boston harbour island tour

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. . . where you can walk a Civil War-era fort, visit historic lighthouses, explore tide pools, hike lush trails, camp under the stars, or relax while fishing, picnicking or swimming-all within reach of downtown Boston. Youth programs, visitor services, research, wildlife management, and more are coordinated on the park's 34 islands and peninsulas by the Boston Harbor Islands Partnership.

Plan your adventure at Boston Harbor Islands National and State Park.

Last updated: March 31, 2022

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Boston Harbor Islands National and State Park 21 Second Ave Charlestown, MA 02129

617 223-8666

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A Guide to the Boston Harbor Islands

How to get the biggest bang for your staycation buck.

From day trips to weekend getaways, our biweekly Traveler newsletter shows you the best of New England and beyond.

Illustrations by Always with Honor

Spectacle Island

The great outdoors have never been so close. This 105-acre spit of natural beauty boasts 5 miles of hiking trails, the highest hill in the harbor, and a scenic beach where you can take a dip without losing sight of the skyline.

Peddocks Island

From June through September, Peddocks is among the four islands that offer primitive camping, sans showers or modern toilets. No tent? Act early to book one of Peddocks’s six-­person yurts—reservations tend to fill up months in advance.

Georges Island

Spend some time exploring Fort Warren, once a prison for Confederate soldiers during the Civil War. To this day, the lure of the Lady in Black—the ghost of Melanie Lanier, a tall-tale character who was allegedly hanged on the island after a botched attempt to bust her rebel husband out of the prison—attracts paranormal aficionados.

Little Brewster Island

One of the outermost islands in the harbor, Little Brewster is home to America’s first lighthouse. Boston Light still shines bright today—its beams can be seen from 27 miles away. Getting out to this island can be tricky: Ferries are only available as part of island tours, which run from mid-June through early October.

Frequent Flyers

More than 200 types of birds have been identified on the islands. Try spotting these species.

Degree of Difficulty ☀ Beginners welcome. ☀☀☀☀☀ Requires Audubon-level determination.

Keep your eyes peeled for this common songbird’s rich blue-and-black plumage.

Red-Tailed Hawk ☀☀

With an average wingspan of 4 feet, this ubiquitous raptor can also be seen stalking prey throughout the city.

American Oystercatcher ☀☀☀

A name like that needs a beak to match. Make a correct ID by paying attention to the long red bill and stout legs.

Red-Bellied Woodpecker ☀☀☀☀

Look to the trees for this woodpecker’s mohawk-like streak of red, which runs down the nape of its neck.

Red Knot ☀☀☀☀☀

A long-distance flyer that travels 9,300 miles from the Arctic to the tip of South America, this bird makes the occasional pit stop here.

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Boston’s downtown real estate is collapsing. this is ominous., our guide to the 12 best restaurants on nantucket, who is “free karen read” blogger aidan “turtleboy” kearney, portland’s sea bags sets sail with sustainable style, in this section.

BOSTON SAILING TOURS

Full Day Sailing & Island Experience

Private Sailing Charters for up to 6 guests around Boston Harbor & Islands

We will sail to the islands that are not accessible by ferry. Depending on the wind, tide, and your preferences we will stop at Lovells, Bumpkin, or Grape islands.

Lovells island is more about the beaches and hiking along the coastline, Bumpkin and Grape more about wildlife. And All of them offer picturesque scenery.

There is, most of the time nobody, or very few people on the islands. You will get to spend a few hours a shore while the boat will be waiting for you.

On the way back, we will take a different route. At all times you will be welcome to participate in the navigation.

Rates: 20% is due at the time of booking. The remaining balance is due at the time of charter.

• Weekdays From $ 950.00   

• Weekend & Holidays $1095

• Duration: 6 Hour Charter

• Price includes up to 6 people

• All ages welcome

Charters depart from JSeaport Water Taxi Dock

142 Pier 4 Blvd., Boston, MA 02210

• Plenty of parking nearby.
• Please arrive 15 minutes prior to your scheduled sail time.
• If you are running late, please call 617-279-3981 to notify us as soon as possible.

Weather Policy

• We want you to have the best experience and will only sail in moderate conditions.
• Occasional light rain clouds wind and seas are part of the New England nautical weather experience.
• Only the captain based on his experience has the discretion to cancel a trip for inclement weather.
• You will be informed within 2 hours prior to the trip if there is any concern.
• If the trip is canceled by inclement weather, you will have the option to reschedule or get a full refund.
• We reserve the right to cancel a trip for unforeseen circumstances, in this case, you will be fully refunded.

OUR POLICIES

BOOKING RESERVATION:

• 20% DEPOSIT IS REQUIRED AT THE TIME OF BOOKING.

CANCELLATION POLICY:

• 48 hours prior to the charter, You will receive a full refund minus 10% of the total value of the trip.
• Less than 48 hours, No refund is available
• A no-show is considered a cancellation.

LIFE JACKET POLICY

• Boston Sailing Charters strongly recommends the use of our USCG-approved life jackets for all passengers while on board. We will provide a life jacket to any passenger wishing to wear one.
• Passengers twelve and under are required by law to wear life jackets while on the vessel.
• Parents or guardians are responsible for determining if their minors between the ages of 13-17 must wear a life jacket.
• The person booking the charter is required to share our life jacket policy with all members of their group.

ALCOHOL/DRUG POLICY:

• Customers are welcome to bring beer or wine. No hard liquor
• Per Federal regulation NO marijuana or marijuana-containing products. No illicit drugs

ADDITIONAL TERMS AND CONDITIONS

• Infants and children, regardless of age, are included in the six-person maximum allowed on board. This is a requirement by the United State Coast Guard.
• Gift Certificates are non-refundable and are valid from the date purchased until October 31st of the following charter season.

WHAT SHOULD I BRING?

CONSIDER TO BRING

• Sailors should dress for safety, comfort, and weather. In spring and fall, dress in layers and bring a jacket or sweatshirt; it can be cooler at sea than on land.
• In summer, bring a hat, sunglasses, and sunscreen. 
• For safety and comfort, soft-soled shoes like boat shoes or sneakers are the preferred footwear aboard the Francesca. You will be asked to go barefoot for safety reasons if you wear hard-soled shoes or high heels on board.

WHAT NOT TO BRING

• Per Federal regulation no marijuana or marijuana-containing products no illicit drugs
• No Hard Liquor

FOOD, DRINKS, MUSIC

• You’re welcome to bring your favorite food, drinks, and music.
• We recommend easy-to-eat items and canned drinks. 
• We do not have a formal table in the cockpit
• We have complimentary water and sodas on board

MOTION SICKNESS

• It is very unlikely to get seasick on the harbor. If you think you are extra sensitive consider limiting your trip to the 2-hour Harbor sail.

WHAT IF I AM RUNNING LATE

• We will always wait for you. However, we will conclude your sail at the scheduled finishing time.

PETS & TIPPING

• Pets are welcome aboard if they can sit on your lap at all times.
• Tips are graciously accepted.

BATHROOM:  Bathroom in the Cabin

Departing Location

Seaport Water Taxi Dock

Mailing Address:

28 Constitution Road

Charlestown, MA. 02129

617-279-3981

[email protected]

© ALL RIGHT RESERVED BOSTON SAIL TOURS OWNED & OPERATED BY CGN MARINE LLC. | SITE DESIGN BY  NXTMEDIA

Passions and Places

A travel + outdoors blog

Paddling through History: A Kayak Tour of the Boston Harbor Islands

May 26, 2016 By Ryan Victor 4 Comments

Back in the 1980s, Boston Harbor was one of America’s dirtiest . Raw sewage was routinely released directly into the water, just outside the shores of the city’s idyllic North End.

Fortunately, the Clean Water Act put an end to this, leading to the construction of the Deer Island Sewage Plant (with its iconic egg-shaped buildings that are visible when flying into Logan Airport) and a 10-mile-long pipe to send the treated waste out to the faster-moving water of Massachusetts Bay.

These cleanup efforts have made Boston Harbor, with its islands rich in history, a premier kayaking destination, and one that’s ripe for exploration.

Thompson Island

Spectacle island, long island, lovell’s island, rainsford island, peddocks island, the outer harbor, kayaking boston harbor.

Boston Harbor is loosely divided into the inner harbor, historically the city’s main port, and the outer harbor, which is more difficult to reach and characterized by rockier islands. The inner harbor contains more historical sites and calmer waters, but the outer islands offer privacy and untouched landscapes.

To kayak the Boston Harbor Islands, there are three main put-in points: South Boston, Deer Island, and Hull. In South Boston, the best place to start is at Carson Beach, which has a parking lot.

In theory, you can rent a kayak or stand-up paddleboard from Boating in Boston there, but the liability agreement prohibits taking the boats into open water. It may not be strictly enforced, but that’s the rule. (Of course, that’s not a concern if you have your own folding kayak that can be easily transported through the city!)

The Deer Island and Hull (Pemberton Point) locations are farther from the city, but both have free parking–plus the advantage that they’re a much shorter paddle to the islands of the outer harbor.

Let me be clear: the harbor is not a place to learn how to sea kayak . It’s a busy waterway filled with cargo ships, yachts, and fast-moving ferries. In strong winds, the waves can become significant and would be a struggle for beginner and even intermediate kayakers.

That said, the harbor is full of interesting islands that can be enjoyed, with a bit of planning, by anyone with some sea kayaking experience.

Assuming you leave from South Boston, the first stop on a tour of the inner harbor is Thompson Island – home to Boston’s Outward Bound program . It’s one of the most developed islands, with dormitories, classrooms, a conference center, and obstacle course equipment set up for the program.

