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Explore Portland with a REAL local!

Portland, maine's #1 city & lighthouses historical tour.

Welcome to The Real Portland Tour!

Hop aboard for a fun and authentic Historical Sightseeing Tour of Portland, Maine and 3 lighthouses with a guide who is a REAL local, born and raised right here in Portland! Let me take you for an insider’s look at the rich history and current happenings of this charming and highly acclaimed city. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a REAL local knows! 

The Real Portland Tour is the only tour of Portland that includes a full city historical tour and a trip to 3 lighthouses! I've been a tour guide since 2001, and I'm also a college librarian. I've spent years researching the hidden history of Portland, and I take pride in being the most informative, entertaining, and experienced guide in town! 

The Real Portland Tour has been featured in American Libraries magazine, named the #1 Thing to Do in Portland, Maine by The Abundant Traveler , and is the top rated City & Lighthouses Tour of Portland on TripAdvisor and Viator!

"Been to Portland 100 times...never knew most of the info shared. This guy needs his own tv show."

The real portland tour named the #1 thing to do in portland, me by the abundant traveler.

Check out the video !

The Real Portland Tour is featured in American Libraries magazine!

Read "The Man with a Van" here !

The Real Portland Tour Portland, Maine Spoken Word Poem/Rap recently published!

I'm honored to say my Real Portland Tour spoken word poem/rap about Portland, Maine history was published in the Longfellow Days Anthology titled "Read To Me Some Poem" 

Over 99% 5-Star Reviews on TripAdvisor & Viator!

The real deal..

I've been giving tours of my hometown of Portland, Maine for over 20 years, and in the offseason I'm a librarian at Southern Maine Community College. I have a Master's degree in Library Science, and I'm always digging into Portland’s history to find something new and interesting, while at the same time keeping on top of current happenings and making sure to visit as many local establishments (especially our world class restaurants and bars) that I can. I take pride in representing this city, and providing an authentic tour delivered with a true Mainer's sense of humor! 

In addition to being a tour guide, I am a featured poet for the annual Longfellow Days festival where I perform my Portland history spoken word poem/rap (you'll hear some of my rap on the tour)!

I've given more than 10,000 tours over the years to hundreds of thousands of people from across the country and the world. It has been an absolute honor to tell so many people the unique history of my hometown! I'm thankful every day to be able to do what I love to do. I hope to see you soon!

 *Tour length is approximately 1 hour and 45 minutes. Most tours sell out in advance, so make sure to book ahead of time directly on my website.

"Derek was a wealth of knowledge! So much personality! A driving/talking teaching/rapping librarian"

Important booking notice.

  *I strongly recommend booking directly on my website. Booking directly on my website brings you to FareHarbor, which is my preferred booking processor. Bookings processed via FareHarbor have full refunds for cancellations made up to 24 hours before your tour time.

If you decide to book on a different 3rd party site such as TripAdvisor, Viator, Groupon, etc, you are subject to their terms, conditions, and refund policies which may differ from FareHarbor.

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Copyright © 2024 The Real Portland Tour - All Rights Reserved.                                                              

96 Commercial St, Portland, ME 207-329-7401

PORTLAND EXPLORER

History, cultural, waterfront & lighthouse tours, portland, maine, portland explorer was voted tripadvisor’s travelers’ choice best of the best 2024.

This award is based on high levels of above-and-beyond traveler reviews in the last year — fewer than 1% of 8 million experiences are awarded!

OUR FEATURED TOURS!

• Most Popular
• Tags All Ages
• Hour Glass 2.5-3 Hours
• Up to 11 People

PORTLAND, MAINE CITY/CULTURAL/HISTORICAL & 3 LIGHTHOUSES TOUR

• Tags Ages 21+

LIGHTHOUSE TO LAGERS TOUR WITH CRAFT BEER AND LOBSTER ROLLS

Experience the best of coastal Portland, ME with our Lighthouses to Lagers tour! Explore Bug Light and Portland Head Light, then enjoy local brews at Portland Beer Hub. Join us for history, scenery, and craft beer – the ultimate seaside adventure!

• Hour Glass 1.5-2 Hours
• Up to 10 People

ECHOES OF THE WABANAKI: A CULTURAL WATERFRONT JOURNEY

Join us to gain a unique perspective on the cultural tapestry of Maine through the eyes of its original stewards, and leave with a deeper appreciation for the Wabanaki’s significant contributions to the region’s history and culture.

EXPLORE PORTLAND, MAINE’S SCENIC LANDMARKS ON A UNIQUE & INSPIRING TOUR WITH A LOCAL BORN & RAISED IN PORTLAND!

   Join our family-owned and operated tour company for a journey along the stunning Maine coast that you won’t forget. With Portland Explorer, every tour is a unique adventure!

   Eric Pray, co-owner and guide, is not just an expert on Portland’s rich history but also a seasoned commercial lobsterman and tuna fisherman. During the off-season, he’s out on the waters, and during the tour season, he brings his love for the sea and deep knowledge of the area straight to you.

   You’ll begin your journey with a fully narrated tour through Portland’s historic Old Port, breaking down centuries of Portland’s past to present as Eric shares stories of this vibrant area, one of North America’s first working waterfronts. Then, enjoy a picturesque drive along the breathtaking coastal waters of Casco Bay. Feel the salty breeze and take in the stunning views. Along the way, you’ll visit three iconic lighthouses along the southern Maine coast. Each one has its own unique story and charm, and they’re perfect for memorable photos.

   Eric’s deep connection to the sea and Portland’s history ensures you get an authentic and enriching experience. As a family-owned business, we treat every guest like family, providing personalized and warm hospitality. Learn about Portland’s 350 years as a center for shipping, fishing, commerce, and travel, making it one of the largest and most important ports in the United States.

