Top Boston Cruises &amp; Sailing

City Cruises Boston Historic Sightseeing Harbor Cruise

1 hourFree Cancellation

Boston Duck Boat Sightseeing City Tour with Cruise

1 hour 20 minutesFree Cancellation

See Boston from a whole new angle aboard a Boston Harbor evening cruise. Watch the sunset from the water, and glide out to the Old North Church and Historic Site, the Charlestown Navy Yard, the USS Cassin Young, and more. As a bonus, listen to the cannon fire of the USS Constitution, which marks the sunset each night, and sip a cocktail (own expense) from the onboard bar as you relax and enjoy the views.

Boston Harbor Sunset Cruise

Boston Harbor Sunset Sail Tour

Boston Harbor Sightseeing Cruise

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

Relive one of the most important events leading up to the American Revolution and learn about a side of the story most tourists miss on this guided tour of the Boston Tea Party Ships and Museum. Explore authentically restored tea ships with the help of a guide as you get their insights into this pivotal event, and throw some of your own tea into Boston Harbor. It's an ideal experience for American history buffs, tourists, and locals alike.

Boston Tea Party Ships and Museum Admission

1 hourFree Cancellation

Try a unique alternative to a typical night out in downtown Boston with an exciting dinner cruise along the city’s waterfront. This expedition on Boston Harbor features a meal with live entertainment and dancing. Watch the sun set, then take a stroll under the stars and enjoy the view of the illuminated Boston skyline at night, or head to the dance floor for music and fun in the ship’s nightclub.

City Cruises Boston Premier Dinner Cruise on Odyssey

2 to 3 hoursFree Cancellation

3.8

(205)

from $138

Special Offer

Boston: Freedom Trail History Small Group Walking Tour

2 hours 30 minutesFree Cancellation

Boston Holiday Cocoa Cruise

Sightseeing Day Sail around Boston Harbor

1 hour 30 minutes to 2 hoursFree Cancellation

Boston Harbor Moonlight Cruise

Discover a whole new side of baseball history with the help of a guide on this tour of Fenway Park, one of baseball’s most beloved stadiums. Revisit the careers of Red Sox greats like Ted Williams, Babe Ruth, and Carl Yastrzemski, celebrate the club’s numerous World Series titles, and tour famous stadium locales like the ‘Green Monster,’ ‘Pesky’s Pole,’ and the Fenway Park Living Museum. It’s ideal for baseball fans, be they locals or tourists.

Tour of Historic Fenway Park, America's Most Beloved Ballpark

1 hourFree Cancellation

Enjoy a gourmet brunch on this scenic cruise of the Boston Harbor. Set sail aboard the Northern Lights at Rowes Wharf and settle in for a buffet filled with eggs, bacon, fresh fruit, and more. View popular Boston highlights such as Bunker Hill Monument, the USS Constitution, Old North Church, and Sea Castle Island. This brunch cruise offers a great overview of Boston and a lovely morning on the water.

Boston Harbor Brunch Cruise

Enjoy one of the simplest ways to discover Martha's Vineyard, and leave all the planning and logistics to someone else, on this hassle-free day trip from Boston. Following pickup directly from your centrally located hotel, take a short ferry ride to Martha's Vineyard. Upon arrival, enjoy free time to explore—or upgrade to add on an island tour that visits its highlights. Complimentary snacks, bottled water, and guidebooks are provided during the drive.

Boston to Martha's Vineyard Day Trip with Optional Island Tour

12 hoursFree Cancellation

Explore the best of Boston at your own pace on a hop-on hop-off trolley tour of the city. Choose from a 1- or 2-day pass and see Boston’s top attractions, including the USS Constitution, the original bar from TV show “Cheers,” and the Faneuil Hall Marketplace, to name a few. The pass includes discounted admission to the Boston Tea Party Ships and Museum, to enjoy during or after the tour.

