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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
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• The Top Statue of Liberty Cruises
• The Top NYC Dinner Cruises

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Boston Harbor Sunset Cruises

Home » Tours & Cruises » Boston Harbor Sunset Cruises

Sunset Cruise in the Boston Harbor

Enjoy the fresh air and escape the heat, see amazing views of Boston’s beautiful skyline and the historic USS Constitution as the sun sets behind the city. As evening sets in, sunset colors fade to a twilight sky and the city comes alive with lights. Our 90-minute sunset cruise will highlight popular and famous scenes of Boston Harbor from both past and present. Snacks, and cold beverages including water, juice and soda; as well as a full bar, are available on every boat.

Dates and Pricing

Weekends only until mid-June

Start times vary as the sun sets earlier each week. Click “Buy Tickets” to see start times for the specific day.

(Ages 18-59)

Students (13-17 with valid ID) / Seniors (60 and up) / Military (with valid ID)

(Ages 6-12)

(Ages 5 and Under)

• *Plus 10% service charge.

Contact Information

• 60 Rowes Wharf Boston MA 02110

Book Direct Online

Tickets may also be bought at the Wharf, Ferry Terminal Center.

Non-refundable, can be rescheduled with 24 hours notice. Once purchased, tickets cannot be refunded. You may reschedule your tickets (subject to availability) only if you do so at least 24 hours in advance. Activity takes place rain or shine. The activity runs regardless of weather conditions. In the rare situation where the seller is forced to cancel the event, ticket-holders will be allowed to reschedule to another time (subject to availability).

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Architecture Tours

Opening day for our 2024 season is may 24th.

Embark on a guided tour with spectacular views of Boston's historical and contemporary architecture.

• Full Bar Available
• Handicap Accessible
• $4.00 Parking

2024 Architecture Tours Schedule

May 24 – Sept 1 Fri-Sun 10:00 am 

Sep 7 – Oct 20 Sat-Sun 10:00 am

Ticket Rates

• Adult $43.00
• Senior / Student $38.00
• Child Under 12 Years $33.00
• Child Under 3 Years $6.00

*Excludes 5% MA Convention & Facilities Surcharge  

Discover Boston's Iconic Buildings

This 2-hour tour, hosted by Charles River Boat Company, offers spectacular views of historic and contemporary architecture along Boston Harbor, the Charles River Locks, and the Charles River basin. The tour— narrated by a guide from Boston By Foot and co-sponsored by Boston Society for Architecture, a center for architecture and design—includes landmarks such as Marriott’s Custom House, the Prudential Building, and the Hancock Tower, as well as cutting-edge contemporary design by today’s top architects. These are simply the best waterfront views of Boston and Cambridge.

Architecture tours depart from Lechmere Canal, The ticket booth and boat departure is located outside the doors at the canal side of the CambridgeSide Mall.

Click here to view our tour featured on “Chronicle”

Cambridgeside

CambridgeSide Mall 100 CambridgeSide Place Cambridge, MA 02141

Our boats board at the Lechmere Canal, which is directly outside the doors at the canal side of the CambridgeSide Mall. Park in the CambridgeSide Mall Parking Garage then proceed to the first floor and the ticket booth and boat can be found outside on the canal side of the mall.

From North of Boston

Take Interstate 93 exit 26 for Storrow Drive / North Station Keep right at the fork, follow signs for 28 North / Leverett Circle / North Station Slight right at Nashua St Turn left onto Nashua St Take the 1st right onto MA-28 North / Monsignor O’Brien Highway At the next light turn left onto Edwin H Land Boulevard At the next light turn right onto CambridgeSide Place Park in the CambridgeSide Mall Parking Garage. Our boats board at the Lechmere Canal, which is directly outside the doors at the canal side of the CambridgeSide Mall

From South of Boston

Take Interstate 93 exit 26 toward Storrow Drive / North Station Keep left at the fork, follow signs for MA-28 North / Leverett Circle / North Station Slight right at Nashua St Turn left onto Nashua St Take the 1st right onto MA-28 North / Monsignor O’Brien Highway At the next light turn left onto Edwin H Land Boulevard At the next light turn right onto CambridgeSide Place Park in the CambridgeSide Mall Parking Garage. Our boats board at the Lechmere Canal, which is directly outside the doors at the canal side of the CambridgeSide Mall

From West of Boston:

Take Route 90 – Mass Pike Exit Left at Cambridge/Allston Tolls – follow signs to Cambridge Proceed through lights and over River Street Bridge (Charles River) Immediately turn right at other end of bridge and travel East on Memorial Drive Stay on Memorial Drive – The CambridgeSide mall is approximately 3 miles on the left across from the Sonesta Hotel

Park in the CambridgeSide Mall Parking Garage. Our boats board at the Lechmere Canal, which is directly outside the doors at the canal side of the CambridgeSide Mall

From The MBTA (Public Transit)

Take the Green Line “E” train to Lechmere Station Exit the train, cross Mcgrath highway and Cambridge St. After crossing Cambridge St., walk down First Street St. Take a left at Canal Park and this will take you into the Lechmere Canal  Follow the footpath to the right, the docks are located outside the canal side doors at the CambridgeSide Mall.

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EXPLORE AN ISLAND PARK JUST MINUTES FROM DOWNTOWN BOSTON

The official website of the boston harbor islands.

