Top Boston Cruises &amp; Sailing

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.

4.3

(464)

from $56

Likely to Sell Out

City Cruises Boston Whale Watching Cruise by High-Speed Boat

City Cruises Boston Whale Watching Cruise by High-Speed Boat

3 hours 30 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.

(3,316)

from $86

Boston Harbor Sunset 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.

(719)

from $54

Classic Tall Ship Cruise in Boston Harbor

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(768)

from $40

Boston Harbor Sunset Sail Tour

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.

4.8

(168)

from $82

City Cruises Boston Historic Sightseeing Harbor Cruise

City Cruises Boston Historic Sightseeing Harbor Cruise

1 hourFree Cancellation

Boston Duck Boat Sightseeing City Tour with Cruise

(1,488)

from $46

1 hour 20 minutesFree Cancellation

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

(9,867)

from $62

Boston Harbor Sightseeing Cruise

(469)

from $71

Sightseeing Day Sail around Boston Harbor

(252)

from $46

1 hour 30 minutes to 2 hoursFree Cancellation

4.8

(607)

from $54

Boston Harbor Narrated Sunset Cruise

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.

4.2

(567)

from $29

City Cruises Boston Premier Dinner Cruise on Odyssey

City Cruises Boston Premier Dinner Cruise on Odyssey

2 to 3 hoursFree Cancellation

3.7

(190)

from $133

City Cruises Boston Signature Lunch Cruise

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.

4.3

(143)

from $79

Boston Harbor Cruise Aboard Yacht Patriot

Boston Harbor Cruise Aboard Yacht Patriot

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.

4.7

(11)

from $51

Boston Summer Nights Trolley Tour plus River Cruise

Boston Summer Nights Trolley Tour plus River Cruise

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.

(174)

from $49

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

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.

4.3

(5,857)

from $51

Boston Harbor Brunch Cruise

What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery + Cafe. Feel free to bring your own food along if you prefer, but please no outside beverages and no coolers. Mimosas are $5 all morning! We also have our full drink menu available including local craft beers, cocktails, wine, soda, juice, and water. We accept Apple Pay, credit cards, or cash onboard.

(160)

from $106

Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

New England Fall Lunch Cruise in Boston Harbor

5.0

(20)

from $73

City Cruises Boston: Signature Dinner Cruise

4.4

(44)

from $82

2 to 3 hoursFree Cancellation

4.0

(313)

from $114

Likely to Sell Out

City Cruises Boston Codzilla High-Speed Thrill Boat Ride

45 minutesFree Cancellation

4.2

(434)

from $56

City Cruises Boston Premier Brunch Cruise on Odyssey

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

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.

(30)

from $104

Boston to Kennebunkport with Optional Lobster Tour

Boston to Kennebunkport with Optional Lobster Tour

8 to 10 hoursFree Cancellation

4.8

(46)

from $125

Celebrate a special occasion or just enjoy the company of your family and friends on this leaf-peeping Boston Harbor brunch cruise. On board a 1920s-style yacht, the Northern Lights, you’ll sail through Boston Harbor, cruise past the Harbor Islands, and spot landmarks and beautiful fall scenery along the way. Indulge in a fresh, gourmet brunch prepared by the onboard chef as you take in the waterfront views.

Boston Harbor Fall Brunch Cruise

Boston Harbor Sunset Sail Tour

4.4

(23)

from $106

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Top Attractions in Boston

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Attractions

What are people saying about Boston

ERICK_C, Jun 2026

Wonderful Sunset Cruise

We had such a nice time. The sunset over the Boston skyline was beautiful and the staff and ship are very nice. Captain Dante was great as well as the staff, Charlie and others were excellent at pointing out landmarks, explaining the ship workings and generally giving pointers on visiting the city. It was a great time!

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!

Lexington and Concord 3 hour private car tour from Boston

Clinton_E, Mar 2026

A highly recommended, brilliant tour!

We absolutely loved our tour of Lexington and Concord with Martin, the best tour guide in New England! He picked us up from our hotel right on time in a clean, new minivan. He gave us a brief photo review of the land-filling that created the Back Bay (as our hotel was there). He then gave us a drive-through bonus tour of a bit of MIT and Harvard on the way to Lexington. We were able to briefly walk the long corridor of MIT and see the unbelievable freshman dining hall at Harvard. Both on the road and when out of the van in Lexington and Corcord, Martin demonstrated a captivating style of history telling that really intrigued the listener. He is clearly passionate about the details of the events of April 19, 1775. I was easily able to visualize the incredible drama that unfolded in these towns on that day. Because of this, standing on Lexington green was very moving for me. Near the end of our tour, he gave us a bonus drive-by of Bunker Hill and provided us with some additional history. He then walked us in to the Warren Tavern, so to insure that we found a great seat. This was my fifth or sixth trip to Boston, and can say without hesitation that this or any of Martin’s company’s tours will stand above the rest (we also took the full-day private tour of Salem and the coast with Martin)!

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!

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.

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!

Private Boston, Lexington & Concord Historical Tour

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!

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!

Highlights of Boston Private Tour

Lisa_Y, Sep 2025

It was a private tour and...

It was a private tour and Marybeth was excellent and met on all our requests above and beyond. We went passed Harvard university and MIT…heard many stories about the campus and the Great Dom Hack about Harvard’s plank. We drove by Italian town and Chinatown. Ate at the famous Cheers and was delicious. We had a non walking tour as requested…mainly drove around town.

Boston Private City Tour

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!