You can hike the miles of trails on the island and relax on its beautiful beaches when it’s open to visitors (weekends from Memorial Day to Labor Day). There are no public bathroom facilities or places to buy water, though, so plan accordingly.

The next stop is Spectacle Island , a hundred acres of parkland and a great place for a picnic or a run on its five miles of trails. With lush green hills and amazing views of downtown Boston, you’d never guess the island’s past. In the 1800s, it had two hotels – and the remote location made them prime spots for gambling and prostitution, until they were eventually shut down.

In later years, a horse rendering plant was built, followed by a trash incinerator. Following this trend, the island was used as a garbage dump between the 1930s and 1960s, and the site was then left to rot for another thirty years.

Spectacle island got a much-needed makeover starting in 1996 during the Big Dig project, when dirt excavated from the tunnels dug in Boston was used to cover up the trash heap. It’s amazing to see how a place with such a sordid past has been converted into a beautiful landscape.

For kayakers, it’s a great stopping place to get out and stretch your legs or just hang out on the gravel beaches.

Tourist season on Spectacle Island lasts from May to October, when a ferry operates from Long Wharf in Boston ($25 round-trip). There’s a snack cart during those months and free yoga classes on Saturdays, as well as bathrooms and beach showers that are open to the public, but it can get a bit crowded. Visiting at other times of year means fewer amenities, but you’ll likely have the place to yourself.

Long Island , officially off-limits to the public, had also many uses over the years: military fort, homeless shelter, Boys and Girls Club camp, and substance abuse recovery center. It was also a source of inspiration for the movie Shutter Island , which was actually shot on Peddocks Island (see below) farther out in the harbor (though a Dropkick Murphy video was filmed in one of its abandoned buildings).

Previously, Long Island could be accessed via a large steel bridge jutting out from a neighboring island, but it was condemned and then removed last year. While you can’t disembark onto the island, many of the structures built for its various uses can be seen from the water, giving another glimpse of Boston’s past.

Lovell’s Island is perhaps my favorite island in all of Boston Harbor because it’s so untouched. And, as is the case with almost all of the harbor islands, it has quite a bit of history.

It’s the site of Fort Standish , a turn-of-the-century series of gun emplacements that have been left to nature (unlike their counterpart, Fort Warren , on George’s Island ). You can take one of the trails on the island to hike past these historic sites and do a little urban exploration of the fort.

In addition to its history, Lovell’s Island has a few backcountry campsites (book one here ), each with their own composting toilets. However, there’s no drinking water available on the island, so be sure to bring enough for your stay.

Rainsford Island doesn’t have too much to offer, as it’s only 11 acres, and half of it has very little tree cover. However, there’s some interesting history to be explored; just open the mailbox at the central beach to find historical reading materials and old photos.

The island served as a quarantine hospital and a boy’s reform school from the early 1700s until 1925. Unlike on the other islands, though, only the foundations of these buildings remain.

There are no ferry connections to Rainsford Island, and it’s now used mostly by boat owners who want to escape the crowds of the other islands. But the large beach firepit and improvised seating around it suggest it’s a common party spot.

Peddocks Island is one of the largest in the harbor and possibly the most interesting, both for its historical significance and its camping and hiking options. The island’s most striking feature is Fort Andrews, a military facility build in the early 20th century to guard the harbor and house prisoners of war during both world wars.

Although some of Fort Andrew’s buildings are still standing, most have been boarded up and are closed to the public. However, negotiations are underway to restore the buildings that have the most potential for tourism.

Hidden among the military facilities on Peddocks Island is a series of yurts that can house up to six campers ($55/night for MA residents, $60 for non-residents). These yurts are in high demand, though, so reserve them as early as possible.

Following the trails out to the eastern part of the island leads to a series of summer cottages that have been used by vacationers from Boston and, before that, by Portuguese fisherman. While some are occupied, others have fallen into disrepair and are slated for demolition if owners cannot strike a deal with the state .

Those familiar with the Boston Harbor may have noticed that I’ve left off George’s Island, the most popular destination in the harbor. Given the amount of tourism on the island, it would be better to visit using the ferry system, and information on what to do there is readily available from the Boston Harbor Islands website .

The outer harbor lies beyond the protective guard of the Deer Island and Hull peninsulas, so the water is quite a bit rougher, which also means it has less going on in terms of maritime history.

Another issue? The birds that make their home on the outer islands can be very aggressive during their nesting season (April-August), particularly on Green Island and Calf Island .

When I paddled near Green Island, my kayak was dive-bombed by a flock of birds that were not happy I was there. Disembarking onto the islands is strongly discouraged by wildlife officials – for the protection of both the birds and the visitors.

Despite all of this, a few points of interest still make visiting the outer harbor worthwhile. The 100-foot-tall hill on Greater Brewster Island boasts some of the best views of the harbor region, and Little Brewster Island is home to Boston Light, the oldest continually lit lighthouse in the U.S (dating back to 1716). Access is restricted, but tours of the lighthouse and the island can be arranged .

The final stop on a tour of the harbor islands is Graves, home to the Graves Lighthouse . Graves is more of a collection of rocks jutting out of the ocean than an actual island, making the lighthouse an even more spectacular sight.

The lighthouse was auctioned off in 2013 and bought by a Boston-area family, who’s spending a fortune restoring it . As of now, it’s closed to the public, and it’s extremely unsafe to approach the rocky outcroppings around the lighthouse. But, it will hopefully open to visitors sometime in the future.

Kayaking Boston Harbor is a fun way to get that away-from-it-all feeling without having to go all that far. I should emphasize again that it’s only appropriate for people with sea kayaking experience – but if that’s you, it’s a must-do adventure in Boston .

Have you been kayaking in Boston Harbor? Tell us about it in the comments!

About Ryan Victor

Born and raised in Montana, Ryan Victor is a lover of the outdoors and a passionate hiker, kayaker, and skier. After he and Jen got married in 2016, they quickly got rid of all their stuff and left their jobs in Boston to fulfill their dream of traveling the world. Now, they travel together (and occasionally separately) while working remotely, and housesit in many of the places they go. Ryan’s visited 20 countries, and his travel style revolves around getting far off the beaten path and finding adventure wherever possible.

May 10, 2018 at 9:16 am

Can you paddle to the camp sites or is it a long portage?

May 11, 2018 at 6:02 am

Most of the campsites are fairly close to the shore, the exception being those on Peddock’s Island, which can be anywhere between 1/3 and 1/2 miles from it with a decent amount of elevation gain. Grape Island has some of the easiest access. The maps on the reservation site are fairly helpful https://www.reserveamerica.com/camping/boston-harbor-islands-sp/r/campgroundDetails.do?contractCode=MA&parkId=32603#sr_a .

May 27, 2016 at 11:24 pm

Thank you for this beautiful post!

June 5, 2016 at 11:29 am

Thanks so much for reading Anka, I’m glad you liked it!

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Boston Harbor Islands + Skyline Tour 

Check Booking Availability

Price includes:

• Extended Helicopter Tour of Boston Harbor Islands + Boston Tour 
• Comprehensive Boston City Tour showcasing iconic landmarks
• Opportunity for photos throughout the flights
• Complimentary snacks, beverages, and coffee in our lounge
• Personalized helicopter experience with a skilled pilot and guided city tour

Enhance your experience (during checkout):

• Private helicopter tour for a more intimate experience
• Gift box for her, adding a touch of luxury and thoughtfulness
• Gift box for him, tailored to his tastes and preferences
• Go-Pro Video Add-On to capture your incredible flights
• VIP Luxury Experience, where every detail is taken care of

During your tour

Relax in our lounge.

Frequently asked questions

What is your cancellation policy, what if there is inclement weather, is there an age restriction, is there parking at your location, related tours.

Sunset Tour

25 – 30 minute tour $499 per person

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125 Access Rd Norwood, MA 02062

To Do Today: Visit Boston Harbor Islands

Take a short ferry ride to discover history, wildlife, and nature

Little Brewster Island is the home of Boston Light, the oldest continually used light station in the country. Photo by Bill Gormley

Shana Singh (COM’23)

Boston Harbor Islands , accessible by ferry

Ferry tours depart Boston at 10 am, 12 noon, and 2 pm to Georges Island, and 10:30 am, 12:30 pm, and 2:30 pm to Spectacle Island. Check out the return schedule here .

Boats depart from Long Wharf North, 66 Long Wharf, Boston (next to Christopher Columbus Waterfront Park).

Round-trip ferry tickets are $24.95 for adults, $22.95 for students, military, and seniors (65-plus), $17.95 for children (3 to 11), and free for children under 3.

Why should I go?

The Boston Harbor Islands are a collection of 34 islands and peninsulas located within Boston Harbor. Those who visit the area will discover the nature and history that played an important role in the development of Boston and beyond. Considered both a national and a state park, the Harbor Islands attract over half a million visitors each year. The park’s islands offer wildlife sanctuaries, parks, and historic sites like Fort Warren, Fort Andrews, Boston Light, and Deer Island.

Home to the Civil War–era Fort Warren, Georges Island is a must-see for history enthusiasts. The fort, made of stone and granite, was built between 1833 and 1860 and used for coastal defense following the start of the American Civil War. It eventually became a training facility for Union soldiers and later served as a prison for Confederate soldiers and government officials. Visitors can tour the fort’s bakery, parade ground, and pitch-dark tunnel and and hear about the legend of the fort’s rumored ghost, the Lady in Black. End your day at Georges Island with a picnic.