Made up of 34 islands and peninsulas, Boston Harbor Islands National and State Park is an urban oasis just minutes from Boston’s city center. Hop aboard a park ferry and discover islands rich with opportunities for outdoor recreation, relaxation and learning. Check the park calendar for special events or create your own adventure with our trip planning tools below.

Getting here is half the fun! Explore ferry schedules, view ticket prices, and reserve tickets in advance.

Ferry Schedules

Discover ways to join our community and to give back to your park!

Get Involved

Stay up to date with video content created by park staff about the harbor and islands.

Mini-Grant Program

Innovation islands.

The Innovation Islands program awards mini-grants of up to $5,000 to local community leaders to design, promote, and facilitate programming on and around the Boston Harbor Islands. Learn more about this year's mini-grant recipients and find out how to apply for a mini-grant for your community.

Upcoming Events

Stewardship Saturday at Grape Island

Stewardship Saturday at Spectacle Island

Join Boston Harbor Islands National & State Park in commemorating Juneteenth, and to learn more about Black history in Boston.

Vintage Base Ball

Step back in time and watch a 19th Century base ball game with original rules and uniforms!

Sunset Lighthouse 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.

Jazz on the Porch

Relax to the sounds of jazz standards and original music performed by Berklee College of Music on Spectacle Island.

Find Your Better Nature

Boston Harbor Islands

Mooring information.

Mooring reservations at Spectacle, Georges, and Peddocks Islands are now on Dockwa. Learn more about bringing your boat to the Boston Harbor Islands.

Explore the Islands

Exploring is believing! Of 34 islands and peninsulas that make up Boston Harbor Islands National and State Park, many are accessible by seasonal public ferry service or can be accessed year-round by car or on foot. Islands range from rustic retreats to family-friendly hubs with a range of activities. Hover over the map to learn more about each island destination!

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Photo gallery.

It's great to be able to get away from the city for a day and experience the outdoors in the harbor just a few minutes by boat from Boston. Will from Dorchester

I feel like I'm walking through history right now! Harbor Discovery Camper

Gorgeous views, quiet vibe, clear waters. Great spot to spend a summer day or weekend. Danielle from Quincy

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Classic Style Charter Boat and Tour Boat Fleet

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Boston Harbor

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70 Rowes Wharf

Boston, MA 02110

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What a beautiful harbor!!! The harbor offers great views and scenery. Additionally, you can dine on a boat on the harbor and enjoy the view. There is a hotel on the harbor called The Harbor Hotel and you can even take a boat ride on one the boats or yachts. It really is just a great spot to hangout, dine, and enjoy the atmosphere.

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Boston Sunset Cruise

Call to order 617-951-2460

Cruise on a sailboat or luxury yacht through Boston Harbor to end your day or start your evening.  Set sail aboard one of our classic boats for an experience you are sure to never forget!  Sail through Boston Harbor and glide past the U.S.S. Constitution as the sun dips beyond the outline of Boston’s skyline. Take in the rich colors of the sky with a glass of Champagne in hand and the breeze in your hair. Allow us to help you sit back and relax and enjoy the most perfect Boston sunset cruise.

Whether you are on our sailing boat, or our motor yacht, our exceptional crew is sure to treat you with the most professional hospitality that will have you feeling that it is your own yacht. Cruise Boston aboard one of our classic boats for a peaceful and picturesque sunset. Whether you are sightseeing or wanting to take in the views, it is the perfect way to end your day.

-->Boston Sunset Cruise -->

Join us for a Boston Sunset Cruise as an after work cruise to relax with friends and watch the sky as it changes from blues to oranges behind the outline of Boston’s city skyline. Experience a sunset cruise departing from bustling Rowes Wharf and head out to watch the sun go down over the city of Boston. Bring a date or meet a group of friends aboard the classically styled yacht, Northern Lights . Cruise by the U.S.S. Constitution at dry dock in the Charlestown Navy Yard and wait for cannon fire to announce the setting of the sun.

-->Evening Jazz Cruise -->

Grab that special guy or gal, or a couple of happy-footed friends who enjoy the sounds of music on our 90-minute live jazz cruise in Boston Harbor. Allow your senses to take you back in time with the sights of our 1920s styled New England Yacht combined with sounds of jazz. Our jazz cruise is preformed by Blue Motion Quartet, which brings a blend of vibrant modern groove with a standard jazz repertoire. Cruise through the harbor enjoying the City Lights as they dazzle on the waters of Boston Harbor, grab a glass of champagne or a mixed drink from the bar and dance with your sweetheart on this one of a kind cruise.  This is the perfect cruise for snuggling up with a loved one’s or dancing with a group of friends to the sounds of the Blue Motion Quartet. 

-->Boston Sunset Sail -->

Experience a beautiful Boston Harbor sunset on the water and see some of the city’s waterfront landmarks as the sun dips below the horizon. Sailing offers a smooth and gentle experience on the water, which is great for having a romantic early evening out with that special someone. Our crew and captain offer top notch customer service to our guests.

-->Cocoa & Carols Holiday Cruise -->

Come aboard our luxury yacht Manhattan decked out in Holiday decor for an evening of holiday cheer. Enjoy a cruise out into Boston Harbor that is perfect for everyone in your family. Holiday favorites will fill the air to set the perfect mood for Holiday spirit.  This is Boston Holiday Cruise that is not to be missed. Cozy up with some hot cocoa, and treats for the whole family. Sit back, enjoy the view, the music, and the holiday cheer with this Boston Holiday Cruise.

