello di Vicarello has been sensitively and uniquely restored, and the new suite follows this ethos with Italian and Indonesian antiques, a custom-made, free-standing copper bathtub and yellow Sienese marble shower—one of the rarest marbles mined in Italy. While design lighting, medieval arched windows and French oak parquet add to the homely feel, guests of Suite Mezzatorre will find a large private living room decorated with oriental rugs and featuring a cosy fireplace.

Out tomorrow with Forbes is Part 2 of The Best Places To Stay In Italy This Summer, From Umbria to Sardinia.

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