Boston Hop-On Hop-Off Trolley Tour with 11 Stops

1 hour 45 minutesFree Cancellation

Likely to Sell Out

City Cruises Boston Signature Lunch Cruise

4.3

(144)

from $81

Boston Shore Excursion: Boston Hop-On Hop-Off Trolley Tour

1 hour 45 minutesFree Cancellation

1 hour to 1 dayFree Cancellation

Boston Ghosts and Gravestones Trolley Tour

Private Day Trip to Lexington and Concord from Boston

6 hours 30 minutesFree Cancellation

Price varies by group size

For anyone thinking of attending Harvard, or for those who simply want a glimpse of college life at the famous university, this tour is a must. Get an exclusive account from current Harvard students, who provide key insights into the life and times at Cambridge with a theatrical, humorous flair. Check out the old buildings at Harvard Yard and Harvard Square and learn about the school’s storied past. Illustrated map of Harvard Square included. Choose from several departure times throughout the day.

Harvard University Campus Guided Walking Tour

1 hour 10 minutesFree Cancellation

Enjoy a private pickup and ride to historic Salem with your guide. Walk the streets where hysteria once ruled, and learn about the Puritan past that shaped daily life in early New England. Uncover the tragic history of the witch trials during a visit to the moving Witch Trials Memorial. Discover Salem's prosperity during the "Old China Trade," when ships sailed to Asia and returned with exotic goods like silk and porcelain, making it one of the wealthiest towns in the early United States and home to the country's first millionaire. See how this era shaped the city beyond the witch trials with a visit to the Salem Maritime National Historic Site. You'll have 1.5 hours of free time to grab lunch and browse for souvenirs, from classic mementos to mystical finds like tarot decks and potion ingredients. Afterward, we'll continue exploring Salem's landmarks before your private ride returns you to Boston.

Salem Full Day Private Tour from Boston

8 hoursFree Cancellation

Price varies by group size

Boston Private 3-Hour Tour by Car

3 hoursFree Cancellation

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Must-Dos in Boston

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What are people saying about Boston

Private Boston, Lexington & Concord Historical Tour

Fran_K, Oct 2026

The Revolution Clarified

This tour was excellent. Our guide drove us throughout Boston, pointing out historical references, weaving the story of the Revolution as he took us to Lexington and Concord. There were a few contemporary places on the itinerary we were not interested in so the tour was not as long as it could have been but we were more than satisfied overall.

Boston Private 3-Hour Tour by Car

Rebecca_S, Sep 2026

Christian, #1 tour guide

If you want to see Boston with a 3-Hour Tour by car, I would recommend using this company. Our tour guide, Christian, was polite, considerate of our requests on the trip, and extremely knowledgable regarding all aspects of Boston history. Joan, handling our tour request, was fast getting back to me regarding tour time options and making arranging that insured our tour easy and enjoyable.

Lexington and Concord 3 hour private car tour from Boston

Lavonna_D, Sep 2026

Informative and interesting.

Great tour! Our guide, Christian, was interesting and informative as he lead us back in time to the day the American Revolutionary War started in Lexington and Concord. As a retired history teacher he really knew what he was talking about. Interesting to listen to and follow. The 4 of us had a great day. The drive is beautiful too as you drive in the countryside of Lexington and Concord. I would highly recommend!

Boston Harbor Sunset Sail Tour

Cheryl_M, Sep 2026

What a great experience!

I booked this at the last minute and was so glad I did. The crew was great, kind and knowledgeable. The weather was perfect and the view from the boat was extraordinary at sunset. It was so nice to be with a small group of people rather than a large boat.

Private City Tour of Boston and Cambridge

Lindsay_B, Aug 2026

Great Day in Boston with BJ!

This tour definitely exceeded my expectations! We had 3 generations of travelers from ages 7-79 and everyone really enjoyed it. It was all of our our first time in Boston and this was a great activity for our first day. We had BJ as our guide and he communicated with me in advance of the tour and picked us up timely at our hotel. Our first stop was an Italian coffee/pastry shop in the North End. There we talked through a loose plan for the day, but the best thing about this tour was that BJ was totally flexible… There were certain places we wanted to spend more time, and BJ accommodated us, provided interesting commentary and even helping entertain the kids when one was bored and the rest of us were taking a little longer at a site/exhibit. His vehicle was clean, fully functioning and he had parking passes at certain key places allowing us to pack a lot into one day. I would definitely recommend this tour and BJ to anyone visiting Boston! We will talk about this day and the places we visited for years to come. Already want to plan a return trip! :)

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

Lisa_S, Aug 2026

Beautiful sunset cruise....

