Top Boston Cruises &amp; Sailing

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore the world-famous Boston Harbor and see the city’s historic sites while listening to live commentary on board, from tales of the Revolutionary War to local legends. While you cruise, enjoy views of the city skyline as well as the Boston Harbor Islands, USS Constitution (“Old Ironsides”), and the Bunker Hill Monument.

City Cruises Boston Historic Sightseeing Harbor Cruise

1 hourFree Cancellation

Likely to Sell Out

City Cruises Boston Whale Watching Cruise by High-Speed Boat

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed boat in Boston that gets to and from the whales in the least amount of time possible. Look out for humpback and fin whales, plus Atlantic white-sided dolphins, with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.

City Cruises Boston Whale Watching Cruise by High-Speed Boat

3 hours 30 minutesFree Cancellation

4.5

(3 398)

from US$86

Boston Harbor Sightseeing Cruise

Enjoy unparalleled views of the Boston Harbor from the water during this 90-minute sightseeing cruise. Set sail aboard a classic tall-ship schooner. Enjoy plenty of time to ask the captain and crew about local landmarks and Boston’s history. You'll also have plenty of time to relax. Soft drinks and alcoholic beverages are available to purchase, including several beers brewed right in South Boston.

Classic Tall Ship Cruise in Boston Harbor

1 hour 30 minutes to 2 hoursFree 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 Duck Boat Sightseeing City Tour with Cruise

1 hour 20 minutesFree Cancellation

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Boston Harbor Narrated Sunset Cruise

Sightseeing Day Sail around Boston Harbor

1 hour 30 minutes to 2 hoursFree Cancellation

Boston Harbor Sunset Sail Tour

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

(203)

from US$133

City Cruises Boston: Signature Dinner Cruise

2 to 3 hoursFree Cancellation

Boston Ghosts and Gravestones Trolley Tour

City Cruises Boston Signature Lunch Cruise

4.3

(144)

from US$83

Cruise through Boston Harbor on the Yacht Patriot, a modern take on a 1920s yacht, for an intimate 1.5-hour cruise. We offer a daytime narrated tour, that allows guests to dive into the rich history of Boston as a local guide highlights key landmarks like the USS Constitution, Bunker Hill Monument, and the historic waterfront. We also offer a non-narrated sunset cruise option that will cruise by the USS Constitution to watch the cannon fire at sunset. Both experiences offer unobstructed views and a relaxing atmosphere away from the city's hustle.

Boston Harbor Cruise Aboard Yacht Patriot

Boston Harbor Cruise Aboard Yacht Patriot

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

Boston Harbor Moonlight Cruise

New England Fall Lunch Cruise in Boston Harbor

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 13 Stops

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

Boston Holiday Cocoa Cruise

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

Boston Harbor Night Cruise

1 hourFree Cancellation

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Top Attractions in Boston

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Attractions

Boston North End

What are people saying about Boston

Lexington and Concord 3 hour private car tour from Boston

Lavonna_D, Sept 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 Brunch Cruise

Suzanne_B, Sept 2026

Brunch tour was excellent.

The brunch food was so good and fresh with many healthy options. The beautiful boat was clean and well maintained and felt very safe. The crew was very sweet. The views of the harbor were amaing. So many boats to see. I would have gone for dinner too if it wasn't sold out. It was a great experience. The captain was sweet and the tour guide was both informative and soothing. The bartender was very informative and nice. Thank you for the tour.

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! :)

Boston Harbor Sunset Sail Tour

Cameron_D, Aug 2026

Great sail aboard the...

Great sail aboard the Adirondack. The ship is beautiful and smaller than the large party-style cruises we saw cruising around at the same time. There were a good number of people on board, but we did not feel cramped for a Wednesday evening sunset ride. Hannah answered all our questions about the boat, the harbor, and even snapped a great picture of us as we celebrated our anniversary! Thanks!

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!

Private 4-Hour Driving & Walking City Tour

Clinton_E, Mar 2026

Outstanding overview of Boston!

We thoroughly enjoyed our 4-hour Boston overview with an amazing guide, Neal! The tour was a well-balanced mix of walking and riding. We saw so much in 4 hours! Neal clearly has a passion for his city, and this made for a fun, interesting, and educational experience. Even though I have been on a few tours of Boston in the past, he still introduced us to several new sites and many new facts! He recommend several great restaurants that we would have never have explored if not for him. Ask him for some “cash only” recs!

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

Liliana_S, Dec 2025

Family-Friendly Holiday Cruise

We had a wonderful time on the Boston Holiday Cocoa Cruise! The whole vibe was so festive and relaxed, with amazing holiday music that really set the mood. The yacht itself was decorated beautifully, cozy, cheerful, and perfect for families. We mostly just had snacks, so I can’t speak much to the food, but the drinks were fantastic. The staff was super friendly and welcoming. The highlight for us was definitely the view. The Boston skyline at night from the water is just breathtaking. I’d definitely recommend this cruise, It’s festive cheer, gorgeous scenery, and a relaxed atmosphere.

Private Boston, Lexington & Concord Historical Tour

Amanda_M, Oct 2025

Fun, educational and custom tailored for us

I’ve been on numerous group tours, but this was our first private tour as a couple. We loved that it was tailored to our interests and not your typical group tour that tries to cater to everyone’s interests. Our guide, Curtis, is very knowledgeable on history of the area and we learned a lot while getting not only historical information but asking the questions we wanted to know. It was a great tour and a wonderful addition to our trip!

Boston Sightseeing Tour - a fully-narrated driving tour

Patricia_C, Oct 2025

The Best Way to See Boston

I booked the 3-hour private driving tour in Boston, and from start to finish it was unforgettable — all thanks to our guide, Peter. From the moment we were picked up at the cruise port, it was clear we were in good hands. The van was spotless, comfortable, and climate-controlled. Peter’s punctuality and friendliness instantly put us at ease. As we rolled through Boston’s neighborhoods — Back Bay, Beacon Hill, the South End — Peter seamlessly wove together stories, historical context, and fun anecdotes. He navigated tight streets like a pro, making sure we caught striking views (and photo stops) without compromising the itinerary. His knowledge is seemingly bottomless: he referenced dates, personalities, lesser-known tales, and surprised us with this fun facts. We passed by so many iconic sites: the Paul Revere House, Old North Church, the USS Constitution, Bunker Hill, Faneuil Hall, Copley Square, Fenway Park, Harvard, MIT, and more. None of that felt like mere “drive-by” narration — Peter made each landmark come alive through storytelling. He has a warm, inviting personality — we felt like we were touring with a knowledgeable friend rather than a guide “on duty.” His passion for Boston is infectious! By the end we walked away feeling like insiders, not just tourists. In short: Peter exceeded every expectation. If you visit Boston (even for just a few hours), book this tour. You’ll see the city, yes—but more importantly, you’ll feel the city, through stories, context, and heart. We will remember this tour for years to come — thank you, Peter!

New England Fall Lunch Cruise in Boston Harbor

Dottie_J, Oct 2025

Wonderful Cruise

What wonderful lunch cruise. The captain gave us information about local history while we gently cruised around Boston Harbor! The food on the buffet was excellent with roasted pork loin, turkey, butternut squash ravioli, salad, saffron rice, garlic rolls, and brownies. Everything was delicious! My husband and I enjoyed this very much. The crew were also very nice and professional. When we finished eating, there were still all the sights to see. This a must do on a Boston visit!