Spectacle Island is ideal for swimming, boating, and hiking. The 114-acre island offers panoramic views of Boston Harbor and has a beach, perfect for relaxing by the sea. Over the years, the island has supported farming and even housed resort hotels before becoming a public park. On select dates, Spectacle Island offers jazz concerts and visitors can grab a bite at the snack cart before concluding their day. 

The Boston Harbor Islands also offer a special three-hour narrated cruise on select dates to explore three lighthouses: Long Island Head Light, Graves Light, and Boston Light (America’s first and oldest continually used light station). Learn about maritime history while enjoying views of the Harbor Islands and Boston skyline. Check out available dates and prices here .

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Boston Light Lighthouse Tours

Lighthouse Tours of Boston Harbor

Experience the historic lighthouses of boston harbor on our special two-hour narrated cruise.

Voyage through maritime history with a special three-lighthouse tour featuring close-up views of Long Island Light, Graves Light, and Boston Light – America’s first light station.

Delve into history as you travel to the edge of Boston Harbor on an exciting 2-hour cruise and encounter three iconic lighthouses, and enjoy onboard narration provided by Boston Harbor Islands park staff and volunteers from the United States Coast Guard. Learn about the maritime traditions of Boston Harbor, enjoy unforgettable views of the park and city, and experience one of the most unique and historically significant ports in the country.

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10 Top Boston Harbor Cruises

Venture on the water to explore Beantown's waterfront, maritime history and more.

Courtesy of City Cruises by Hornblower

Take in stunning city views from the water.

Boston is the most populous city in New England – and for good reason. This Massachusetts metropolis may host modern shopping, dining and cultural attractions, but Boston is built upon a rich American tapestry created over the centuries that's still visible in its quaint neighborhood streets and stone houses. The city's historic harbor along the Massachusetts Bay set the scene for a significant portion of Boston's story; once the site of Revolution-era protests like the Boston Tea Party, this body of water is now primarily used for revelry. No visit to Massachusetts' capital city would be complete without some time on Boston Harbor.

If you're planning to spend some time in Beantown during the warmer months, consider boarding a schooner for an hour or two of sightseeing, or head out on a boat you can pedal or sail yourself. Cruises on the harbor offer a range of historical tours, romantic dinners on the water, unique brunches with friends or even the chance to spot some endangered whales. Whether you opt for a tall ship or a smaller, more eco-friendly vessel, soak in city views and enjoy your time on the water with the following top Boston Harbor cruises.

Boston Harbor City Cruises by Hornblower

Hornblower's City Experiences brand offers a wide variety of land-based and on-the-water tours, which includes City Cruises. While the brand has greatly expanded over the past century to 125 U.S. cities and more than 100 countries, it all began with Boston Harbor Cruises, founded in 1926.

Today, Boston Harbor City Cruises encompass a range of ways to see the city from the water. You can book a brunch, lunch or dinner cruise on a dining vessel like the 600-passenger Boston Odyssey; time your sailing for sunset; or plan a big outing for a holiday such as the Fourth of July. Dare to ride Codzilla, a thrilling speed boat designed to leave slow-paced sightseeing tours in its wake. Zoom around the harbor for around 45 minutes at up to 40 miles per hour – and since you likely will get wet, ponchos are available on board. This 70-foot harbor boat, complete with a toothy paint job, also boasts an original soundtrack.

If you're looking for a different kind of enjoyment with a little less aquatic adrenaline, Boston Harbor City Cruises partners with the New England Aquarium for a series of spectacular whale watching trips. From Boston's Central Wharf, you'll head to Stellwagen Bank National Marine Sanctuary, one of the world's most active marine sanctuaries. Whales in the region include humpbacks, minke whales, the endangered right whales and more. You can also try to spot sea birds, dolphins and other marine life – but if you don't see whales on your cruise, a free ticket will be offered to you for a future whale watching trip.

See more of Boston: Things to Do | Hotels

Classic Harbor Line Boston

Courtesy of Classic Harbor Line Boston

With a fleet that includes schooner Adirondack III and motor yacht Northern Lights, Classic Harbor Line is a great choice for a Boston Harbor cruise. Join a guided sightseeing tour or charter your own yacht for the day; the schooner is designed for 40 people or less, while the motor yacht can accommodate just under 150 guests. Classic Harbor Line offers themed cruises, if your interest is piqued by either an adults-only nighttime City Lights sailing (perfect for couples) or a cruise that pairs a day of harbor islands and lighthouses – including the country's oldest – with a picnic lunch. The two-hour sunset cruise aboard Northern Lights is accompanied by the nightly cannon fire from the USS Constitution , also known as "Old Ironsides" – the world's oldest commissioned warship still afloat, built in 1794.

If you want to sail Boston Harbor with a cold beer, you can't go wrong with Sails & Ales, a special themed cruise created in partnership with the local favorite Harpoon Brewery. Sail along the waterfront at sunset past sights like Independence Fort as your Harpoon representative explains beermaking techniques. You'll sip four flagship or seasonal beers plus one cider. A ticket for a future free tour of the brewery is included, and you'll know exactly where it is because this cruise sails right past it.

Boston Green Cruises

Right on Rowes Wharf behind the Boston Harbor Hotel, Boston Green Cruises has a fleet of three vessels: the 350-passenger Sir Winston and two low-emissions boats known as Beach Cat, a 44-foot catamaran that seats 30 people, and Zulu. Boston Green Cruises, which calls itself Boston Harbor's first eco-friendly fleet, offers a 60-minute, fully narrated sightseeing tour for all ages that covers the city's marquee waterfront sights. A 90-minute sightseeing cruise is also on offer on one of the company's smaller ships and includes time passing the historic locks along the Charles River. If you're looking for the ultimate intimate Boston Harbor cruise, consider a private charter, which can run anywhere from two to eight hours. Be aware that in the event of inclement weather, cruises will be rescheduled but not refunded, per company policy. Past Boston Green Cruise participants have said the captain they sailed with was friendly and knowledgeable, providing a great history lesson on the harbor.

Massachusetts Bay Lines

Courtesy of Massachusetts Bay Lines

Massachusetts Bay Lines, referred to locally as Mass Bay Lines, offers sightseeing tours and private charters in Boston Harbor – but also floating concerts and DJ sets you can experience with up to 379 of your closest new friends. Beyond traditional sightseeing tours and music cruises, Mass Bay also hosts a handful of themed options. Once per month from May through October, you can take part in a two-hour Full Moon Cruise, which sets sail under the lunar light of a full moon and the city lights of Boston in the background. Passengers 21 and up may choose to celebrate New Year's Eve or Independence Day by cruising in the city known as the birthplace of the American Revolution: The adults-only sailings on Dec. 31, July 3 and July 4 mark the occasions with a cash bar, dancing and a prime place to watch the fireworks. Dog owners will be happy to know Mass Bay even welcomes one four-legged friend per each adult ticket on its Dog Days of Summer sailings – but you're not required to bring a pooch, so if you're simply a dog lover looking to see the sights, head down to Rowes Wharf.

Cycleboat Boston

Courtesy of Cycleboat Boston

If you've walked around Beantown but still want to get some steps in – even on the water – consider booking a sightseeing harbor cruise that you can pedal. Cycleboat Boston lets you ride on bike seats and cycle your way through Boston Harbor to help propel the boat, but it's not required if you'd rather relax in the lounge. Tours focused on U.S. history cover the Boston Tea Party Ships , Bunker Hill Monument and the Charlestown Navy Yard, among other local sites. Pedal along during the day, by night or at sunset; the morning cruises encourage mimosas, but you must provide valid ID and bring your own beverages (with coolers and ice provided). Recent reviews rave about the captain and first mate and say if you're not looking for much of a workout you can just sit back and have fun.

Liberty Fleet of Tall Ships

Courtesy of Liberty Fleet of Tall Ships

Board a schooner from the Liberty Fleet of Tall Ships and sail Boston's historic harbor in fitting style. Your two-hour tour begins by embarking the 125-foot Liberty Clipper at Long Wharf, or you can opt for a more intimate, 90-minute experience on the Liberty Star, which is less than half the size of the Liberty Clipper. Tickets and drink tickets can be purchased ahead online or during your cruise; otherwise, you can bring your own snacks and bag lunches.

The fleet sails Boston Harbor from June through September, offering sunset cruises, history sailings and evening cocktail cruises where the rum never stops flowing (with group discounts available for parties of four). Sailing enthusiasts may want to join the Sail Through Time Cruise, which documents the history of some of Boston's most famous sailing ships, as well as the people who lived and worked on them; you can enjoy this fact-filled day on the water with a docent from Boston by Foot as your guide and even help hoist the sails. Passengers appreciate the serenity of seeing the city from a new perspective.

Boston Electric Boats

@urbanophoto | Courtesy of Boston Electric Boats

India Wharf was one of the largest commercial wharves in the Port of Boston during the 19th century, and today the India Wharf Marina, just a short walk from the aquarium, hosts boats for rental or charter through Boston Electric Boats. Those seeking a self-guided Boston Harbor cruise will be pleased to take advantage of the Be Your Own Captain Rental, available for two hours at a time. No experience or boating license is necessary to pilot the boat – though the company will make sure you're comfortable before you set off – and up to 11 people can sail along with you.

If you'd rather leave the steering to someone else, a Captain Provided Charter accommodates up to six passengers, allowing you to take in the breeze and enjoy any refreshments you may have brought. The boat's canopy provides shade, while the open deck is perfect for basking in the sun; the enclosure windows can be opened or closed to adjust for the weather. These electric boats are more eco-friendly with no fuel odors and a quiet motor. Boaters have commented that preset GPS routes make piloting the boats much easier, and a top speed of 6 miles per hour keeps the ride safe and relaxing.