Beautiful sunset cruise. Got to see planes flying overhead. Saw the skyline of the city from a different perspective than on land. The tour guide was very informative. Bathrooms and beverages for purchase onboard. Recommend getting there early to get in line for a better seat.

Boston Harbor Brunch Cruise

Stacey_M, May 2026

Good food and a Great Experience!

My boyfriend and I truly enjoyed this Brunch/Harbor Cruise. It was, sadly, a rainy day but there is full capacity indoor seating so not to worry, we stayed warm and dry. They way the tables are set up, you can see great from any one of them but we got a great table at the front of the boat. The ship's captain narrates all points of interest and though I practically live in Boston, I still gleaned some new details that I did not already know about some of them. The crew was friendly, accommodating and knowledgeable. There was MORE than enough food for everyone on board and I found the food to be fairly decent enough for a brunch cruise (I mean, it's not a 5 star resort, it's a BOAT) with plenty of variety of foods and everything was tasty and seemingly fresh. I will add that I bought my tickets through Viator last minute because I didn't want to miss out but there were plenty of tickets available at the dock and they were about half the price.

Private Luxury Transportation to/from Boston Logan Airport (BOS)

Cassie_W, Apr 2026

Great communication and quality transportation!

Our flight had several delays throughout the day, but I was able to stay in communication with them and they watched the flight updates for changes. Our driver, Eric, was helpful and friendly, even though our flight arrived at midnight. We were so grateful to have him ready for our arrival!

Salem half day private tour from Boston

Joan_A, Mar 2026

Fantastic tour!

If you’re visiting Salem, do yourself a favor and take a tour with Martin. Our experience was absolutely fantastic and easily one of the highlights of our trip. Martin led a guided tour of Salem that was both incredibly informative and genuinely entertaining. He showed us six filming locations from Hocus Pocus, which was a really fun addition, and also brought us to the iconic Bewitched statue. Beyond the pop culture stops, his in-depth knowledge of the Salem Witch Trials was impressive—he explained the history in a way that was engaging, thoughtful, and easy to understand. He also made a stop at the oldest candy shop in the United States, which was such a unique and memorable part of the tour. It’s clear Martin truly knows Salem inside and out. What really set the experience apart, though, was how much he went above and beyond. At the end of the tour, he even helped us secure reservations at a restaurant so we could relax and enjoy the rest of our evening without worrying about finding a place to eat. Martin clearly cares about making sure people have a great experience in Salem (and other areas in and around Boston), and it shows in every part of the tour. If you’re looking for a guide who is knowledgeable, personable, and passionate about the history of the area, Martin is the one to go with. Highly recommend!

Boston Holiday Cocoa Cruise

Jude_B, Dec 2025

Romantic and silly date night

Food was honestly so-so, but the drinks were absolutely delicious. The music was great, decor was beautiful, and staff were all obviously having a great time. The view and ride was amazing as well. Being able to step out onto the deck, even though it was cold, to get a perfect view of the skyline was amazing. Thanks for an unforgettable date!

3-Hour Private "Cold Weather- Warm Van" Driving Tour of Boston

Giulio_M, Dec 2025

The absolute best way to see Boston—Peter is a legend!

If you are looking for the perfect way to see Boston without battling the freezing temperatures, this is it. Our group of four booked this tour on a whim, and it ended up being the highlight of our trip. The 'warm van' promise was fully kept, but the real star of the show was our guide, Peter. I cannot speak highly enough of him. Often, a three-hour drive can feel long, but Peter kept our attention the entire time. He has an endless supply of fascinating stories and local history that you simply wouldn't get from a guide book. He managed to make the city come alive while we stayed perfectly comfortable. If you want a tour that feels personal, engaging, and incredibly comfortable, ask for Peter. Worth every cent!