-->Holiday Sunset Cruise -->

Step aboard the luxury yacht Manhattan decked out in Holiday decor for a Boston Harbor Holiday Sunset Cruise.  Our captain will provide light commentary of Boston Harbors sightseeing highlights. And enjoy light Holiday music as it will be played throughout the trip. Watch the sky as it changes from blues to oranges behind the outline of Boston’s city skyline.

-->Romantic Valentine’s Jazz & Champagne Cruise -->

Romantic Valentine’s Day Jazz & Champagne Tasting Cruise. Start or end your romantic evening with a light champagne tasting and stunning views of Boston. While sipping on your champagne, enjoy romantic jazz tunes by our house jazz band as we glide through the harbor. While fireworks are not included in this cruise, we hope to create metaphorical sparks for you and your date.

-->Sunset Sail aboard Schooner Adirondack II -->

Join us for a Boston Harbor Sunset Sail aboard Schooner Adirondack II! Experience a Boston sunset from the water on this evening sight sail. Enjoy one of our classic sailing yacht for an evening of fun and relaxation. Get away from the hustle and bustle of everyday life. Your knowledgeable captain and crew are always ready to answer questions about the sights and history of Boston Harbor. Sail and take in the surrounding areas, and feel free to ask them whatever you like! While you experience the joy of a leisurely sailing cruise, you’ll see all of the amazing views Boston Harbor has to offer! 

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Sail out from Rowes Wharf and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

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Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

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27 Birthday Restaurants in Boston To Celebrate Your Special Day in 2024

Feeling stuck in a birthday rut? Perhaps it's time to discover fresh birthday restaurants in Boston to celebrate your special day. If you're feeling unsure about making a choice, don't worry. We've compiled a list of the best spots to host a birthday dinner in Boston.

Boston stands as one of the oldest and most historic cities in the U.S. From being home to the oldest subway, the first chocolate factory and a public park in the country, Boston's historical significance is undeniable. While renowned for events like the Boston Tea Party and teams like the Boston Celtics, the city's vibrant history has also shaped its diverse culinary landscape. Below, we’ve curated a list of numerous birthday restaurants in Boston that you should contemplate visiting for your special day. We hope that these inspire some fantastic birthday ideas in Boston.

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27 Best Birthday Restaurants in Boston

Learn to cook boston foods.

If you want to eat hearty Italian food, come to Giulia . T his birthday restaurant near Boston combines Italian pride and love for food, providing a blend of passionate cooking with homey hospitality.  

The perfect recipe for a birthday restaurant in Boston, this is a laid-back Italian restaurant that brings passion to its dishes whilst providing a relaxing atmosphere.

What to Order

The pappardelle and bucatini all’amatriciana are very popular dishes, showcasing the best Italian flavors of this popular birthday restaurant near Boston. 

Giulia | 1682 Massachusetts Ave., Cambridge, MA 02138  | $$

A cornerstone of the Cambridge dining scene,  Harvest celebrates local farmers and Boston foods with its fresh, seasonal menu. For over 50 years, this birthday restaurant near Boston has offered delightful al fresco dining, perfect for any special occasion. 

Casual and sophisticated dining. The restaurant provides different experiences through its fireside dining, large bar and spacious patio.

The apple walnut salad is a favorite among healthy diners. The heritage breed pork chop is also a must-try. 

The Harvest | 44 Brattle St., Cambridge, MA 02138 | $$$

3. Little Whale

If you seek a birthday restaurant in Boston where you can enjoy delicious seafood, Little Whale is the spot for you. Chef Michael Serpa has created a staple menu that celebrates the seafood of New England’s coast, perfect for your celebration.

The Little Whale offers both casual and sophisticated dining. Enjoy raw bar favorites and fish sandwiches for a relaxed meal, or opt for larger mains to have a more upscale experience.   

The Maine lobster roll served with fries is highly recommended.

Little Whale | 314 Newbury St., Boston, MA 02115 | $$

4. La Brasa

If you're in the Sommerville area looking for a Boston birthday restaurant with wood-fired and casual dining,   La Brasa is the spot for you . The menu changes often as they serve local New England produce. Its creative street food, salads and meat roasts are cooked to a very high standard.

This birthday restaurant near Boston offers a family-friendly casual dining experience that centers open flame cooking.

The shrimp pupusa is a great appetizer. For your main course, try the roasted chicken and savor every bite.

La Brasa | 124 Broadway, Somerville, MA 02145 | $$

5. Lincoln Tavern and Restaurant

If you are looking for a birthday restaurant in Boston that mixes hearty food with a laid-back experience, where you can chat and drink cocktails with friends, you should visit the Lincoln Tavern and Restaurant .

A flexible bar and birthday restaurant in Boston that prioritizes giving all visitors the space to have a good time.

The French onion soup is a delight. Also, don't miss out on the al pastor pizza or the Lincoln burger.

Lincoln Tavern and Restaurant | 425 W. Broadway, Boston, MA 02127 | $$

Located in a beautiful and bustling neighborhood, Duexave boasts stunning surroundings with lush trees, picturesque promenades and historic architecture. The food matches the elegance of the location, as this birthday restaurant in Boston takes pride in the modern French food it serves.