Boston Harbor Islands Ferry

Beginning in May, a ferry service provided by Boston Harbor City Cruises connects downtown Boston to the Boston Harbor Islands. This transport gives a unique chance to experience some of the wilder elements of Boston's seaways, with ferries that run to Spectacle Island, Georges Island and Thompson Island during the warmer months.

On Thompson Island, accessible only on weekends, you'll get a brief orientation to start your visit; on Saturdays, a National Park Service ranger hosts a guided walk to explore the island ecosystems, including salt marsh, beaches, meadows and forest. Spectacle Island is a 114-acre island perfect for a day of hiking and swimming, with an accessible lifeguarded beach and occasional weekend jazz concerts. Georges Island offers up the history, as it houses the Civil War-era Fort Warren; ranger-led tours are available.

Charles Riverboat Company

The Charles Riverboat Company was founded in 1990 and remains a family-run business whose five vessels now carry more than 50,000 passengers per year. The company believes that whether you're a visitor or a local, seeing the city from the water is a spectacular experience that all will enjoy. Guided historic sightseeing cruises feature Harvard University, modern skyscrapers like the Prudential Building and more. Learn about the architecture and building design of landmarks along the harbor and Charles River on the two-hour Architecture Cruise.

As you might expect, many of the Charles Riverboat offerings focus on its namesake river, which flows into Boston Harbor, whether you want to see fall foliage, hear haunted tales or simply enjoy a cocktail at sunset with live music on the Charles River. The company also has a booming charter business for graduations, engagements, retirements and other special celebrations, with recent customers citing extraordinary service from staff.

Boston Duck Tours

If you can't choose between tours on land and boat, you don't have to. It's nearly impossible to visit Boston and not run into one of its renowned duck tours. This type of amphibious automobile was originally created as a military vehicle under the code name "DUKW," and now these boat-bus hybrids can transport tourists in and out of the water. To cap off your city visit, venture slightly beyond Boston Harbor with this cruise along the Charles River.

The vehicles used today by Boston Duck Tours are uniquely designed to roll past city sights like Boston Common , the Old North Church and the Fanueil Hall Marketplace before or after launching into the Charles River for views of the Cambridge and Boston skylines. This Boston boat experience is unlike any other, led by beloved "conDUCKtor" guides: You might meet Duck Tracy, Florence Waters or Professor Quackenstein, who will regale you with their own take on Boston's top attractions. A lighthearted but thorough excursion through city history, Boston Duck Tours has won many accolades. Past customers remember these unique tours as one of the best parts of their visit – and as a special draw for kids, the tour guides may allow children to briefly steer the boat in the water for a particularly memorable experience.

You might also be interested in:

• The Best Boston Tours
• The Top Things to Do in Rhode Island
• The Top River Cruise Lines
• The Top Statue of Liberty Cruises
• The Top NYC Dinner Cruises

Tags: Travel , New England Vacations , US Vacations , Cruises

World's Best Places To Visit

• # 1 South Island, New Zealand
• # 4 Bora Bora

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• Georges Island
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• Bumpkin Island
• Little Brewster Island
• Cathleen Stone Island
• Other Islands
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• Fort Warren
• Fort Andrews
• Boston Light
• About the Park
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Behind the Scenes with Seasonal Rangers

June 4, 2024

Guess who’s back? Our seasonal rangers! We are all eager and ready to welcome visitors to the Boston Harbor Islands National and State Park. This month has flown by as we have been training and working hard to prepare for the 2024 season.   

Training on The Boston Harbor Islands  

As part of our training, we visited several islands, including Spectacle, Georges, and Peddocks Islands. On our first day of island training, park rangers from both the Massachusetts Department of Conservation and Recreation and the National Park Service set sail for Spectacle Island. That first day of island training may have been rainy, but it sure didn’t dampen our spirits!  Returning rangers, were excited to come back to the islands after six months. For new rangers, they took their first step on the islands.   

Rangers get a rainy tour of Spectacle Island. | CREDIT: NPS Photo/ A. Benstead]

Spectacle Island looked as lush and green as ever. The North Drumlin greeted us as it continues to proudly stand as the highest point in the harbor. Later that day, the rain stopped, and one returning seasonal ranger led us on a small hike to the island’s “saddle” to give us an overview of the history of Spectacle Island.  

On a beautiful, sunny day later that week, we set sail again, but this time to Georges Island. We went through the inner harbor and the Narrows until we saw the great, granite walls of Fort Warren that once protected Boston. From there, we had a few returning seasonal rangers guide us through the history of Fort Warren. We even went to the Dark Arch to pay a little visit to the Lady in Black!  

For the final day of island training, we visited Peddocks Island to go over operations for the season. To end our training on the islands, we sailed through the outer harbor to catch a glimpse of the outer islands and to see Boston Light and Graves Light from a closer distance.  

Rangers take a cruise of the Outer Harbor, including a visit to Boston Light. | CREDIT: NPS Photo/ A. Benstead]

On our final day of training, we prepared the Welcome Center for the season. We restocked essential supplies, including Junior Ranger booklets, badges, stickers, and most importantly, maps! After we set everything up, we kept the Welcome Center open for a couple of hours to tell visitors about Free Ferry Weekend and all the exciting programs and events we have planned for the season.  

Saturday was the first day of Free Ferry weekend and despite some rain, we had a large line of visitors eager to get tickets. All weekend, Georges Island was bustling with happy visitors who were able to take tours and explore Fort Warren.   

We are all happy to be back with a successful start to the season. Stay tuned for what else we have in store for you this summer!  

Boston Light george's island NPS Park Ranger Spectacle Island

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Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary

I f you’re here, that means you’re probably planning an epic New England road trip along the coast, and man, I’m SO excited for you! Hi, my name is Sam, and I’ve been exploring this corner of the world for over 10 years now. I’ve taken countless road trips along the coast, and I’ve finally perfected my unforgettable Boston to Bar Harbor, Maine itinerary for those looking to explore the  New England coast .

To date, this is my favorite road trip I’ve done, and I can’t wait for you to experience it for yourself. To help you plan the perfect adventure, I’m going to share all my expertise on this area with you, offer my best tips for planning your trip, and give you my ultimate itinerary that was years in the making.

While following along, I encourage you to tailor this itinerary to your own preferences depending on how much time you have for your trip, but I do make suggestions on how long it takes to make the drive, and see all the best places on the way.

Are you ready to start planning together? Let’s go!

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

Road Tripping From Boston To Bar Harbor – The Basics

Before we jump into the itinerary, let’s get started with some questions you may have …

How Long Is The Drive From Boston To Bar Harbor?

If you don’t make any stops at all, and take the most direct route, the drive takes between 4 hours and 40 minutes to 5 hours, and spans about 280 miles. It could be longer depending on traffic getting out of Boston. If you happen to leave Boston during rush hour, definitely expect it to take a bit longer.

However, if taking a road trip, you could really make this drive as long as you wanted because there are so many amazing things to see along the way, and some fun detours to take. In just a sec, I’ll give you my suggestions on how long you need to make this trip and see as much of the coast as you can 😉

The auto road to the Cadillac Mountain Summit in Acadia National Park.

Is The Drive Scenic?

I think so, yes! But it kind of depends on your expectations.

While many parts of the actual drive are on highways that are kind of boring, there are  so  many great places to stop along the way that can make the drive very scenic.  Especially  if you take some of my suggested detours and scenic byways! But is every second of the drive stunning? Well, no. So it’s good to set expectations. It’s really more about the stops you make during the trip than the actual drive itself.

There are some portions of the actual drive that are very beautiful, though.

How Many Days Do You Need To Drive From Boston To Bar Harbor?

Since there are just tons of incredible things to see, I’m recommending one week, or 7-8 days, as I know that this is how much most people have to make this drive. If you have longer than a week, then I say it’s worth it to enjoy going at a slower pace. But you can definitely enjoy the top things to see in a week. This will also include two days in  Acadia National Park!  For my itinerary, I’m mapping out 8 incredible days for you, and you can adjust it to fit your schedule 😊

Best Time Of Year To Drive Boston To Bar Harbor

Generally,  June-September  is the best time to drive from Boston to Bar Harbor, as this is when you can expect the  best weather, and longest days .  July and August is considered peak season  along the New England coastline, so this is also when you can anticipate the most crowds and highest hotel prices. But gosh, it’s so worth it!

However, I’ve done this road trip in all seasons – yep, in spring, summer, fall, and even winter! As a second suggestion, I love  May to avoid some of the crowds  and still enjoy mild weather, and also  October to chase all the stunning fall foliage .

I’m going to give you some suggestions later in the post to turn this drive into a fall foliage adventure, so be sure to check that out if you’re planning your trip in the fall season 🍁😉

It’s also good to know that some places along the New England coast are seasonal, especially seafood shacks, boat tours, and ice cream places. If they’re seasonal businesses, it’s likely they won’t open until late May or June and begin to close down around Labor Day or only stay open possibly mid-October. But you’ll always be able to find places that are open year-round, too.

How Many Days Should You Spend In Acadia National Park?

Speaking of Acadia, that’s probably the reason you’re making this drive, right? This park is undoubtedly the top attraction in New England, and rightfully so. I always recommend a minimum of two days to explore, allowing 1 full day in the park, and then at least a half day to see Bar Harbor, which is such a charming town along the coast.

If you have more than a week for this trip, you could definitely add an extra day to Bar Harbor so you have two full days to explore the park.

Is There A Ferry From Boston To Bar Harbor?

No, there is no ferry that goes between Boston and Bar Harbor. The best way to make the trip is to drive.