   Don’t miss out on this one-of-a-kind tour that combines history, stunning scenery, and the personal touch of a true local. Join us and explore Portland like never before!

The Scenic Route Maine Tours

Portland, maine lighthouse tours.

We are outside the ship terminal

Featured Tours

• Most Popular!
• Clock 2 hours

City & Lighthouse Tour

The best way to get a taste of what our great city of Portland has to offer! A must do!

• Clock 3 hours 30 minutes

Kennebunkport Tour

Enjoy the scenic drive to the lovely seaside village of Kennebunkport; incredibly picturesque and quaint.

Scenic Route Maine Tours is a LOCAL, family-owned and operated Maine Lighthouse tour company sharing what we love about our charming city of Portland and great state of Maine!

Operating since 2012, our stellar Tripadvisor reviews prove that small groups and excellent value combined with premium quality  is a great mix.

Our friendly, fun, and knowledgeable guides love what they do and want to share their excitement with you!

Praise For Our Maine Tours From Tripadvisor

"Well run tour. Guide was excellent with many facts and stories about the area. Great communication from owner leading up to the tour. Would highly recommend"

"Excellent knowledge of area, easy to understand, small and intimate! Fun! Picked up right at pier from cruise line, she had great recommendations for downtown lunch spots too!"

"Great tour. Guide was knowledgeable about the area & shared some fun facts. Kennebunkport area is very quaint & shopping fun. Recommend this tour."

"In Portland for one day on a cruise and took this bus tour to Kennebunkport. It was a very pleasant drive-through with a great overview of a beautiful coastal town and just the right amount of time to walk around the downtown and/or eat lunch. We hope to return to Kennebunkport."

Book 2024 Tour Tickets Here!

Sightseeing Tours in Portland, Maine on a Vintage Fire Engine!

Portland, maine's best narrated city tour.

Embark on an unforgettable journey with Portland Fire Engine Co. Tours, offering distinctive guided sightseeing and history tours in Portland, Maine aboard a Vintage Fire Engine. Immerse yourself in the beauty of Portland’s peninsula as we traverse cobblestone streets, passing by iconic landmarks including Portland, Maine lighthouses, Civil War forts, and captivating historical architectural marvels that define our beloved city. Our 50-minute Portland fire truck tour provides an extensive glimpse into the heart of Portland Maine.

Guided by passionate local tour guides, our Portland fire truck tours offer an insider’s perspective on Portland, allowing you to uncover hidden gems and fascinating insights into our vibrant city. Whether you’re a first-time visitor or a seasoned traveler, our tours are the perfect way to acquaint yourself with Portland upon your arrival. Don’t miss the opportunity to explore our city by the sea in a truly unique and memorable way with Portland Fire Engine Co. Tours!

Our Private Portland, Maine Sightseeing Charters accommodate up to 13 People and offer the most competitive rates in Portland, starting at just $350 !

Plus, you have the freedom to bring your own beverages, food, and music for a personalized experience!

This tour is truly unique! It’s one of just a handful offered throughout the entire United States!

Top Rated on TripAdvisor and Viator for a Portland Maine Lighthouse Tour!

TripAdvisor Travelers’ Choice

Unique Portland, Maine Tours

Experience the history of Portland, Maine like never before with our intimate and fully narrated tours aboard an original Vintage Fire Engine. Explore every corner of the picturesque peninsula including amazing views of historic lighthouses and Civil War forts. A Portland Maine lighthouse tour done right!

• Users 13 Guests
• Clock 50 Minutes

About Our Fire Engine Tours in Portland, Maine!

Welcome aboard Portland, Maine’s only Vintage Fire Engine Tours, where history comes to life! Join us for the finest-narrated history and sightseeing tours that Portland, Maine has to offer. Explore the vibrant past of Portland as we cruise past numerous local landmarks that have defined and shaped its rich history. Along the way, marvel at the majestic lighthouses, formidable Civil War forts, and indulge in the delectable offerings of the amazing restaurants and pubs that grace the streets of Portland. Come along for a truly unique and immersive tour through Portland’s captivating past aboard our open-air Vintage Fire Engine.

So why a Portland Fire Truck Tour?   Our journey began with a vision to showcase the essence of Portland, Maine in a distinct and memorable way. Owner Keith, a passionate history buff and car enthusiast, embarked on a mission to create a shorter, unparalleled touring experience around the peninsula of Portland. Inspired by Portland’s illustrious fire history, Keith retrofitted a vintage fire truck to accommodate 13 passengers safely. With a small group size, the tour feels very personal and family-oriented, making it truly unique. With small group sizes, our Portland sightseeing tours feel very personal and family-oriented, making  them truly unique. Equipped with a large flat-screen TV displaying archival photos of Portland’s yesteryears, our Vintage Fire Engine offers a fascinating glimpse into the city’s storied past. Come along and learn about the four great fires Portland has endured and survived!

With limited capacity seating, be sure to secure your spot early to avoid disappointment. We look forward to welcoming you aboard for a tour experience that will linger in your memory long after you leave Portland.

Experience the ultimate Portland Maine lighthouse tour done right!

These 5-Star Tripadvisor Reviews are on Fire!

Glenn was a great guide and gave us lots of information about Portland! The trip was fun and the fire truck is great!

First time for an extended visit in Portland and this tour with such amazing guides set the whole trip on the right path.

We booked a private tour for our group of 9. We all loved it including our 3 yo. A fun, unique and educational tour of the city.

I had a great time on this tour, it wasn’t too long or too short, the guide gave great info on things to do and the best places to get food!

Excellent commentary and the opportunity to see some of historic Portland. Also the opportunity to see the port from a different perspective.