The establishment has an elegant and chic interior, where guests can enjoy high-end food amongst the historic Back Bay.

Try the crispy duck confit to begin, then indulge in some pan-seared scallops. You will not be disappointed.

Deuxave | 371 Commonwealth Ave., Boston, MA 02115 | $$$

Forget about all your problems and enjoy quality time with loved ones at Sarma , a modern Mediterranean birthday restaurant near Boston that focuses on providing meze and delectable Middle Eastern dishes. 

Modern architecture that perfectly complements the small-plate style menu.

From the many dishes available to share, make sure to try the fava bean paté, the seven-layer hummus, the harissa barbeque duck or the Brussels sprout bravas.

Sarma | 249 Pearl St., Somerville, MA 02145  | $$

8. Shōjō 

Nestled in historic Chinatown, Shōjō is the perfect birthday restaurant in Boston for a large and casual celebration, offering exquisite modern Chinese cuisine alongside an impressive Japanese spirit list.

A laid-back gastropub that seamlessly blends modernity with tradition.

The wagyu beef dumplings and the kimchi fried rice are highly popular among locals.

Shōjō | 9A Tyler St., Boston, MA 02111 | $$

9. Wusong Road

For a unique twist on Chinese cuisine, visit Wusong Road , a fusion restaurant in Cambridge . With its vibrant tiki bar atmosphere, it's a must-visit for anyone seeking birthday ideas in Boston. 

A birthday restaurant near Boston with a funky and modern vibe that welcomes all with care and gratitude.

The pork bao buns and crab rangoon are popular choices, but be sure to explore the menu for other hidden gems. 

Wusong Road | 112 Mt Auburn St., Cambridge, MA 02138  | $$

10. Frenchie Wine Bistro

If you seek a modern birthday restaurant in Boston, visit Frenchie Wine Bistro , an easy-going wine bar  that cares deeply for its customers and serves delicious French-inspired food.

Relaxed and casual, this spot also has a romantic garden-side solarium, perfect if you're looking for date ideas in Boston .

The mushroom buckwheat crêpe is a fantastic savory dish.

Frenchie Wine Bistro | 560 Tremont St., Boston, MA 02118 | $$

11. Neptune Oyster

Are you a seafood lover? Neptune Oyster isn't just a place to eat; it's a culinary destination renowned for its fresh seafood and oyster bar offerings. 

Whether you're enjoying a solitary moment at the bar or celebrating with a large group, the friendly staff at this seafood birthday restaurant in Boston will delight you.

The Neptune burger and the Maine lobster roll are gorgeous classics. If you fancy something from the oyster bar, the sea urchins and shellfish are wonderful. 

Neptune Oyster | 63 Salem St., Boston, MA 02113 | $$$

12. 1928 Beacon Hill Boston

Want to find a birthday restaurant in Boston that serves elegant bourbon and cocktails alongside traditional food? Then put the 1928 Beacon Hill on your list. 

Elegant 1920s style makes this birthday restaurant in Boston memorable, with an ambiance that steals the show.

If you’re visiting during the day, try the fish and chips with New England haddock. For dinner, indulge in the lobster tortellini.

1928 Beacon Hill Boston | 97 Mount Vernon St., Boston, MA 02108  | $$$

13. The Barking Crab

Along the historic Fort Point Channel, The Barking Crab   is a notable birthday restaurant in Boston with a welcoming atmosphere . Created in 1994, this eatery serves seasonal food, including its famous lobster rolls.

Transitioning from seasonal outdoor eating to a year-round operation, this establishment now offers a perfect setting for cozy winter nights and hot summer days alike.

The fisherman's platter and any of the lobster rolls are absolute favorites.

The Barking Crab | 88 Sleeper St., Boston, MA 02210 | $$

14. The Maharaja

Arguably the most popular Indian restaurant in New England,  The Maharaja is part of the bustling and lively Harvard Square in Cambridge. If you're seeking a casual and welcoming birthday restaurant near Boston, look no further. 

Renowned for its exceptionally friendly and helpful staff, this establishment offers a delightful dining experience.

The saag paneer is a great vegetarian option alongside the classic tandoori chicken.

The Maharaja | 57 JFK St., Cambridge, MA 02138 | $

Another excellent choice for a birthday restaurant in Boston is Ilona , a bright and modern Mediterranean small-plate spot, perfect for both large and small gatherings.

A lively restaurant that promotes sharing and caring whilst serving sophisticated cocktails.

The octopus is gorgeous. For vegetarians, the crispy eggplant comes highly recommended.

Ilona | 783 Tremont St., Boston, MA 02118 | $$

Although it might not have a Michelin star, O Ya 's quality and setup are that of a Michelin winner. This birthday restaurant in Boston serves omakase-style food, with a set menu offering 20 high-end, delectable dishes.

An upscale and innovative sushi restaurant with wood-paneled décor that is renowned across the world. 

While the menu is set, get ready to savor the hamachi and foie gras. 

O Ya | 9 E. St., Boston, MA 02111 | $$$

17. Bar Vlaha

If you are searching for a birthday restaurant near Boston offering good Greek food for large groups, look no further than Bar Vlaha . This establishment serves shareable small plates and is well known for its taverna-style bar and relaxed atmosphere.

A laid-back, relaxed birthday restaurant near Boston that takes its interior inspiration from traditional Greek village houses.