The only ferry to Bar Harbor is the one from Nova Scotia, which is the CAT Ferry.

Is It Worth Going All The Way To Bar Harbor?

Oh yes! I often get asked this because Bar Harbor is pretty far up the Maine coast, and it’s one of the top attractions most out of the way in New England. But yes, it’s absolutely worth the drive. Because there are so many great things to see along the way, and since Acadia offers some of the best and most iconic coastline views in the Northeast, it’s very much worth the effort.

Overview: Best Stops To Make When Driving Boston To Bar Harbor

These are the top places I recommend stopping in that I think are very much worth your time. Some of them require a bit of a detour, but depending on your preferences, you’ll probably be happy you went out of your way!

→  Massachusetts North Shore : This includes Marblehead, Salem, Gloucester, Rockport, Ipswich, and Newburyport. I suggest you drive the Essex Scenic Coastal Byway on your way to or from Bar Harbor to see some of these towns, depending on which appeals to you the most. I have a slight preference for Salem, Marblehead, and Rockport, which are all small and easy to do in a couple of hours each. I’ll go more into this later in the post 😉

→  Portsmouth, New Hampshire : Pretty much just off I-95 and not out of the way at all, Portsmouth is a charming coastal city that feels more like a quaint town. Great historic New England scenery and shopping! I recommend this stop if you’re looking for more of a town vibe vs. coastline, as the coastal views here aren’t as impressive as the rest of the places on this list.

→  Southern Maine Coast : This includes places like York & Cape Neddick, Kennebunkport, and Ogunquit. I usually suggest stopping at Nubble Lighthouse in York, spending a couple of hours each in Kennebunkport and Ogunquit, and even staying the night in one of these two towns.

→  Portland, Maine : The state’s largest city is filled with lots of maritime charm, amazing dining, lighthouses, and history. If you like cities, this may be worth staying a night, but you can also see the highlights in a few hours if you’re not a city person.

→  Freeport, Maine : Home to the flagship L.L. Bean store! It’s not worth it for everyone to stop, but gosh, it’s a pretty cool place to see if you’re looking to pick-up some New England clothing and accessories.

→  Maine’s Midcoast : Between Freeport and Belfast, just before getting to Bar Harbor, there are lots of great towns along the coast to explore in this region, including Harpswell, Boothbay Harbor, Wiscasset, Rockland, and Camden. I have so many suggestions for hidden gems and places to visit along this portion of the drive, which I’ll go more into during the itinerary portion of the post!

The PERFECT Boston To Bar Harbor, Maine Road Trip Itinerary

Overview of this itinerary:.

Since most people reading this will need to start and end their trip in Boston to catch a flight, that’s how I’m formatting the itinerary. You’ll be making most stops on the way to Bar Harbor, but also saving a few for the drive back so you have something to look forward to 😉

Day 1 : Explore Boston.

Day 2 : Get an early start and drive to either Kennebunkport or Ogunquit. Spend 1 night.

Day 3 : Drive to Portland to explore for a few hours, and then make your way to Camden with a few optional detours for lighthouses and great coastal scenery! End in Camden to spend the night.

Day 4 : Spend the morning in Camden, and then drive to Bar Harbor. Enjoy downtown Bar Harbor and grab dinner. Spend two nights here.

Day 5 : Explore Acadia National Park during the day, and more of Bar Harbor at night.

Day 6 : Drive to Boothbay Harbor to spend 1 night. Take a boat tour.

Day 7 : Drive to Portsmouth and spend a few hours enjoying the shops, and drive the Essex Scenic Byway along the Massachusetts North Shore to make your way toward Boston. Stay the night in this area.

Day 8 : Arrive back in Boston to head home.

Day 1: Explore Boston

Boston is the perfect starting point for most New England itineraries, but it’s also one of the top places to explore in the region, so you should definitely plan at least a full day in the city!

Rooted in history, packed with New England charm, and filled with exciting dining and cool things to do, you can actually cover a lot of ground in just a day in Boston, including the top highlights.

Here are some of the top things I suggest first-timers do :

→ Take a food tour to get a taste of what this region is all about. I have a detailed guide on all the  best Boston food tours  to help you pick the best one! But seafood and Italian cuisine are especially great here.

→  Visit the most charming neighborhoods , which are  Beacon Hill  and the  North End . The North End is also where you’ll find the best Italian restaurants.

→ Stroll through the  Public Gardens  and  Boston Common . The Boston Public Garden was the very first in the U.S., and it’s so beautiful and photogenic 😍 Boston Common isn’t as scenic as the Public Garden, but in the fall during foliage season, it’s on fire with color. Plus, they’re both really close to one another.

→ If you’re looking to do some  shopping , head to  Newbury Street  and  Copley Place .

→ Visit the  New England Aquarium .

→ Explore parts (or all!) of the  Freedom Trail , which is a walking tour that takes you to historically significant places around Boston. You can also take  this awesome Freedom Trail tour .

→ Grab lunch or coffee at the beautiful and Instagram-worthy  Tatte Bakery , which has locations around the city (you’ll see why I recommend it when you walk in 😉).

→ End your day with a nice dinner out. I love  Neptune Oyster , but they don’t take reservations, and it can be a long wait time. If that’s not worth it for you, I also love the  Union Oyster House  for a traditional New England dining experience. But there are so many fantastic places in Boston to choose from.

How To Get Around Boston :

Boston is very walkable, and most of the tourist attractions, which are truly the top things to see in the city, are within walking distance to one another (less than a mile) in the downtown area. If you’re exploring for a day, you likely won’t need to use public transit, but may want to get an Uber or Lyft, which are widely available, just to save time (or if you’re tired!).

Where To Stay In Boston :

All of these suggestions are in great locations, and within walking distance to most everything!

→  Boston Harbor Hotel

→  Revere Hotel Boston Common

→  The Godfrey

Day 2: Drive To Southern Maine

First thing’s first, you’ll want to  pick-up your rental car in Boston  early in the morning. Then, head out to start your drive to southern Maine! During this part of the trip, you’ll pass through Portsmouth, New Hampshire, but don’t worry, we’re going to stop there on the way back 😉 To get to southern Maine, you’ll hop on I-95.

So, Ogunquit or Kennebunkport ?  Well, you can do both if you want! Ogunquit is about 25 minutes south of Kennebunkport, and the biggest difference, as mentioned, is that Ogunquit is more of a beach town, whereas Kennebunkport is more of a coastal town. That said, Kennebunkport also has beaches, and Ogunquit is also just as charming – I honestly love both.

Since you’ll pass by Ogunquit on your way to Kennebunkport, you can stop by for a few hours and see the beach, and the cute little town, and then end in Kennebunkport. You’ll want to decide which town to spend the night in – both have plenty of hotels and dining options.

On your way to Ogunquit and Kennebunkport, I also recommend you stop in York , which is just south of Ogunquit.

Notable stops to make in York if you have time :

• Nubble Lighthouse on Cape Neddick  – the lighthouse itself is not accessible, as it’s on its own little island, but the viewpoint is really great and worth a stop! It only takes a few minutes.
• Stonewall Kitchen Flagship Store & Café  – This New England brand started in Maine, and is now sold in specialty stores all over the country, but the flagship store has everything, and is really fun! The café is also very good, and a lot of people come here for lunch.
• Downtown York  – Waterfront scenery, and some cute shops.
• The York Cliff Walk  – A pedestrian path along the coast with beautiful views.

*If you’re short on time , I would just do Nubble Lighthouse and maybe Stonewall Kitchen, but if you have time, I do recommend the other two stops.

Marginal Way in Ogunquit, Maine.

Best Things To See In Ogunquit In A Day :

→  The charming downtown  is filled with shops and eateries.

→  Ogunquit Beach , which is one of the best beaches in Maine!

→  Marginal Way , which is a pedestrian walking path along the coastline that connects downtown Ogunquit with the cute Perkins Cove Harbor.  This is my personal favorite thing to do in Ogunquit.  The trail is easily accessible from downtown, and is just over 1 mile long each way.

→  Perkins Cove  – Once you arrive there after walking Marginal Way, there are some really cute shops to explore, and a lovely bridge that makes for fun photos.

Ogunquit Beach Lobster House Restaurant.

Where To Eat In Ogunquit :

• Ogunquit Beach Lobster House
• Footbridge Lobster in Perkins Cove for a lobster roll!
• BeachFire Bar & Grille

Psst!  I have an entire guide on  things to do in Ogunquit , if you’re looking for more ideas!

Kennebunkport, Maine.

Best Things To See In Kennebunkport In A Day :

→  The adorable downtown , which is mainly Dock Square. You’ll find colorful storefronts and great restaurants here.

→  Drive to Cape Porpoise , where you’ll find beautiful coastal New England scenery, and the cute  Farm + Table shop .

→ Enjoy the views of the cove from  Kennebunkport Bridge  (right at Dock Square).

→ Take a coastal walk on  Parsons Way .

→ If you have time, head out on a  lobster tour with Rugosa .

Where To Eat In Kennebunkport :

• Allison’s Restaurant for a great casual meal
• Cape Porpoise Lobster Co. for a lobster roll!
• Old Vines Wine Bar

Day 3: Drive To Portland & Make Your Way To Camden

Portland Head Lighthouse.

This day ends in the beautiful coastal town of Camden, but you’ll be making some fun stops along the way! You can make this day easy by just driving to Portland, and then driving straight to Camden, or you can make it longer and more adventurous by making as many stops you as you feel like. Take a look at all my suggestions, and plan according to your preferences 😊

Option to add a night in Portland : The reason I have you scheduled to only stop in Portland for the day is because it’s  such  a short drive from Kennebunkport and Ogunquit, and personally, I think the scenery around the Camden area is more quintessential Maine. However, if you have extra time, you can definitely stay the night in Portland, and continue on to Camden the next day!

