Top Boston Cruises &amp; Sailing

Boston Harbor Sunset Cruise

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.

(661)

from $54

City Cruises Boston Whale Watching Cruise by High-Speed Boat

3 hours 30 minutesFree Cancellation

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.

(3,115)

from $86

Classic Tall Ship Cruise in Boston Harbor

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(622)

from $40

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

3.7

(167)

from $133

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

4.5

(1,408)

from $46

Boston Harbor Sunset Sail Tour

Boston Harbor Sightseeing Cruise

4.8

(138)

from $82

Special Offer

Boston: Freedom Trail History Small Group Walking Tour

Special Offer

2 hours 30 minutesFree Cancellation

4.9

(6,794)

from $39

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

(412)

from $56

(414)

from $81

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 Harbor Narrated Sunset Cruise

(149)

from $106

Boston Duck Boat Sightseeing City Tour with Cruise

4.2

(541)

from $29

1 hour 20 minutesFree Cancellation

Sightseeing Day Sail around Boston Harbor

(9,597)

from $62

Special Offer

1 hour 30 minutes to 2 hoursFree Cancellation

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

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.

5.0

(1)

from $51

Boston Tea Party Ships and Museum Admission

1 hourFree Cancellation

4.7

(2,605)

from $36

City Cruises Boston: Signature Dinner Cruise

2 to 3 hoursFree Cancellation

4.0

(301)

from $114

"Embark on a private day trip from Boston to Plymouth, MA, and delve into the profound history of one of New England's most important locales. Begin your journey at Pilgrim Memorial State Park, where the storied Plymouth Rock marks the Pilgrims' landing. Aboard the Mayflower II, a detailed replica, learn about the 1620 voyage. The Plimoth Patuxet Museums offer a lively reenactment of 17th-century life; engage with costumed interpreters and savor a traditional meal at the café. Discover the Pilgrim Hall Museum, the nation's oldest public museum, featuring an array of real Pilgrim artifacts. Stroll along Plymouth Harbor for beautiful views. The tour concludes at the towering National Monument to the Forefathers, before allowing some free time to explore downtown Plymouth's charming shops, galleries, and cafes. This tour not only traces the historical tapestry of Plymouth but also offers a deeply personal connection to America’s foundational stories."

Private Boston Day Trip to Plymouth MA

9 hoursFree Cancellation

4.5

from $1,090

Per group

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.

Boston Summer Nights Trolley Tour plus River Cruise

(145)

from $53

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.

City Cruises Boston Premier Brunch Cruise on Odyssey

4.5

(28)

from $104

Boston Harbor Night Cruise

1 hourFree Cancellation

Boston Ghosts and Gravestones Trolley Tour

(14)

from $46

(2,472)

from $47

Dog Day of Summer Harbor Cruise in Boston

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.

4.9

(8)

from $28

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

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

4.3

(5,665)

from $52

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Top Attractions in Boston

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Attractions

What are people saying about Boston

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 Walking and Driving 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 City Tour of Boston, Lexington, and Concord

James_S, Oct 2025

Great way to see Boston and area in a short time!

Although this is not the cheapest way to see the Boston area, it is by far the best if you want to see a maximum amount in a minimum time in great comfort! It was just myself and my husband for 6 hours, but it would be cheaper if you have more people to split the cost. Being chauffeured around by Sam was wonderful! He is so affable, knowledgeable and flexible and made our tour a total pleasure! He picked us up and returned us to our Waltham suburban Boston hotel which was very convenient. You can arrange this tour to your liking and stay at any given place as much or as little as you like. I highly recommend this tour and ask for Sam!

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!

Boston Harbor Sunset Sail Tour

Kathryn_h, Sep 2025

Beyond our expectations

Beyond our expectation - the sunset cruise takes you to the parts of the harbor that have spectacular views. Planes landing at Logan airport was a sight to behold as they flew over head. The crew were engaging and knowledgeable and added some history and insight to points of interest. Highly recommend!

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!

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!!!!