Our family has enjoyed the tour very much. We've had a great time! We were able to get a glimpse of Portland and look forward to going back to Portal in the future.

I really enjoyed this tour! The tour guide was clever and very personable. I learned a lot about Portland, but was never bored or felt like I was sitting in a lecture. Highly recommend!

16 Awesome Walking Tours in Portland, Maine

Portland, Maine is a beautiful city that’s perfect for taking a walking tour. With its historic architecture, coastal views, and delicious fine dining restaurants , diners , and cafes, there are plenty of sights to take in.

It also happens to be Maine’s largest city, so you get all the energy of a city without all the crowds (well, some places can be kind of crowded).

From a cultural exploration of the city to a jaunt along the waterfront in Old Port, each of the walking tours offers something unique. Whether you’re looking for a leisurely walk around town or an in-depth look at local history and culture, there are tours to suit all interests.

You can choose from a variety of walking tours, including learning about Portland’s cool history , a culinary journey through some of the best eateries in town, or even a craft beer tour .

Whether you’re an architecture buff, a foodie, or just looking for some fresh air and exercise, there’s something for everyone on these fun Portland Maine walking tours.

If you know you are coming to Portland but aren’t sure where to stay, why not opt for a place with an indoor pool? Here are the top-rated hotels in Portland that have indoor pools .

No matter which tour you choose, you can be sure to get an unforgettable experience while exploring the best of Portland Maine on foot. So lace up your shoes, grab your camera or phone, and get ready to experience a wonderful walking tour of the city!

Walking Tours Portland Maine

✅ Walking Tours: Portland, Maine’s History

Exploring the history of Portland, Maine is a great way to really get to know this vibrant city. For those looking for an in-depth look into the past, guided walking tours offer a unique opportunity to explore the historic sites, culture, and stories of the area.

Whether you’re interested in learning about the city’s founding fathers or seeing the grandeur of its post-Industrial Revolution architecture, there’s something for everyone on these informative, educational tours.

With an engaging, and often locally-raised tour guide who shares their passion and knowledge of Portland’s past, visitors will learn about everything from the city’s maritime history to its vibrant food culture.

So put on your walking shoes and get ready to explore the past of this beautiful city!

Walking Tours Portland Maine: History Tours

1. a walk through time tour in portland.

~$50/two ppl

If you’re looking to explore Portland’s history, join this captivating walking tour. You’ll have the opportunity to view many amazing attractions throughout the historic cobblestone streets of Old Port, downtown, and the waterfront area.

Your experienced guide will share intriguing stories of Portland’s rich past. Snacks are provided for all participants and group sizes are capped at 20 people!

Book, or Learn More About A Walk Through Time Here

2. Portland Hidden Histories Walking Tour

~$49/Two ppl

Discover Portland’s unique culture as you explore the city with a local guide. Learn about the tenacious souls who have shaped Portland’s identity through centuries of rebuilding, uncovering stories both inspiring and awe-inspiring.

As you wander down historic avenues, your curiosity for this vibrant destination will be sure to grow! Explore the eons of history in Portland’s historic Old Port and working waterfront on this Hidden Histories Tour!

Feel the palpable presence of Indigenous Wabanaki leaders’ earliest relationships with European colonizers as you are taken through a 1.5-mile route along historic streets like Congress Street, The Old Port, and Commercial Street.

This tour offers an exclusive collection of hidden histories over the course of the 2-hour walking tour that are not offered in other tours. It is sure to be entertaining and informative all at once!

Book, or Learn More About Hidden Histories Tour Here

3. Portland Black History Walking Tour

~$49/two adults

Step back in time and see the journey of the Black Portlanders who strived to move our city, state, and nation toward freedom, democracy, opportunity, and equality.

The success of Maine’s early settlements was propelled by Black labor, expertise and intelligence – all while they continually fought against oppression in order to gain power. Join this guided tour that will walk you through these monumental moments!

Explore the incredible history of Maine and some legendary people of the area with the Portland Black History Tour. With two hours of captivating narration, you will journey 1.5 miles through the Old Port and East End neighborhoods.

You’ll discover stories that are often overlooked in traditional tours- such as those who founded local communities, overturned slavery statewide, drove maritime industries, gained political influence, and fought for equal rights.

Created by uncovering piles of research and historic documents, this tour will open your eyes to a different, and unexpected, history.

Book, or Learn More About Black History Walking Tour Here

4. Portland Women’s History Walking Tour

Portland women have served as driving forces of the city’s culture and national progress toward equality.

Listen to the stories of incredible women, such as the Indigenous Penobscot performer who shifted immigration policy, a Chinese immigrant laundress named American Mother of the Year, a white tavern keeper confronting British Navy ships, and an enslaved Black maid abolishing slavery in her state!

Their indomitable spirit shines through their outstanding accomplishments both within factories and on ballots. Unlock the captivating charm and rich history of a city that was almost lost had it not been for the substantial power of women.

Hear stories told with humor, heart, and abundant enthusiasm by your guide, a Portland native. Explore museums, grand row houses, noble churches, and flawless Federal-style mansions on this two-hour walking tour across 1.3 miles through Portland’s Arts District and West End neighborhood!

Book, or Learn More About Portland Women’s History Walking Tour Here

5. Downtown Portland: Coastal Vibe and Old Mansions

During this self-guided tour, you’ll embark on an enlightening journey as you go back in time to the City Hall, where a rich history awaits.

You’ll be in good hands with your tour guide who will then lead you down Congress Street – Portland’s most celebrated thoroughfare – and introduce you to iconic and historic landmarks such as Monument Square, the Wadsworth-Longfellow House, and the Museum of Art.