The succulent lamb chops, the healthy and delicious fried oyster mushrooms and the manitaria are all must-tries.

Bar Vlaha | 1653 Beacon St., Brookline, MA 02445 | $$

A highly acclaimed Japanese-Spanish tapas restaurant in Cambridge,  Pagu   offers a unique dining experience for those seeking a memorable birthday restaurant near Boston. Chef Tracy Chang, inspired by her grandmother's legacy, has crafted an adored restaurant known for its innovative dishes and culinary excellence.

Pagu embodies an elegant and minimalist aesthetic, providing a socially conscious restaurant that provides delightful food whilst supporting the local community.

Black ink bao and the midnight ramen are both very much worth ordering.

Pagu | 310 Massachusetts Ave., Cambridge, MA 02139 | $$$

Expect excellence in every category at Grana , an Italian restaurant situated within the five-star Langham Hotel. Feast on delightful Italian food amongst lush furniture and high ceilings in this high-end Boston birthday restaurant.  

Grana is situated in the former Federal Reserve Bank’s grand hall, where history meets glamour. The restaurant is decorated with famous artwork in a spacious environment.

If you are sharing plates, the burrata, crabs avocado toast and lobster cannoli come highly recommended.

Grana  | 250 Franklin St., Boston, MA 02110 | $$

Crafted by renowned chefs Ken Oringer and David Bazirgan,  Uni   is a birthday restaurant in Boston that specializes in Asian street food . Here, guests can enjoy a mesmerizing dining experience and even opt for room service if staying at The Eliot Hotel.

A chic restaurant within a renowned hotel, this establishment is decorated with gorgeous wood panels and modern architectural influences.

On a high-quality menu, the wagyu beef dumplings continue to be a crowd favorite. 

Uni | 370A Commonwealth Ave., Boston, MA 02215 | $$$

21. Silver Dove Afternoon Tea

Located in Downtown, the Silver Dove Afternoon Tea is a must-visit for those seeking exquisite afternoon tea for their birthday in Boston. If you are looking for fun restaurants in Boston , this is the perfect spot; co-owners Patrick Brewster and Lee Morgan excel at hosting large groups, ensuring a fantastic party experience complemented by the establishment's inviting emerald banquettes.

The Silver Dove is elegant and inviting and, although the menu is set, its service is characterized by its friendly and helpful demeanor.

While everything on the menu is delightful, don't miss the carrot cake and the coronation chicken.

Silver Dove Afternoon Tea | 24 Tremont St., Boston, MA 02108 | $$

22. Abe & Louie's

Indulge in iconic dishes complemented by an award-winning wine list at Abe & Louie’s —  a high-end steakhouse and the perfect birthday restaurant in Boston for a sophisticated and succulent meal. 

With a history dating back to the 1960s and a commitment to excellence, it offers more than just delicious food. The décor exudes timeless elegance, with classic touches that create an upscale ambiance.

The prime-aged Midwestern steaks and the seafood tower served with lobster, shrimp, crab claw and oysters are real crowd-pleasers.

Abe & Louie's | 793 Boylston St., Boston, MA 02116 | $$$

23. Yvonne’s

At the heart of Downtown lies Yvonne’s , a seriously in-demand establishment for large birthday gatherings. From sophisticated cocktails to a global selection of small plates, Yvonne’s is dedicated to creating unforgettable moments for all who cross the threshold.

Marble and mahogany accents make this birthday restaurant in Boston glamorous. You’ll find a welcoming staff, helpful even during the busiest services.

The Thai octopus and the chicken and quinoa meatballs are both delicious options on the menu.

Yvonne’s | 2 Winter Pl., Boston, MA 02108  | $$$

A modern Cuban-inspired birthday restaurant in Boston, Mariel offers the vibrant party atmosphere your celebration deserves. The cuisine pays homage to Cuba’s rich culinary history and cultural influences.

An upscale spot that serves you delicious Cuban-inspired food, it offers a modern rendition of an elegant restaurant — a classic cocktail bar and a vibrant lounge.

Don't miss out on the fufú gnocchi or the steak churrasco for a flavorful experience. For a unique sweet treat to cap off your celebration, try the delicious coconut flan.

Mariel | 10 Post Office Sq., Boston, MA 02109 | $$$

Another remarkable birthday restaurant near Boston worth exploring is  Oleana . Its menu is a tribute to the culinary flavors of Turkey and the Middle East, with aromatic spices and fresh ingredients taking center stage. 

The wooden interior and modern feel of Oleana fit nicely with the sophisticated flavors of the dishes.

Don't miss the falafels, a specialty from the vegetarian meze section. For seafood lovers, you can't go wrong with the fried mussels.

Oleana | 134 Hampshire St., Cambridge, MA 02139 | $$

Established in 1992,  Artu has evolved from serving sandwiches and roasted meats to offering a wide array of Italian classics inspired by childhood in a Mediterranean clime. This Italian birthday restaurant in Boston is perfect for a gathering of friends. 

Artu stands out as a favorite among both locals and tourists, offering a warm and inviting family-first atmosphere in true Italian style.

The short rib ravioli and the classic burrata are truly, and equally, delicious.