Things To Do In Portland In A Few Hours:

→  Take a food tour!  Portland is a huge foodie destination, and this is a great way to taste your way through the city.  The Old Port Seafood Lovers Tour , and  Old Port Culinary Walking Tour  are both great options.

→  Visit the lighthouses.  If you only have time for one, definitely make it  Portland Head Lighthouse . This is probably the most iconic lighthouse in New England, and it’s absolutely beautiful. Nearby are also  Spring Point Ledge Light , and  Bug Light , which are smaller, but still fun to visit. These are all in South Portland, so you’ll want to see them first before getting to downtown Portland.

Old Port in Portland.

→  Stroll around Old Port . I suggest parking somewhere around Commercial Street, and then walking around from there. This is the most unique and charming part of the city along the waterfront. Exchange Street and the streets nearby are nice shopping areas, too.

Optional Stops That Are Worth Your Time On The Way To Camden :

Some of these will definitely add time to your trip, so map them out carefully based on your plans to ensure you have enough time in your day.

Marshall Point Lighthouse.

→  Freeport  to shop at the L.L. Bean Flagship Campus.

→  Wiscasset  – a charming little town with a famous seafood stand called Reds Eats. Also known as being the prettiest village in Maine. You’ll drive right through it on your way to Camden.

→  Pemaquid Lighthouse  – a beautiful lighthouse surrounded by dramatic coastline and parks. There is a small fee to enter the grounds, and it’s cash only.

→  Moody’s Diner in Waldsboro  is right on your way on the righthand side, making it  a little too easy  to swing in for one of their famous whoopie pies! It even made my list of the  best whoopie pies in Maine .

→  Marshall Point Lighthouse  in Port Clyde. This famous lighthouse was featured in the movie  Forrest Gump , and it’s such a beautiful area to visit. This is the lighthouse in my homepage photo!

→  Owls Head  is a small town that’s not too far of a detour, and is home to Owls Head Lighthouse, and some beautiful coastal scenery. This is one of my top, most favorite lighthouses in New England.

→  Rockland  is a charming little coastal town with a great Main Street for shopping. Also home to Rockland Breakwater Lighthouse.

Note s:  You’ll pass by Boothbay Harbor on this portion of the drive, but don’t worry! You’ll be stopping there for a night on the way back  😉  You can also make some of these stops on Day 6 of this itinerary when you drive from Bar Harbor to Boothbay Harbor .

You’ll want to arrive in Camden around dinnertime, so you can get settled into your hotel, and then explore the town a bit before sunset.

Camden, Maine.

Best Things To Do In Camden:

→  Head out on a sunset windjammer tour!

→  Walk around the harbor  to enjoy the idyllic waterfront scenery. Also walk over to the Bay Road Overlook (comes up in Google Maps) for the perfect view of the harbor backdropped by the mountains.

→  Grab dinner at a fabulous restaurant . Some of my favorites are Natalie’s, The Waterfront (yep, that’s the name 😊), and Franny’s Bistro.

→  Get some ice cream for dessert  at River Ducks or Camden Cone.

→  Drive the auto road  in  Camden Hills State Park  to the top of Mt. Battie and enjoy the bird’s-eye views of the harbor. This road is only open seasonally, but usually only closed in the winter.

→  Shop the lovely boutiques  on Main Street and Bay View.

Day 4: Spend The Morning In Camden & Then Drive To Bar Harbor

Refer to the section above for ideas on things to do in Camden the next day. If you weren’t able to take a sailing tour the night before, I do highly suggest booking one for the next day before you leave – this is one of the best places in Maine for a sailing tour!

⛵︎ Here is the Camden sailing tour I recommend:

Windjammer Classic Day Sail

Then, make the drive directly to Bar Harbor. On the way, you’ll cross the  Penobscot Narrows Bridge , which is one of only four bridge observatories in the entire world! If you have time, it’s worth a stop to enjoy the views from the observatory.  Click here for information and fees for exploring the bridge . But it is completely free to drive over if you’re just passing by.

Things To Do Your First Night In Bar Harbor:

→  Walk around the adorable town .

→  Enjoy sunset from Shore Path right in town , with is a coastal walkway.

→  Grab dinner out . I love Geddy’s, Side Street Café, and the Happy Clam Shack for lobster rolls if you’re up for a short drive outside of town.

→ If you have the time, you could also drive up Cadillac Mountain for sunset. While it’s famous for sunrise, I also love sunset on a clear night and it’s usually less crowded.  Note that this requires advanced planning and reservations late May – October.

Sunset on top of Cadillac Mountain.

Day 5: Explore Acadia National Park

Today’s THE day – Acadia National Park! Known as the “Crown Jewel” of New England, the park spans over 70 acres on Mount Desert Island, and offers some of the most iconic and famous scenery in the region.

Best Things To Do In One Day In Acadia :

→  Start with sunrise at the top of Cadillac Mountain . You can also save this for the following morning.Depending on the time of year, you may have to wake up very early for this, so it’s definitely not for everyone. But if it works with your schedule, I do think it’s worth it. It’s one of the most popular activities in the park for a reason!

Note :  Reservations are required late May – October to drive the auto road to the Cadillac Mountain summit . They release 30% of the available reservations 90 days in advance, and 70% of them two days in advance. I recommend setting yourself a reminder to check the weather two days in advance, and if it’s forecasted to be a clear day, making the reservation if this interests you. That way, it’s worth it! If it’s forecasted to be cloudy and foggy, the views won’t be a great.  Click here for reservation info .

→  Drive Park Loop Road , which is one of the most scenic roads in the park that offers so much for little effort. Along this road, you can make stops at Sand Beach, walk the Ocean Path, visit Thunder Hole, and see the Otter Cliffs. Of all these, I recommend parking at Sand Beach and walking Ocean Path to Otter Cliffs and back. It’s flat and easy, and passes by the best views in the park!

→  Lunch at Jordan Pond House . Famous for their popovers and incredible views overlooking Jordan Pond, this is such a fun thing to do in the park. If the weather is forecasted to be nice, I recommend making reservations for outside if you can. They also have a take out café if you want a quicker experience.

This overlook of Monument Beach is along the Ocean Path trail in Acadia.

→  Take a hike, of course!  Some easier to moderate hikes in the park that I love are Great Head, Bubble Rock, and Gorham. If you’re looking for an adventurous hike that’s more challenging, Beehive is the most popular in the park. Great Head is especially nice because you start the trail at Sand Beach, and it offers spectacular views of the coastline. And then you can just leave you car in the parking lot and walk Ocean Path.

→  Head to Bass Harbor Lighthouse for sunset . It’s about 30 minutes from Bar Harbor, but on a nice night, sunset here is really beautiful. You’ll need to climb out onto the coastal rocks to see the lighthouse, and parking fills up fast. But if you come prepared with sturdy footwear and arrive early enough, it’s wonderful!

→ If you don’t feel like driving to Bass Harbor Light, I would head back to Bar Harbor to  relax and enjoy your last night in town  with a dinner out.

→ You can also try to make a reservation for  sunset on top of Cadillac Mountain  in the park if you weren’t able to go for sunrise!

The views at the top of Cadillac Mountain.

Psst!  Do you have longer to explore the park? Want more information on everything mentioned above? You may want to check out my  Perfect Acadia National Park Itinerary .

Day 6: Drive To Boothbay Harbor

You have the option to start your day with a sunrise on Cadillac Mountain if you weren’t able to plan it the day prior! If you do, I suggest having breakfast at  Jeannie’s Great Maine Breakfast  in Bar Harbor afterward before heading out. They usually open early in-season for everyone getting up to see the sunrise ☀️

The drive to Boothbay Harbor is about 2 hours and 45 minutes without stops, and you also have the option to take the more scenic route and visit some of the suggested stops I detailed in the Day 3 portion of this itinerary. I would go back and reference those if you want to break up the drive.

Why do I recommend the night in Boothbay Harbor?  Well, I just love this little coastal town because of its charm, beautiful scenery, slower pace, and all the amazing boat tour options. From Boothbay Harbor, you can take a boat tour out to a puffin colony, head out on a Schooner, or take a lobster trap haul and lighthouse scenic tour. After exploring Acadia the day prior, it’s nice to stop in a town that forces you to slow down a bit, too.

Boothbay Harbor.

Best Things To Do In Boothbay Harbor:

→  Take a boat tour!  In addition to Camden, this is another one of the best places in Maine for some kind of tour out on the water just because of how many different kinds are offered. Plus, the scenery around this area is absolutely beautiful.

The Lobster Haul, Lighthouses & Seals tour in Boothbay Harbor.

These are the top tours I recommend in Boothbay Harbor:

✓  Schooner Day Sail

✓  Schooner Sunset Sail

✓  Lobster Haul, Lighthouses & Seals Tour

→  Cabbage Island Clambakes!  This is SUCH a cool, unique, and authentic Maine experience for dinner. You’ll take a boat from downtown, and be brought to the family’s private island for a traditional New England style clam bake dinner, which includes their famous blueberry cake and gorgeous waterfront scenery.  Advanced reservations required.

→  Coastal Maine Botanical Gardens . Located just outside of the downtown area, this is such a beautiful place to explore. Don’t forget to snap your photo with the giant wood troll sculptures!

→  Explore the cute and colorful downtown area .

→  Walk the footbridge , which connects both sides of the harbor.