Afterward, explore the city’s architectural masterpiece: Victoria Mansion. Boasting an impressive and intricate Italianate design, it is one of the area’s prized attractions. Then, make your way to Old Port, an amazing port district with plenty of historical charm.

Wander through its antique stores, art galleries, and picturesque buildings for hours on end, or enjoy some delicious seafood in any one of its top-rated restaurants! Old Port is one of the best places in Portland to do all those things all within a short distance of each other.

When you return to Congress Street, prepare to be awestruck by the grandeur of the Gothic Cathedral of the Immaculate Conception. You’ll also have an opportunity to climb up the Portland Observatory for unbeatable 360-degree scenic views!

To top it off, the tour will conclude at the Eastern Promenade where spectacular ocean vistas and a myriad of historical monuments await—it’s sure to create lasting memories of your stay in Portland.

Book, or Learn More About Coastal Vibes & Old Mansions Here

Walking Tours Portland Maine: Culinary Tours

✅ Walking Tours: Portland, Maine’s Culinary Scene

If you’re a foodie, then Portland, Maine is the perfect destination for you! With its abundance of delicious eateries and unique culinary experiences, it’s no surprise that many people flock to this city to sample its cuisine-it’s definitely home to the hottest restaurants in the state.

(While Portland restaurants might dominate, there are amazing fine dining spots around the state as well. )

Now, you’ll have the chance to explore the best restaurants in town on foot – with walking tours of Portland Maine’s culinary scene. From enticing seafood restaurants to mouthwatering bakeries, these guided tours offer a tasty exploration of the city’s best eateries.

Learn about the area’s unique food culture as you sample local specialties and get behind-the-scenes looks at some of Portland, Maine’s best restaurants. So grab your appetite and get ready for an unforgettable foodie adventure!

6. Old Port Culinary Walking Tour from Portland

~$140/two ppl

Aspiring epicures can wander through Portland’s picturesque Old Port on their own, but to expose the city’s hidden gems and authentic culinary delights, a Maine foodie tour with a reliable guide is the best bet.

Uncover all that Portland has to offer with this guided foodie tour. You’ll visit up to six eateries and tantalize your taste buds with enough samples for an entire meal! With one exciting tour, you get an unforgettable experience of some of Maine’s finest fare.

With no more than 14 travelers, you’ll get familiar with the local food as your guide regales stories about Portland’s lively culinary scene. Visit five to six eateries along Commercial Street in the heart of Old Port and savor delicious Maine-inspired cuisine!

Book, or Learn More About The Old Port Culinary Walking Tour Here

7. Donut Tasting Walking Tour: Portland’s Old Port

~$45/two ppl

Portland, Maine has made a name for itself as one of the top culinary hotspots nationwide. Okay, so you might not think of donuts when you think culinary tour, but that would be a mistake!

On this tour, you’ll get an awesome opportunity to savor some of the city’s best donuts while also gaining insight into its remarkable history! Your guide will take you to The Holy Donut (famed everywhere!), and you won’t have to wait in line!

You’ll also visit other local favorites that are equally delicious. What an awesome memory–an unforgettable journey through Portland’s delectable doughnut scene!

Book, or Learn More About Donut Tasting Walking Tour Here

✅ Walking Tours: Portland, Maine’s Beer Scene

Portland, Maine is becoming a well-known destination for its craft beer scene. With so many breweries to choose from, it can be hard to know where to start. But now, visitors can explore the city’s best beer offerings on foot!

Guided walking tours of Portland Maine’s beer scene offer a unique opportunity to get in some craft beer tastings while learning about its history. Get an insider look at the area’s breweries as you sip your way through this beautiful city.

So grab a map and get ready for an adventure that takes you to the best beer spots in Portland!

8. Old Port Walk, Talk, and Taste Brewery Tour

~$87/two people

Take a guided, leisurely, walking tour and discover the storied past of Portland’s waterfront.

Explore prohibition-era landmarks as you learn about importing goods to the area while sampling delicious beer from three iconic local breweries: Shipyard Brewing Company, Gritty McDuff’s, and Liquid Riot Bottling Company.

Travel in small groups with an experienced local guide on comfortable minibuses (though you are walking for the tour of the breweries) for maximum enjoyment. Snacks and beverages are included throughout your journey, plus convenient pickup services at our centrally located meeting point!

Book, or Learn More About Old Port, Walk, Talk, and Taste Tour Here

Walking Tours Portland Maine: Scavenger Hunts

✅ Walking Tours (sort of): Do a Portland, Maine Scavenger Hunt

Like a self-guided tour but better, because you get to experience the sights and sounds of Portland, Maine like never before – by taking part in a fun-filled scavenger hunt at your own pace! Guided scavenger hunts are a really fun way to explore this charming city.

As you wander through the streets of Portland, you’ll get to experience its vibrant culture while discovering hidden gems tucked away in unlikely places. With exciting tasks to complete and interesting facts about the city to uncover, you’ll have a blast as you make your way through town.

Portland is full of surprises, so take part in this unique activity and explore the city like a local. With the help of your friendly (remote) guide, you’ll get to experience Portland from a new perspective and gain a better understanding of its culture and history.

And with fun tasks to complete along the way, you’re sure to have an adventure you won’t soon forget. So grab your map, pick up a few clues, and get ready for an unforgettable scavenger hunt in Portland, Maine!

9. Portland Scavenger Hunt: The Maine Event

~$12/ two ppl

Are you craving a thrilling outdoor activity in Portland? The Let’s Roam scavenger hunt app has the answer! Whether you’re from here or somewhere else, this is sure to make a fun afternoon of wandering the city.

Get ready for some exploration on foot and discover what Portland has to offer. See if you have what it takes by taking pictures, racing against time limits, and navigating your way through locations like Congress Street and Old Port with The Maine Event Scavenger Hunt!