Artu | 6 Prince St., Boston, MA 02113 | $

27. Atlantic Fish Company

If you're looking for a s eafood birthday meal,   Atlantic Fish has been serving Boston the freshest fish for decades, making it an excellent choice. It sources its fish directly from the harbor each morning and the chefs only buy what they expect to cook. Plus, the restaurant boasts a fantastic wine list to complement your dining experience.

If you're looking for sea-inspired things to do in Boston , this spot boasts a marine-themed interior and sidewalk seats, offering the perfect setting to dine outside on a bright summer's day.

Indulge in the delightfully fresh offerings from its raw bar, including caviar selections and cocktail seafood options such as Maine lobster, colossal crab and jumbo shrimp.

Atlantic Fish Company | 761 Boylston St., Boston, MA 02116 | $$$

Dining out at a birthday restaurant in Boston is a fantastic way to celebrate with friends and family, but there are other exciting options to consider as well. For example, cooking classes in Boston provide a fun and interactive way to spend quality time with loved ones while expanding your culinary skills. Alternatively, you can hire one of the many high-quality private chefs in Boston to bring the restaurant experience to the comfort of your own home. 

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With its diverse array of cuisines, locations and dining experiences, this list offers a glimpse into the vibrant and dynamic food scene that defines Boston. Whether you're searching for a lively spot for a celebratory gathering or a cozy venue for an intimate dinner, there's an option to suit every taste and occasion. 

So, what are you waiting for? Whether it's your own or a loved one's birthday for which you want to plan a special surprise, with these amazing birthday restaurants in Boston, you can start planning the perfect day with confidence.

For even more ways to explore Boston and beyond, check out other experiences happening on Cozymeal.

Discover the best in culinary experiences and products on Cozymeal: From in-person cooking classes to virtual cooking & mixology classes to private chef meals and top-rated cookware — from world-class chefs, mixologists & more.

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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!

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From Waiter to Guest at Nantucket’s Grande Dame Hotel

A writer returns to a classic Massachusetts hotel, where he worked 50 years ago, to ponder how he, the island, and the newly refurbished inn, have changed.

By Alexander Lobrano

Alexander Lobrano is a food and travel writer who has lived in France since 1986.

In the summer of 1974, I was working as a waiter at the White Elephant, the grande dame of Nantucket hotels, a rambling gray-shingled pile that sits right on the island’s harbor. One muggy August night, I sent the six lobster dinners ordered by Francis Sargent, the governor of Massachusetts and his guests crashing to the floor when some butter on the heel of my hand propelled my tray off the stand I’d been kneeling to set it down on. Thinking about it still makes me cringe.

I had not been back inside the White Elephant in almost 50 years when, last spring, I returned to the island to check into the famous inn as a guest, size up its recent multimillion dollar makeover at the hands of the Boston architectural firm Elkus Manfredi , and ponder the ways in which both the island and I had changed.

Though it’s hard to believe today, when Nantucket airport is filled with rows of private planes that have delivered their owners to this island 30 miles off the coast of Cape Cod, many people clucked at Elizabeth T. Ludwig’s hotel when it opened a century ago. Without the social cachet of more accessible resorts like Newport, R.I., or Saratoga Springs, N.Y., it struck many people as folly to believe the swell set would spend their holidays on Nantucket.

Ludwig defiantly named her hotel the White Elephant. The galloping popularity of the place meant she had the last laugh, too.

On a warm day in May, the island smelled the way it always had: a bracing scent of salt brine and peppery bayberry from the protected moors that cover most of its surface. On the way to the hotel, my cabdriver told me Nantucket had become too expensive, and I immediately noticed how much building there’d been. Still, I was amazed to see that the Chicken Box, a dive bar with live music and a pool table had survived.

When I’d arrived to work as a waiter, we’d been strenuously admonished by the maître d’ to avoid the Chicken Box, so of course we went there often. For me, it has always been a sort of shrine to the rough-and-ready character of the island, going back to the days when it teemed with sailors as a busy whaling port.

While the friendly front desk clerk photocopied my passport, I jokingly confided to a well-dressed man in a navy blazer that the last time I’d stayed at the White Elephant was when I’d lived in one of the staff dorms across the street.

He chuckled. “Would you like to see your old room again?” he asked. He handed me his business card: Kahled Hashem, President — General Manager, White Elephant Resorts. We agreed to meet after I had lunch at the Brant Point Grill, the hotel restaurant.

I ate delicious ceviche and a chicken katsu sandwich, which put the wilting plainness of the food I’d once served in the same dining room into relief. Popovers, foil-wrapped baked potatoes, steaks with black scoring from the grill, scrod with buttered breadcrumbs and Boston cream pie had vanished.

When the chef, Joseph Hsu, stopped by my table, he unpacked the inspiration for his menu. “Immigrant cooking often goes mainstream in the United States — look at how popular kimchi has become. It’s also true that Americans are a lot more gastronomically adventurous today than they were in the past,” he said.

Waiting for Mr. Hashem on the porch, I thought back to the summer I’d worked there.

On my first day, I’d been shown to a small room in a wooden dormitory with a window, a white-painted wooden dresser with swollen drawers, a single bed with a mattress that crunched when I sat on it and a clothing rail behind a mint-green shower curtain with three wire hangers.

After orientation, we had canned beef stew and instant mashed potatoes for dinner, then drank beer and smoked joints on the porch of our dorm. In the morning, my bed was filled with sand. It took a very puzzled minute or two to figure out that it had sifted through the cracks of my ceiling, which was the floor of the room above me. The rampant sex began once the staff had sized each other up. I went to the beach every day. It was a fantastic summer.