→  Grab ice cream from Downeast Ice Cream , which is one of my favorites in New England.

Downtown Boothbay Harbor.

Where To Eat In Boothbay Harbor :

• Boathouse Bistro
• Boothbay Lobster Wharf
• Shannon’s Unshelled
• Robinson’s Wharf in the neighboring town of Southport is also worth it!

Psst!  I have a post all about  things to do in Boothbay Harbor , if you want some more ideas 😉

Day 7: Drive To Portsmouth & The Essex Coastal Scenic Byway

Portsmouth, New Hampshire.

Making your way back to Boston, there are so many wonderful places you can stop on the way! In fact, it’ll be hard to choose because there’s a lot you can pack in on this portion of the drive, especially along the Essex Coastal Scenic Byway in Massachusetts.

Customize this day how you’d like, but if you’re feeling ambitious and you have enough daylight hours in your day, you can see Portsmouth,  and  all the best towns in the along the Scenic Byway.

Things To Do In Portsmouth In A Few Hours :

Portsmouth is very walkable and compact, so you can see the highlights, even with just an hour or two!

→  Market Square , which is the main shopping area downtown. You’ll find lots of great boutiques and eateries in this section of town.

→  Walk down a cute alleyway to Elephantine Bakery  for a coffee and a sweet treat.

→  Walk over to Prescott Park  for lovely waterfront views and a garden.

→  Visit the   Strawbery Banke Museum  to see history come to life (open seasonally). If you don’t go to the museum, definitely walk around this area because you’ll see lots of historic houses nearby.

Once you’re done in Portsmouth, take a 30 minute drive to Newburyport  and explore there for a bit. This is where I recommend starting the Coastal Byway drive. Follow the Byway through Ipswich, Rockport, Glouster, Manchester By The Sea, and Salem (which is just outside of Boston).

These are the best stops to make along the Essex Coastal Scenic Byway:

→  Newburyport : One of my favorite places to visit in New England, it’s home to amazing shops and such a charming downtown area that sits on the waterfront. Allow about an hour to walk around, grab lattes and whoopie pies from Chococoa Café, and explore the shops.

Psst!  I have an entire guide on  things to do in Newburyport, MA & Plum Island  if you need more info!

Newburyport, Massachusetts.

→  Crane Estate & Crane Beach in Ipswich . This historic estate is so stunningly beautiful, and the beach nearby is the best on the North Shore. Each requires separate admission fees, and you’ll want to budget your time wisely.

Crane Beach in Ipswich.

→  Rockport : One of my all-time favorite coastal towns in New England, Rockport is probably the one place I recommend you don’t miss on the drive. It’s very small, but offers an authentic New England fishing village atmosphere with colorful storefronts, lovely art galleries, great dining, and the most painted building in the country – Motif 1 (which was also featured in the movie  The Proposal ).

Psst!  I have an entire guide on  things to do in Rockport, MA  if you need more ideas!

Rockport, MA.

→  Gloucester is the best place to stop if you have your heart set on a whale watch tour  (but you can also take one that departs from Newburyport if that’s more convenient). Whale watch tours in this region are world-class, and head out to the famous Stellwagen Bank National Marine Sanctuary, which is known for its active marine wildlife.

🐋  Click here to check rates & availability for a whale watch tour from Gloucester

Note : While I do love to visit Gloucester, I think with this amount of time, it’s best to focus your itinerary on the other towns along the drive that I’ve recommended, as I think their scenery is more idyllic than Gloucester. Gloucester is also a city, and is bigger and more spread out, so harder to see on limited time. I do recommend it for a whale watch tour, though! If you take the whale watch tour, just know that it will take at least 3 hours, and likely a bit longer.

→  Manchester-By-The-Sea  is a beautiful coastal town that can easily be seen in about an hour or so. very picturesque scenery, and it’s home to a lovely beach called Singing Sands.

→  Salem . I’m sure you know it as a top Halloween destination, but it’s honestly great year-round. Filled with historic New England charm, waterfront areas, and some fun places to eat, it’s also very walkable!

Psst!  I have an entire guide on taking a  Salem, MA day trip  if you want more information for your visit!

Marblehead, Massachusetts.

→  Marblehead  is such a beautiful town along the North Shore just south of Salem that often gets overlooked, but I absolutely love it here. Also filled with historic charm and lovely waterfront scenery, it’s got a quaint Main Street with some cute shops, a beautiful waterfront park, and some nice places to eat.

Psst!  I have an entire guide on  things to do in Marblehead, MA  if you’re looking for more ideas 😉

More Optional Stops : If you’re looking to explore more of Maine’s coast, there are a few more stops you can make on your way from Boothbay Harbor to Boston. I know, I know – I’m probably tempting you to expand your trip even further, but I’m okay with that 😂

→  Georgetown Island to visit Five Island Lobster Company , which is one of the best lobster rolls in Maine you can get. They’re only open seasonally, and the scenery around there it is very quintessential Maine.

Doubling Point Lighthouse.

Squirrel Point Lighthouse.

→  The Arrowsic Lighthouses . There are two in this area that I really love: Doubling Point and Squirrel Point. Doubling Point requires a drive down a very bumpy dirt road, and Squirrel Point requires about a 3/4 mile hike through the woods, but they’re both beautiful, small lighthouses on the Kennebec River.

Note :  Doubling Point is closed until further notice for repairs. I’m monitoring this and will update once renovations are complete!

→  Bailey Island , which is a very small little island that’s accessible by car, and about a 20-minute detour each way. The best thing to see here is the Giant’s Stairs Trail, which offers beautiful coastal views, and giant rocks you can climb around (just practice caution, of course!). There’s also a cute little place to eat right by the bridge called Sundrenched, which is waterfront and has outdoor seating. This is a nice place to get off-the-beaten-path.

Giant’s Stairs on Bailey Island.

Day 8: Head Back To Boston

It’s the end of your trip! Depending on when you need to make your way back home, or to the airport, you may have some time in the morning to explore a few of the places I mentioned above, but I left this day open in case you have to catch an early flight, or start your drive back home early.

If you do happen to have some time on this day to explore, I would suggest you end the previous day in Rockport, and then explore Salem and Marblehead on this day before heading back to the airport.

Optional Itinerary Adjustments

→ If you have more time and are a city person, I would recommend adding a night to Portland and Boston.

→ If you have extra time and don’t want to add a night to a city, I have two suggestions.  First option : add a night to Camden to spend a day exploring the nearby attractions (lighthouses, Rockland, etc.) to make the drive from Portland to Camden easier.  Second option : add a night to Bar Harbor to see more of the park, and enjoy more hiking.

→ If you have even longer, you could make this a 2-week adventure by driving up the coast of Maine to Lubec, and then crossing the Canada border to the charming town of St. Andrews by the Sea, and Campobello Island. You could also take the CAT ferry from Bar Harbor to Nova Scotia.

I have a detailed guide on  visiting Lubec, Maine , if you wanted to explore places further north!

Best Towns To Stay In On The Drive

For an overnight stay, these are my suggestions on the best places to stay based on experience when it comes to options for dining and accommodations (plus, lovely scenery, of course!). You’ll just want to pick where you stay based on how far you want to drive each day.

As you saw in my itinerary, I included some suggestions for overnight stops, but you may want to customize this trip to your liking (which I encourage!), so I wanted to provide you with more options. It’s also good to know that you won’t have time to stay overnight in all these places unless you extend your trip, but you  will  be able to, at the very least, drive through them all.

→  Rockport, MA : Not far from Boston, and if you’re looking get a leisurely start or slow-burn end to your trip, I really love to recommend a stay in Rockport. Most everything is pretty walkable, with cool shopping, nice hotel options, and idyllic scenery.

Where To Stay In Rockport :

✓  The Cove at Rockport

✓  Addison Choate Boutique Hotel

→  Portsmouth, NH : As mentioned, fantastic dining and shopping, with lots to keep you busy in the evening after you arrive! Plus, the historic charm is really quite lovely.

Where To Stay In Portsmouth :

✓  The Hotel Portsmouth

✓  Hotel Thaxter

→  Kennebunkport OR Ogunquit : Both of these charming coastal towns that are very close to on another, and both make for a great overnight stay. Kennebunkport has more options for nicer accommodations, but Ogunquit has a gorgeous beach. Both have very charming downtowns that are easily walkable with lots of places to eat and shop! Just pick based on what vibe you’re going for: beachy or just traditional coastal.

Where To Stay In Kennebunkport :

✓  Captains Collection Historic Inns

✓  The Boathouse

Where To Stay In Ogunquit :

✓  Anchorage By The Sea

✓  Cliff House : Technically in York, but a short 10-minute drive to Ogunquit. I like to suggest it because it’s a fantastic resort with amazing coastal views, and worth the splurge! It also makes my list of the top  New England resorts and spas  😉

→  Boothbay Harbor : I love stopping here for a night or two every time I make this drive. It’s very small and easily seen in a few hours, and I like to stay the night so I have the option to take a boat tour. I also find the shops and restaurants really great.

Where To Stay In Boothbay Harbor :

✓  Harborage Inn On The Waterfront

✓  Spruce Point Inn

→  Camden : Lastly, I think Camden is the best place to stay before reaching Bar Harbor. Built around a gorgeous harbor, the coastal scenery here is beautiful, and it’s a known sailing destination. There’s also a great Main Street for shopping and dining.

Where To Stay In Camden :

✓  Camden Harbour Inn

✓  Lord Camden Inn

Where To See Fall Foliage Between Boston & Bar Harbor

Manchester By The Sea in the fall season.