Book, or Learn More About The Maine Event Scavenger Hunt Here

10. Portland, Maine Madness Scavenger Hunt

~$28/two ppl

Unlike with most scavenger hunts, guests get their own remote host to help and motivate them along the way. These specially crafted adventures blend tour-like elements with creative challenges and detective hunts that the whole family can enjoy.

You’ll uncover off-the-beaten-path gems and creatively interpret clues related to art, history, and culture – all for points! Ready to take your talents global and make a name for yourself? You can compete with teams from all over the world for international fame and glory!

Plus, even if there’s no competition in sight near where you live, it doesn’t mean that fun should be out of reach. You’ll still get a chance to shine by showcasing your favorite hangouts or uncovering unusual oddities along the way.

Book, or Learn More About Maine Madness Here

11. Scavenger Hunt in Portland, Maine by Zombie Scavengers

Are you ready to face the ultimate challenge? Portland is calling and it needs your help! With Zombie Scavengers, you will have the opportunity to explore this city in search of essential items required for surviving a zombie apocalypse.

You’ll earn points each time you find something – but that’s not all: complete some thrilling zombie-themed challenges on the app for extra points! Strategize carefully if you want to amass as many points as possible and avoid becoming a victim of this merciless apocalypse.

Don’t worry; they’ve got your back with their remote host available through chat in case anything goes wrong. So, can YOU survive an epic battle against zombies in Portland?

Book, or Learn More About Zombie Scavengers Here

12. Unique Wacky Walks Scavenger Hunt

~$10/two ppl

Join Wacky Walks on an exciting scavenger hunt around Portland and become the King or Queen of your group as you compete with others. The app-based game will lead you to locate hidden items in the city while also completing fun tasks along the way.

As a reward for finding each item and finishing these missions, points are awarded to players. Gain the highest possible score and be crowned King or Queen of Portland for a day by playing Wacky Walks!

With no time limit, take your time exploring the city as you play. Not to worry if you need assistance – the host will always be on hand through chat support.

Book, or Learn More About Wacky Walks Scavenger Hunt Here

13. Crazy Dash Scavenger Hunt Adventure

Discover Portland like never before with Crazy Dash! The app and the remote host provide a checklist of thrilling tasks to complete and exciting locations to explore. You are free to visit them in any order you choose, earning points along the way for each challenge completed or object found.

Best of all, there is no time limit on this laid-back adventure, so you can take your time exploring the fantastic city that is Portland! In addition, the helpful remote host will be available throughout your game if assistance is ever needed.

Book, or Learn More About Crazy Dash Scavenger Hunt Here

14. Operation City Quest Scavenger Hunt

Ready to discover Portland? Look no further than Operation City Quest! Download the app and complete tasks all around the city for points. Whether you decide to start with an item or challenge is completely up to you!

Track your progress on the leaderboard, and don’t forget about the helpful remote host ready via chat if problems occur during your journey.

Book, or Learn More About Operation City Quest Scavenger Hunt Here

15. 3Quest Challenge Scavenger Hunt

Take a tour of Portland in an entirely unique way, with the 3Quest Challenge! Download the app and explore the city following clues written as riddles. As you complete tasks, collect points to check your ranking on the leaderboard.

Whether competing with friends or colleagues, find out who will be crowned victor at this exciting scavenger hunt! Take on three quests and explore the city of Portland in just two hours! All you need is your wits, and a remote host to assist virtually along the way.

Divide up objects and tasks into 3 different excursions: first quest, second quest, and third quest; finish them one by one to complete the game. Set yourself a time limit if you want more of a challenge!

Book, or Learn More About 3Quest Challenge Scavenger Hunt Here

16. Portland Freedom Trail

$0/Self-guided

Experience Portland, Maine’s history and culture like never before with a self-guided walking tour on the Freedom Trail. This exciting journey takes visitors through some of the city’s most significant locations and attractions, highlighting important stops along the Underground Railroad.

Learn about this powerful movement as you explore churches, schools, homes, and businesses that played a role in helping thousands of enslaved African Americans find freedom. You’ll also gain a better understanding of the city’s past.

Get The Self-Guided Portland Freedom Trail Map Here

Conclusion: Walking Tours in Portland Maine

As you can tell, there are many Portland walking tours for you to choose from–Maine foodie tours, brewery tours, educational tours about the (surprising stories) and people who made Portland what it is today, and some plain old fun tours like the scavenger hunts.

If walking tours of Portland aren’t your thing, maybe a boat tour of Casco Bay, or a bus tour of local breweries is more your style.

No matter what you choose, you’re sure to have a great time sightseeing and learning something new on any of these Portland tours. It’s an amazing city, and experiencing it on foot is really the best way to tour Portland.

If you’re not from the area and want to avoid having to take a car at all, here are some great Portland hotels with free airport shuttles . Several of the hotels are right downtown, too! This means you could spend all your time without the hassle of renting a car.

If you want to venture a little further away, in the winter, why not try some great skiing just a couple of hours away? During the other seasons, Portland is still close enough that you could take a day trip to Acadia National Park !

Get Your Guide To 7 Beautiful Sandy Beaches In Maine

Meet the heart and soul behind Wandering Through Maine – a true New Englander at heart, originally from NH, who found their forever home in the beautiful state of Maine. Maine called to them like a lighthouse beacon, and they've embraced it wholeheartedly ever since. This blog isn't just a guide; it's a heartfelt invitation from someone who's walked the trails, sailed the waters, and knows Maine not just as a place on the map, but as a vibrant community and an adventurer's paradise that they call home.

I Just Visited Portland, Maine: Here’s What I’d Do Differently

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Stay at a waterfront hotel in the downtown area of old port, prepare, prepare, prepare, budget accordingly.