The new dormitory rooms astonished me. They had dorm-size fridges, microwave ovens and capacious built-ins. There was also a free staff laundry room, which reminded me of my hobo-like attempts to clean my work clothing — a white polyester short-sleeved shirt and black trousers — by soaking it in a bucket with shampoo (not advised).

After my tour of the dorms, Kelly Flynn, the rooms division manager, met me in the oak-floored, white-painted lobby. “Art is a major part of our renovation,” she said, gesturing at the striking mural of a woman in a row boat on the wall behind the front desk. It had been painted by the Israeli artist Orit Fuchs, as part of the hotel’s artist-in-residence program. “The idea is for the artists to produce a work that captures something of the essence of Nantucket or the hotel,” Ms. Flynn said.

During the renovation, she said, each of the hotel’s 54 rooms and 11 cottages was given its own design.

In addition to a color scheme derived from the island’s beaches, moors and surrounding sea, the grass cloth on the walls refers to local dune grasses. The thick custom-designed, blue-and-beige basket-weave, wall-to-wall carpeting in most rooms nods to Nantucket’s long craft tradition of basket-weaving, notably the beautiful Nantucket lightship baskets originally made by sailors.

Ms. Flynn also mentioned that the White Elephant now has a pool and showed me three of the 11 free-standing cottages. Very comfortably furnished, they are done in colors and wallpapers inspired by native plants of Nantucket, including bayberry and beach plum.

Afterward, walking into town on a red brick sidewalk, the sound of Spanish wafted from behind the thick privet hedges, as brigades of Mexican and Central American workers readied the historic homes hidden by this greenery for the season.

In town, I stopped at the Nantucket Whaling Museum , renovated in 2005, which offers a vivid presentation of the island’s whaling industry. It also has fascinating exhibits on the island’s history. One not to miss is “Island People: Portraits and Stories from Nantucket,” a collection of oil paintings, including “Nantucket Indian Princess,” an 1851 portrait of 11-year-old Isabella Drapper, an islander of mixed Wampanoag and African American heritage, by Hermine Dassel, which attests to the island’s historic diversity.

After the museum, I went on an urgent mission. I wanted, no, needed, a lobster roll. I asked the carpenter who was repairing the door jamb of the Club Car, a bar in an old rail car that had been another off-hours favorite of White Elephant staffers, where to go. He grinned. “You’re in luck, my friend. There’s a wicked good one four doors down.”

B-ackyard BBQ is what used to be known as a Townie bar, offering relief from the tweeness of so many other places downtown. It also just happened to serve a generously filled beauty of a lobster roll, crowned with a gild-the-lily garnish of crunchy onion rings. It was perfect succulence, but at $42.00, hardly a workingman’s lunch. Never cheap, Nantucket has become a vertiginously expensive destination.

Driving the island the following day, I was relieved to find most of it still wild but shocked to see the eroded beaches at Tom Never’s Head and Siasconset, the village where a friend and I picnicked on overstuffed smoked turkey sandwiches from Something Natural , an island bakery and sandwich shop.

Nantucket today is a much more joyously cosmopolitan place than it was in the ’80s, when most summer visitors came from nearby Boston, Providence, R.I., and Hartford, Conn., and the staff was filled with college kids like me.

Today, few Americans are among the seasonal employees. Mr. Hashem, himself an Egyptian American from Houston, said that people from more than 20 countries work at the resort, with a large number from the Caribbean and Eastern Europe. My cabdriver was Greek. The chef, Mr. Hsu, is a Chinese-Hawaiian American from Pennsylvania, and my waiter at the White Elephant was Slovenian. “This summer I am here on an H2-B visa,” he told me when we started chatting. “But I want to come back for good.”

The starting rate for a standard room at the White Elephant is $395 in spring; $995 in summer and $395 in fall.

Follow New York Times Travel on Instagram and sign up for our weekly Travel Dispatch newsletter to get expert tips on traveling smarter and inspiration for your next vacation. Dreaming up a future getaway or just armchair traveling? Check out our 52 Places to Go in 2024 .

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Watch Sting begin 2024 tour in Germany with Police hits and deep cuts

The rock veteran kicked off his ‘Sting 3.0’ tour by unearthing songs not performed in decades

Sting has kicked off his ‘Sting 3.0’ tour – which sees him performing in a trio set-up across Europe and the US. The rock veteran performed its first date in Dresden, Germany at the Dresdner Musikfestspiele.

• READ MORE: In praise of ‘The Traitors’ and its terribly brilliant cover songs

The ‘Sting 3.0’ tour features Sting performing alongside guitarist and longtime collaborator Dominic Miller and drummer Chris Maas, the latter previously serving as touring drummer for Mumford & Sons .

In Dresden on May 25, the setlist consisted of an almost even split between solo material and songs written and performed with the Police . It began with his former band’s ‘Voice Inside My Head’, performing it for the first time since 2006, as Consequence notes.

Other songs that made a comeback into Sting’s live repertoire include the Police’s ‘Synchronicity II’ (since 2018) and ‘Tea in the Sahara’ (since 2017), along with Sting’s own ‘When the Angels Fall’ (since 1992) and ‘Never Coming Home’ (since 2012).

