Top Boston Cruises &amp; Sailing

Boston Harbor Sunset Cruise

(647)

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.

from $54

City Cruises Boston Historic Sightseeing Harbor Cruise

4.5

(1,396)

1 hourFree Cancellation

from $46

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

3.7

(163)

2 to 3 hoursFree Cancellation

from $133

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

4.7

(617)

1 hour 30 minutes to 2 hoursFree Cancellation

from $40

Boston Harbor Sightseeing Cruise

4.5

(198)

Boston Harbor Narrated Sunset Cruise

from $46

4.2

(537)

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.

from $29

City Cruises Boston Whale Watching Cruise by High-Speed Boat

4.4

(3,115)

3 hours 30 minutesFree Cancellation

from $86

4.4

(412)

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

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.

from $56

Boston Harbor Brunch Cruise

(145)

from $106

Boston Harbor Sunset Sail Tour

4.8

(132)

from $82

Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River

(9,579)

1 hour 20 minutesFree Cancellation

from $62

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this public sail is a perfect outing for family and friends. All ticket proceeds contribute to the World Ocean School's educational programs, ensuring a meaningful experience on the water. Enjoy an enriching day while supporting maritime and experiential education.

Harbor Sail Aboard the Tall Ship Denis Sullivan

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.

from $55

Boston Hop-On Hop-Off Trolley Tour with 13 Stops

4.3

(5,620)

from $52

Sightseeing Day Sail around Boston Harbor

4.8

(542)

1 hour 30 minutes to 2 hoursFree Cancellation

from $67

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

4.7

(2,579)

1 hourFree Cancellation

from $36

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

(414)

Discover the New Hampshire and Maine coasts, plus the highlights of Kennebunkport, all in one day: this private, full-day tour from Boston makes exploring easy. Meet your guide in the morning at your departure point, and hop aboard your private van. You'll stop in the historic town of Portsmouth, will discover the Cape Neddick Nubble Lighthouse, can tour the President Bush Compound at Kennebunkport, and upgrade to add on a lobster tour.

from $81

Boston to Kennebunkport with Optional Lobster Tour

4.8

(44)

8 to 10 hoursFree Cancellation

from $125

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

1489

from $51

City Cruises Boston: Signature Dinner Cruise

4.0

(301)

2 to 3 hoursFree Cancellation

from $119

4.0

(198)

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

Cruise Boston Harbor aboard a luxury yacht, complete with superb city views and a buffet brunch featuring both breakfast and lunch offerings. For 2-hours you'll explore the waters from Rowes Wharf to the Charlestown Naval Yard and back, sailing past sights such as Castle Island and Boston Light. Spend some time enjoying the yacht's three climate-controlled decks or dancing to the sounds of a live DJ mix.

from $52

City Cruises Boston Premier Brunch Cruise on Odyssey

4.5

(28)

City Cruises Boston Premier Lunch Cruise

from $104

4.3

(7)

Explore Boston on a trolley tour that’s timed to catch sunset over the Charles River. Many Boston sites are illuminated—and uncrowded—at night, making this an ideal time to explore Boston Harbor, Cambridge, the Public Garden, and more. Live narration from an experienced guide showcases the stories and culture behind each place you visit, from stylish seaside neighborhoods to revolutionary war–era landmarks.

from $107

Boston Summer Nights Trolley Tour plus River Cruise

4.4

(145)

from $51

Dog Day of Summer Harbor Cruise in Boston

4.9

(8)

Boston Holiday Cocoa Cruise

from $28

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Top Attractions in Boston

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Attractions

What are people saying about Boston

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.

Beacon Hill Boston Walking Tour | History + Fun Photo Tips

Amy_K, Oct 2025

Lovely time in Beacon Hill

Saba is a delightful host for the Beacon Hill neighborhood. She has been giving tours for 20 years or so, and knows the back stories of the area. She gave us some great tips on how to photograph the area and our pictures are gorgeous! If you are interested in learning things about Beacon Hill that are not in the guidebooks, and you want to come away with some beautiful photographs, this tour is for you.

Boston Architecture + History Walking Tour | Fun Photo Tips

Irina_Y, Oct 2025

A gem

It was an absolutely delightful experience, like walking with a friend who shares their favorite gems in the city with you. Saba is a fantastic guide, very knowledgeable and wonderful to learn from. She gave many tips how to improve photos and I have a great collection of photos now. Thank you, Saba, for a wonderful experience!

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!

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

Leah_C, Aug 2025

Must do!

This was such a fun, informative and beautiful end of the day activity! The tour guide was knowledgeable, friendly and the perfect person for this job. The city views were breathtaking and the sunset just added to the experience. I can’t recommend this enough. If we return to Boston, which we will, this will be back on our list!

Boston Private City Tour and Chauffeur Service

Ingrid_D, Aug 2025

Touring Boston with our Siblings

My husband and I traveled to Boston via train with our sisters the weekend of August 22. One of our activities was a four hour private tour of Boston. We had a fantastic time with our guide/driver, Sam! Sam was very professional and knowledgeable and arrived at our hotel at the designated time. He also allowed us to get out of the vehicle to take photos numerous times. I definitely recommend this particular tour of beautiful Boston, MA! It’s an experience we’ll never forget. Thanks again, Sam!

Lexington and Concord 3 hour private car tour from Boston

David_C, Aug 2025

Really Enjoyable Experience

Our guide, Christian, was very informative and really pleasant. We really enjoyed how he related the experience to us. Picked us up at our hotel and dropped us off at the place of our choice. I would definitely recommend this tour to anyone interested in learning more about Lexington and Concord.

Boston to Kennebunkport with Optional Lobster Tour

Caren_C, Jun 2025

This is a must do Excursion. Lovely Matt, history galore!

Matt was outstanding. Very personal and knows his history. Absolutely would do this Excursion again. He was so great we took 2 other Excursions with him. He is fantastic and what an addition to the beauty of the New England states. This is a must do!!!!