Last weekend, I visited Portland, Maine, and I made a few mistakes—but at least that means you don't have to! Don't get me wrong, there was certainly a lot that I loved about my visit, including fresh and delicious seafood, breezy and boozy boat rides, and shopping for lobster-themed souvenirs in the adorable downtown area of Old Port.

During my visit to Portland, I briefly traveled outside of the city to Boothbay Harbor, but there are certainly other 1-day road trips from Portland you can take as well as further unique places to visit in Maine if you'd like to make the most of your time in the state. P.S. Did you know that there's even a desert in Maine ?

There's no doubt in my mind that I will return to Portland one day with my newfound knowledge of what not to do for a great visit to the seaside town. However, I'm sharing that valuable knowledge with our readers so you don't make the same mistakes I did and can have an even more enjoyable visit.

7 Scenic Waterfront Small Towns In Maine To Retire

Retire in tranquility by the water in Maine's picturesque small towns. Explore these idyllic destinations offering scenic beauty and coastal charm.

Lesson #1: Research is a must (and splurge for that hotel)

When I first booked this trip, I noticed the hotel prices were much higher than I expected for a random weekend in Portland. That being said, I opted for a lower-budget hotel, which wasn't located in the downtown area.

The short of it is this: you get what you pay for. The hotel I booked was a few hundred dollars cheaper per night than the waterfront hotels in Portland, but I ended up paying in another way; I wound up with bugs in my hotel room. What a nightmare!

A common traveler mistake is not doing proper research before booking. Because I'd been eyeing hotel costs for a couple of weeks, I eventually became eager to simply book something, no matter the place. However, if I only did a quick read over the Google reviews of this hotel, I would find that other guests had experienced pests in the rooms too. You know what they say: for every bug you see, there are 10 you don't!

Luckily, they weren't bed bugs, which would have been the worst-case scenario. I typically check Orkin's hotel bedbug registry before booking. However, it's also possible that the hotel hasn't made its way to the list yet (which is why I always check the mattresses in my hotel room as soon as I check in; I untuck the sheets, look for blood marks, insect feces, check the box spring, and all areas around the bed).

Nonetheless, any bug present is a sign that cleanliness is lacking, and being in a dirty place isn't exactly something that helps anyone rest their head at night. For a hotel with a reputation you can feel confident about, try one of these best hotels in Portland .

Though this was secondary to the unwanted guests in my hotel room, I had to drive everywhere I wanted to go since my hotel wasn't in the downtown area of Old Port. Typically, I like staying within walking distance of the area in which I will spend the majority of my time to truly experience the place I am visiting.

Lesson #2: Allow room for error and bring the right gear

My primary reason for visiting Maine was to see the beautiful Atlantic Puffins in Boothbay Harbor. Though I allowed a 30-minute time buffer, there was excessive traffic getting on the only bridge to the island, which caused me to worry that I might not arrive on time.

When I called ahead to alert the cruise company to my dilemma, the manager said he could only hold the boat for a couple of minutes past the departure time. In addition, he held a parking space for me at the front of the lot next to the pier. Though this worked out in the end, take this as a lesson: Leave plenty of time to arrive at your destination.

Once I got comfortable with a cocktail on the boat, I realized my big mistake: I forgot to pack my binoculars, and every birdwatcher knows that binoculars are a must. There were plenty of puffin sightings as well as views of other birds, however, binoculars could have allowed me to see more details.

Binoculars aren't just for birds, though; a pair would have also been nice for the lighthouse cruise. Seeing lighthouses is a must in Portland; either plan to drive to one or take a cruise with picturesque views like I opted to, it's a great way to get a view of a few of the islands in Maine .

The following day I went to East End Beach, stopping to take photos of the historic trains chugging by along the way. I plopped down a hotel towel until the sun's heat finally pushed me to take a dip in the water.

I made the unfortunate mistake of tip-toeing my way across the sand in my bare feet, causing my feet to get cut up on some jagged rocks. Foot protection is a must on Maine's rocky beaches. Water shoes, Crocs could even work if you put them in sport mode, or any footwear that ensures you won't lose your shoes in the waves are definitely a must. I'm still rubbing Neosporin on my cuts.

Portland, Maine To Bar Harbor: 12 Things You Should Pull Over To See On The Way

There are many things to do between Portland, Maine, and Bar Harbor, from exploring beaches and trails to seeing state parks and quaint seaside towns.

Lesson #3: Have a plan for what you're willing to spend money on (and what you're not)

My last word of advice is to bring extra cash. Had I properly budgeted for emergency purchases, I could have purchased binoculars and footwear at a shop in the downtown area; these businesses know when their customers are primarily tourists and therefore price their goods accordingly to maximize profits.

So, what did I spend my money on instead? Well, the bulk of my budget went to the expensive seafood dishes I ordered at restaurants—but c'mon, you can't go to Maine and not order lobster! When lobster is the main course , you can expect your entrée to cost you more than the average meal.

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I tried 5 of the most famous lobster rolls in Portland, Maine. Here's how they all ranked.

I recently visited Portland, Maine, for the first time and tried five local lobster rolls.

They all ranged in price and preparation, though I tried most of them in the classic Maine style.

My favorite lobster roll had the best signature seasoning.

Nothing says summer quite like a lobster roll on a seaside dock, the sound of seagulls cawing overhead.

However, an authentic Maine lobster roll doesn't come cheap.

On a recent trip to Portland, Maine , I set out to find the absolute best lobster roll around. Most of them were at least $30 — a price that may be too steep for some of the millions of tourists who venture to Maine's coastline each year to indulge in regularly throughout the summer.

So if you're only going to try one, you'll want to know which one is the absolute best.