Alongside these deep cuts were fan favourites like ‘Roxanne’, ‘Desert Rose’, ‘Fields of Gold’, and ‘Every Breath You Take’. See fan footage of that night, along with Sting’s forthcoming tour dates below.

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Sting’s setlist for the ‘Sting 3.0’ tour in Dresden, Germany (via Setlist.fm ):

‘Voices Inside My Head’ ‘Message In A Bottle’ ‘Synchronicity II’ ‘Driven To Tears’ ‘Fields Of Gold’ ‘Never Coming Home’ ‘When The Angels Fall’ ‘A Thousand Years’ ‘Tea In The Sahara’ ‘The Hounds Of Winter’ ‘Mad About You’ ‘Fortress Around Your Heart’ ‘Can’t Stand Losing You’ ‘Englishman In New York’ ‘Shape Of My Heart’ ‘Walking On The Moon’ ‘So Lonely’ ‘Desert Rose’ ‘King Of Pain’ ‘Every Breath You Take’ ‘Roxanne’ ‘Fragile’

Sting will continue his tour through Europe this week onwards till early August, covering Ireland, Croatia, Slovenia, Budapest, Poland, among others. These dates will see him and his band perform in arenas and festivals.

However, his ‘Sting 3.0’ US tour – which begins there on September 17 – promises performances in far more intimate venues, such as The Fillmore Detroit and Los Angeles’ The Wiltern, alongside co-headlining engagements with Billy Joel . See his full tour itinerary below.

Sting’s ‘Sting 3.0’ tour dates are:

MAY 27 – Zagreb, Croatia, Zagreb Arena 29 – Ljubljana, Slovenia, Arena Stozice 31 – Budapest, Hungary, Budapest Arena

JUNE 01 – Bratislava, Slovakia, TIPOS Arena 04 – Plzeň, Czech Republic, Amphitheatre Lochotín 06 – Gdańsk, Poland, Ergo Arena 07 – Łódź, Poland, Atlas Arena 09 – Kaunas, Lithuania, Zalgirio Arena 10 – Tartu, Estonia, Tartu Song Festival Grounds 14 – Cheshire, UK, Delamere Forest 16 – Plymouth, UK, Plymouth Summer Sessions 18 – Cork, Ireland, Musgrave Park 19 – Belfast, UK, Belsonic (Ormeau Park) 22 – Suffolk, UK, Thetford Forest 23 – Nottinghamshire, UK, Sherwood Pines 25 – Fontainebleu, France, FBLO Festival

JULY 05 – Athens, Greece, Odeon of Herodus Atticus 06 – Athens, Greece, Odeon of Herodus Atticus 10 – La Rochelle, France, Les Francofolies 11 – Brive, France, Lovely Brive Festival 12 – Carhaix, France, Vieilles Charrues Festival 14 – Rotterdam, Netherlands, North Sea Jazz Festival 16 – Toulon, France, Esplanade Zenith Toulon 17 – Montreux, Switzerland, Montreux Jazz Festival (Lake Stage) 19 – Nieuwpoort, Belgium, Beach Festival 20 – Fulda, Germany, Fulda Domplatz 23 – Salem, Germany, Schloss Salem 24 – Füssen, Germany, Barockgarten am Festspielhaus 27 – Lingen, Germany, Platz vor der Emsland Arena 28 – Stuttgart, Germany, jazzopen 30 – Carcassonne, France, Festival de Carcassonne

AUGUST 01 – Corsica, France, AIO Festival 03 – S.ta Margherita di Pula (CA), Italy, Forte Arena 31 – Aspen, Colorado, Aspen Snowmass

SEPTEMBER 17 – Detroit, Michigan, Fillmore Detroit 18 – Detroit, Michigan, Fillmore Detroit 20 – Toronto, Ontario, Massey Hall 21 – Toronto, Ontario, Massey Hall 24 – Toronto, Ontario, Massey Hall 27 – St. Louis, Missouri, Busch Stadium % 30 – Philadelphia, Philadelphia, The Met

OCTOBER 01 – Philadelphia, Philadelphia, The Met 04 – Boston, Massachusetts, MGM Music Hall, Fenway Park 06 – Boston, Massachusetts, MGM Music Hall, Fenway Park 07 – Brooklyn, New York, Brooklyn Paramount 09 – Brooklyn, New York, Brooklyn Paramount 10 – Brooklyn, New York, Brooklyn Paramount 12 – Port Chester, New York, The Capitol Theatre 15 – Washington, DC, MGM National Harbor 16 – Washington, DC, MGM National Harbor 20 – Miami, Florida, Fillmore Miami Beach 21 – Miami, Florida, Fillmore Miami Beach 22 – Atlanta, Georgia, Cobb Energy Performing Arts Centre (CEPAC) 25 – San Antonio, Texas, Alamodome % 28 – Chicago, Illinois, Auditorium Theatre 29 – Chicago, Illinois, Auditorium Theatre

NOVEMBER 01 – Chicago, Illinois, Auditorium Theatre 06 – San Francisco, California, The Masonic 07 – San Francisco, California, The Masonic 09 – Las Vegas, Nevada, Allegiant Stadium % 12 – Los Angeles, California, The Wiltern 13 – Los Angeles, California, The Wiltern 15 – Los Angeles, California, The Wiltern

% with Billy Joel

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