If you happen to be planning your trip to coincide with fall foliage, then I would love for you to consider adjusting the itinerary slightly (but don’t worry, it’s not too different!). Most places already on the itinerary offer amazing foliage color. Here are some suggestions to keep in mind:

→  The Essex Coastal Byway in Massachusetts is GORGEOUS in the fall  with lots of foliage color. I’ve done this drive during peak foliage, and I was shocked at how beautiful it was. Manchester-By-The-Sea, Essex, Salem, and Newburyport are especially beautiful in the fall. And, of course, Salem is  famous  for its October festivities!

→  Portsmouth offers some really lovely fall foliage  during this time of the year. It’s also an especially cozy place to visit because of all the historic New England architecture.

→  Boothbay Harbor  is also amazing in the fall, and the entire harbor is surrounded in fall color. Head out on a boat tour to see even more beautiful fall foliage! Tours usually end around mid-October, so there are typically opportunities that coincide with peak foliage.

→  Camden is also spectacular in the fall . I definitely recommend hiking or driving up the Mt. Battie Auto Road to take in the views of the harbor from above. It’s the best during foliage season!

→  Kennebunkport  also offers some beautiful fall foliage. Having been in October a few times, the fall season always impresses me in this coastal town.

Kennebunkport, Maine in October.

→ Of course,  the starting and end points on this road trip are stand-outs in the fall, too.   Acadia National Park  is stunning in the fall season with foliage color, and  Boston  is also amazing this time of the year. Although, it’s good to know that Boston tends to peak later in October, so in the fall, you may want to plan to spend more time in Boston at the end of your trip to get a glimpse of some foliage color.

What To Pack For This Road Trip

This will depend entirely on what time of year you visit, so plan accordingly based on the season when it comes to clothing and footwear. Beyond that, here are some things I recommend you bring regardless of what time of year you visit.

→  Light sweater or jacket  – even in the summer! If you plan to take any boat tours or get up for sunrise at Cadillac Mountain, you’ll want this to stay warm.

→  Reusable water bottle  to stay hydrated.

→  Dramamine  if you plan to hop on a boat tour and tend to get seasick.

→  Comfortable shoes  – I know this seems obvious, but you can leave your fancy shoes at home. I usually wear a really comfortable pair of sandals in the summer, or sneakers in the spring/fall. If you take a boat tour, they may have some requirements on the type of footwear you wear, so double check that, too.

→  Hiking boots  if you plan to tackle any trails in Acadia. You’ll be happy to have the ankle support.

→  Camera, of course!  You’re going to see so much incredible scenery on this trip, you’ll want to capture the best memories along the way. This is a good trip to get a tripod if you don’t have one – they even make inexpensive ones for iPhones that are perfect for just about anyone.

Tips For This Road Trip

→  Offline maps  on your GPS! You’ll have cell phone service in most places, but when you’re near a beach or inside Acadia National Park, you may lose service.

→  Be ready to pay tolls on the roads . If you’re renting a car for the trip, I suggest making sure your rental comes with an EZ Pass for the toll roads to make things easier. Most of them in this area are now cashless and don’t require you to stop – you just get a bill for the tolls instead, which you can work out with your rental company.

→  Bring Some Cash  – I know this seems obvious, but as someone who  never  carries around cash, I’m always reminded when I make this road trip that some places still don’t take credit cards! Usually places like ice cream stands and seafood shacks are the ones that may be cash only, so it’s good to have a small amount on you at all times. Better yet, get a debit card that reimburses you for ATM fees, like the Charles Schwab checking card. Most places will take cards, though.

→  Prepare for crowds at popular places . Depending on the time of year you take this trip, most places will bring in some level of crowds. The most popular destination is Bar Harbor and Acadia National Park, and this is where you can expect the biggest crowds. If you travel in spring or fall, you’ll see fewer people, but places will still be lively.

→  Prepare for the cost . New England in general is just an expensive region to visit, unfortunately, and prices tend to be higher than other parts of the country.

More posts you may enjoy:

• The BEST 7 Day New England Road Trip Itinerary
• The PERFECT Fall Foliage New England Road Trip Itinerary
• The Best Time To Visit New England
• Incredible Lighthouses In New England To See
• Maine Lighthouse Road Trip Itinerary
• Gorgeous New England Islands Worth Visiting

That’s A Wrap On The Boston To Bar Harbor, Maine Road Trip!

And there you have it! After years of perfecting it, I’m thrilled to finally share my unforgettable Boston to Bar Harbor, Maine road trip itinerary with you. I truly believe that the New England coast is such a special and memorable region to experience for yourself, and with this guide, you’ll see the very best it has to offer. Happy planning!

The Vanderbilts Would Have Been Scandalized by This Sleek Waterfront House

Gilded Age, meet the modern age!

In an era of homogeneous highways and interchangeable subdivisions, there remain a few American locales whose mere names conjure an entire world and aesthetic. Places like Nantucket, New Orleans, and Charleston have clung to a unique identity, enshrining vernacular style in residences and downtowns in hopes of warding off the encroachment of sameness.

A surprisingly large number of the houses still stand, clustered around the deep-water harbor that attracts yachts and regattas. Some have remained as family homes or become trophies for newcomers like Oracle founder Larry Ellison. No matter whose name is on the deed, though, one thing you do not associate with Newport is modern architecture.

Which is why in the spring of 2020, when the ELLE DECOR A-List architect and designer Poonam Khanna, founder of the New York City–based firm Unionworks , received a call from Charlotte Wagner, a Boston art collector and philanthropist, she was intrigued.

Wagner and her husband had bought a waterfront plot with a teardown Victorian where they were building a weekend retreat. As longtime collectors of edgy blue-chip works—Wagner is a trustee of Boston’s Institute of Contemporary Art—they wanted a definitively modernist house, but it had to be sited, designed, and crafted with the similar level of care as the original grand homes. “We wanted to honor the excellence that distinguishes this community,” Charlotte says.

Most of all, the house had to establish a strong connection to the landscape, inside and out. It was an ideal match for Khanna, who in her decades of practice has developed a reputation for balancing minimalism with a quiet, organic grace. She is a master of materials, using metals, wood, and boldly figured stone in a way that seems entirely fresh.

Tour This Modernist Home in Newport

Designed by the Boston-based architect David Stern , the property—a main house and a guest cottage connected by a rain garden—seems almost to blend into the reedy, windswept surroundings. With its flat roof and mahogany rain screen, the silhouette is low slung and severe, in the modernist tradition, but because a big portion of the lower level is a breezeway leading straight to the sea, it feels as airy as a length of driftwood. Over time, the untreated mahogany will gradually turn silver, adding to the effect.

The couple’s principal residence in Cambridge, Massachusetts, is filled with statement furnishings, including works by the Milanese architect Vincenzo De Cotiis, a perfect foil to art by Cecily Brown, Glenn Ligon, and Alice Neel. In Newport, by contrast, Khanna has created an oasis of comfort and informality. To weave in a sense of beachy serenity without monotony, the rooms, while neutral in palette, are vivid with texture. Khanna edited away noise by repeating materials in unexpected places and playing with different colorways in the same textile on the furniture and surfaces. “We wanted there to be a subtle thread that runs through,” she says, “like ripples of water.”

One of the most compelling inspirations came early in the project when Khanna and Wagner took a walk together around the five-acre property and adjacent beachfront. They scrambled over the formations of local rock, known as pudding-stone, a Paleozoic-era aggregate of rounded pebbles of various shades fused with a neutral sandy background. “We found our palette right there,” Khanna says.

.css-12zwr2e{font-family:Sabon,Sabon-styleitalic-roboto,Sabon-styleitalic-local,Georgia,Times,Serif;font-size:1.625rem;font-style:italic;letter-spacing:-0.0225rem;line-height:1.2;margin:0rem;}@media(max-width: 48rem){.css-12zwr2e{font-size:1.9375rem;line-height:1.3;}}@media(min-width: 48rem){.css-12zwr2e{font-size:1.9375rem;line-height:1.3;}}@media(min-width: 64rem){.css-12zwr2e{font-size:2.75rem;line-height:1.1;}}.css-12zwr2e b,.css-12zwr2e strong{font-family:inherit;font-weight:bold;}.css-12zwr2e em,.css-12zwr2e i{font-style:italic;font-family:inherit;}.css-12zwr2e i,.css-12zwr2e em{font-style:italic;font-family:Sabon,Sabon-styleitalic-roboto,Sabon-styleitalic-local,Georgia,Times,Serif;} “We wanted there to be a subtle thread that runs through, like ripples of water.” —Poonam Khanna

The exterior’s slender verticals carry into the interior, where Khanna plays toward and against that geometry. In the entry, oak wall panels create a warm backdrop for minimal metal stair railings. One of the house’s most spectacular artworks—a wobbly grid of brightly colored squares by the 78-year-old abstractionist Stanley Whitney—stakes out pride of place on the landing.

In the main home’s great room, an asymmetrical U-shaped sofa sets the tone for the layout and flow. The colors of the furnishings echo the landscape; the mix includes a blocky round oak table by Yabu Pushelberg, Danish dining chairs with delicate wooden frames, and a David Weeks chandelier that is as much sculpture as illumination. “The idea was to have a lot of pattern and detail but modulate it at a low volume,” Khanna explains.

In the nearby powder room, she employs her characteristic panache with figured stone. Here, a vanity and wall in richly veined Turkish marble is paired with a vintage French rope mirror. It is this kind of subdued daring—knowing when and how exactly to introduce a graphic slash into that sense of calm—that is at the heart of Khanna’s gentle talent. “The idea is to lull you into relaxation,” she notes. “And then, when you’re ready, bring you back to earth.”

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