I tried lobster rolls from five of Portland's most famous spots and ranked them. All except one were traditional Maine-style rolls , which meant they were served cold and with mayonnaise. The other most popular style of lobster roll is Connecticut, which comes warm with melted butter.

Here's how the lobster rolls ranked based on price, taste, and atmosphere.

The first stop on my lobster roll tour was The Highroller Lobster Co.

Highroller may have started out as a simple hot-dog cart, but it has since grown into an institution in the heart of Portland. In its Best of 2024 Awards, Portland Old Port named Highroller Lobster Co. the best lobster roll in the city, making it a must-try spot on my list.

Located on Exchange Street, the building's exterior beckoned me with its can't-miss red branding and playful sidewalk sign.

In addition to indoor and outdoor dining, guests can also order takeout or grab some merch at the restaurant's adjoining gift shop, which I thought was unique and geared toward Portland's many tourists.

The interior of The Highroller Lobster Co. was modern and reminded me of a vintage diner.

The restaurant had an ordering stand where you could place orders with an employee, as well as QR codes on every table that allowed you to place orders online and have them delivered to your table.

The design style of the dining room reminded me of a '50s diner, with a modern twist thanks to the black wood floors and glittering disco ball overhead. It was a warm day, so I decided to sit out on the back patio to eat my lunch.

The lobster rolls from Highroller were able to be completely customized.

The Highroller Lobster Co. was unique in that practically every element of the lobster roll was customizable, from the amount of lobster meat to different flavors of mayonnaise and other sauces, such as mango habanero mayo, garlic mayo, and lobster ghee.

However, for the sake of this ranking, I decided to keep it classic.

I ordered the four-ounce lobster roll with regular mayonnaise. The lobster roll cost $30, excluding tax and tip. I also ordered a side of fries for an extra $5 and a soda for $3.

The toasted brioche bun impressed me, but the thick layer of mayonnaise on top of the roll threw me off.

While I do like mayonnaise, and don't really have a preference when it comes to Maine-style versus Connecticut-style lobster rolls, I thought there was just a touch too much mayonnaise on this roll.

It also veered on the thick-and-gloopy side, rather than simply dressing the lobster meat.

I'd still come back to Highroller, but I'd probably customize my lobster roll differently next time.

I thought the mayonnaise covered up a lot of the flavor of the lobster meat itself, which was a shame considering the meat was juicy and thick. However, the toasted bun had a delightful crispiness to it and held the roll together perfectly.

Overall, it was a solid lobster roll, just not quite my favorite.

While I wasn't ranking the fries, they were perfectly seasoned and crispy. They were, without a doubt, my favorite of all the sides I tried throughout this ranking.

My fourth favorite spot was Portland Lobster Company, located right in the heart of the Old Port.

Portland Lobster Company was also nominated this year by Portland Old Port for the best lobster roll category. It has won multiple "Best in Portland" awards in the past, including best lobster roll and best place to take out-of-towners.

Centrally located to many of Portland's biggest attractions, from dockside dining to boat tours, the restaurant was right on the water.

I could imagine this was a very popular spot for tourists to grab lunch since it was right on the pier on one of the busiest streets in the city.

It was prime lunchtime on a Saturday, but I was still able to grab a table outside overlooking the water.

A live band was playing on the outdoor deck. By far, this spot had the most classic New England atmosphere, from the casual seating to the ordering counter and tables overlooking the Portland pier.

To my surprise, Portland Lobster Company's signature lobster roll was served with warm butter.

The menu said the lobster roll was made with meat from a one-pound lobster brushed with sweet butter. The lobster meat came on a classic roll with lettuce, lemon wedges, and fries on the side.

It was labeled on the menu as market price, but I got it for $27.99, excluding tax.

I thought the lobster meat really stood out.

No other ingredients, like the mayonnaise in the last roll, were competing with the lobster to be the star of the show. I liked the warm butter, which coated the bun and enhanced its flavor.

However, while the lobster meat did have a nice flavor, I thought the texture was just a touch on the rubbery side.

This was a good, classic lobster roll, but it wasn't anything unique.

This lobster roll was a good, classic sandwich I could see myself getting again the next time I'm in Portland. It hit many of the marks, especially when it came to price and the restaurant's ambiance.

However, there wasn't anything especially unique about this lobster roll. While Highroller wasn't my favorite either, I at least appreciated that they were taking some risks with their flavor offerings. At Portland Lobster Company, there was only one way to order this roll — and it wasn't even served in the classic Maine style with mayonnaise.

To me, the best part of choosing this spot was the location. From the convenience of being located right downtown to the waterside seating and seagulls cawing overhead, I couldn't imagine a better spot to grab a lobster roll in the summer.

Bite Into Maine, located slightly outside downtown Portland, landed in the middle.

Named by Food & Wine as offering the best sandwich in Maine, Bite Into Maine has multiple locations in the area, including a food truck near Portland Head Light, the oldest lighthouse in Maine, in Cape Elizabeth.

We stopped by the location in Munjoy Hill, the restaurant's only brick-and-mortar location.

The restaurant looked like a shipping container and was located next to other businesses. The overall vibe of this part of town felt industrial, rather than the historic, classic New England feel I got downtown.

The restaurant was modern, and it was easy to place my order.

I ordered at the counter and waited at a nearby table for my name to be called. The restaurant was bright and clean.

However, I admittedly missed some of that classic seaside feel I got at Portland Lobster Company and the other locations. I could have been anywhere in the country, from Ohio to Maine, inside this restaurant.

I was really impressed by Bite Into Maine's classic Maine lobster roll.

I ordered the 6-ounce Maine lobster roll for $37.95, plus tax, making it the most expensive roll I tried.

Even though the Maine-style roll is served with mayonnaise, all the buns at Bite Into Maine are butter-grilled, which I thought gave me the best of both worlds.

The lobster meat was spilling out of the roll when it arrived.

It came topped with green onion, which made the lobster roll beautiful to look at. The lobster meat was perfectly dressed with mayonnaise — it was light and fresh and enhanced the flavor rather than detracting from it.

I thought the extra-large size was definitely enough to feed two people.

I loved this lobster roll, but the ambiance at the restaurant was lacking for me.

I had no complaints about the lobster roll and thought the price was worth the amount of meat it contained.

However, I couldn't get over the fast-food feel of the restaurant — but I know this was just my personal preference and opinion. When I'm in Maine eating a lobster roll, I want to really feel that vibe.

The next time I come back to Maine, I'll stop by one of the chain's food trucks, especially the one near Portland Head Light. I think that would dramatically improve my experience, and could even take this lobster roll all the way to the top of my ranking.

The Cousins Maine Lobster food truck is located right at the base of Portland Head Light in Cape Elizabeth, just across Portland Harbor.

Cousins Maine Lobster is one of the most recognizable lobster brands in the country, with more than 50 locations across 26 states. The only Maine location is a food truck located in Fort Williams State Park, a popular site for Portland visitors and the location of the oldest lighthouse in Maine.

In addition to lobster rolls, the food truck offers other menu items, such as lobster tacos and lobster tater tots, which appeared to be popular options for families wanting to split something.

The location really blew me away.

Situated right at the base of the lighthouse, the food truck was in proximity to walking trails and spots to look out over Portland Harbor and Maine's rugged coastline. It didn't get any more New England than this.

I ordered the classic Maine-style lobster roll.

The lobster roll came with a lemon wedge and was served chilled on a roll with a "touch of mayo," the menu on the side of the food truck stated. It cost $23.99, excluding tax.

The meat was succulent and juicy and came with just the right amount of mayonnaise.

To me, this lobster roll exemplified the best of what makes a classic lobster roll good, as well as an excellent location and price.

The large pieces of lobster meat practically melted in my mouth, and I thought the light smearing of mayonnaise inside the roll brought it all together.

I'd be perfectly satisfied if this was my only lobster roll of the summer.

From the prime seaside location to the price and the classic nature of this lobster roll, it truly did hit all of the marks.

My only complaint, however, was with the roll. I think I preferred the butteriness of some of the other rolls, and while this one was adequate, it wasn't my favorite.

My favorite lobster roll came from Luke's Lobster, located right on Portland Pier.

The Portland Pier location is Luke's Lobster 's flagship location, though the chain actually started in New York City with a tiny lobster shack.

There are now restaurants all across the northeast, but the Portland restaurant is well known for its dockside location with panoramic views of the harbor.

It's also gained quite a reputation around town . In 2023, local residents  voted it  the best lobster roll in Portland .

When I told locals I would be trying different lobster rolls and determining the best one, nearly all of them had the same question: "Have you been to Luke's yet?"

This certainly set the stage for what I hoped would be a memorable lobster roll.

I thought Luke's Lobster had the best atmosphere out of all the places I tried.

There was lots of seating inside and outside the restaurant when I went on a weekend, so I think it's pretty easy to get a table — something that's valuable when it comes to peak tourism season in Portland.

Inside the restaurant was clean, modern, and bright, but warm wooden accents and views of the water prevented the space from feeling clinical.

I ordered the Maine-style lobster roll, which Luke's Lobster calls its "claim to fame."

It came with chips and a pickle on the side and was available in two different sizes.

Like the other places I tried, I ordered the largest size available, which was the 6-ounce roll. It cost $37, excluding tax.

The lobster roll came piled high with meat, which was dusted in the restaurant's signature seasoning.

Luke's signature seasoning is made with celery seed powder, sea salt, and garlic powder.

The seasoning on top of the roll really amplified the salty, briny flavor, giving this lobster roll a unique taste.

This lobster roll certainly lived up to the hype.

The meat was succulent and plentiful, and though there was a light mayonnaise dressing holding the meat together, the lobster really spoke for itself. The bun was crispy, and I thought the chips also had a delightful crispy texture that complemented the roll.

From the location to the price to the roll itself, Luke's Lobster really impressed me. It was classic, with a unique twist, and it came with harbor views that really made me feel like a Mainer.

Read the original article on Business Insider

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12 Deering Street #3,  Portland, ME 04101

Single Family

Cheryl Pelletier

Tim Dunham Realty

Last updated:

August 26, 2024, 11:46 PM

About This Home

Nestled in the heart of Portland's Arts District and part of the historic 'Doctor's Row,' this charming townhouse-style condo spans the second and third floors of this 1870 Victorian, offering sunlit rooms with city views. The unit comes with two off-street parking spaces which have been equipped with an electric car charging station. The ornate entrance leads into a sunlit entryway featuring hardwood floors, two bedrooms, large closets, a full bath with clawfoot tub, and a laundry area. The original wooden stairs and curved banister take you to the meticulously maintained third floor, which includes a spacious and sunny living room with an electric fireplace, a home office with built-ins, a formal dining room, open kitchen with Bosch appliances and breakfast bar, a pantry, newly renovated full bath, a large storage closet, and even a private stairway to the rooftop where you can overlook Back Cove and the city of Portland. Four Mitsubishi Heat Pumps/AC efficiently provide heat and cooling year-round. At 12 Deering Street, you're just steps away from some of the best restaurants and museums, as well as everything else the city has to offer.

Built in 1870

Price Summary

$416 per Sq. Ft.

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1,561 Sq. Ft.

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Trolleys are heated and stay quite warm, but do not have air conditioning. They do have big, open windows that provide a very nice breeze once we get moving.

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