Top Boston Sunset Cruises

Boston Harbor Sunset Cruise

4.6

(658)

Boston Harbor Sunset Sail Tour

from $54

Likely to Sell Out

4.8

(134)

Boston Harbor Narrated Sunset Cruise

from $82

4.2

(541)

1 hour 30 minutesFree Cancellation

from $29

4.4

(412)

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

1 hour 30 minutesFree Cancellation

from $56

4.6

(414)

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Boston Harbor Sightseeing Cruise

from $81

Special Offer

4.5

(203)

1 hour 30 minutesFree Cancellation

from

$41

$46

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

4.5

(1,404)

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

(166)

2 to 3 hoursFree Cancellation

from $133

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

4.4

(3,116)

3 hours 30 minutesFree Cancellation

from $86

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

Special Offer

4.8

(544)

Sightseeing Day Sail around Boston Harbor

1 hour 30 minutes to 2 hoursFree Cancellation

City Cruises Boston: Signature Dinner Cruise

2 to 3 hoursFree Cancellation

from $114

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

(2,597)

1 hourFree Cancellation

from $36

Witness the breathtaking Boston Harbor skyline and many landmarks from the unique perspective of the harbor. We are one of the only Private Sunset Cruises in Boston. The Boat will only have you, your guests and our crew. We will provide complimentary Water and Soft Drinks. You are welcome bring you favorite food and Beverages on-board to enjoy during your cruise. As a reminder Gratuities are not included in your fare. This Tour runs over a 10 to 12 mile loop of the harbor which takes 2 Hours and 30 Minutes. You will have plenty of time to take photos and make lasting memories. we travel at a slow rate of speed and the cruise is very enjoyable. AS THE DAYS GET SHORTER Start and end times will be modified in order to coincide with sunset times. TRIP MAY BECOME LESS THAN 2.5 HOURS Trip ends 30 minutes after sunset in Aug/Sept.

Boston Harbor Private Sunset & Foliage Cruise, on Yacht Trinacria

5.0

(1)

2 hours

from $1,200

Per group

Walk the Freedom Trail with a guide in historic costume on a tour from Boston Common to Faneuil Hall, a 1.2-mile route that covers important sites in the heart of Boston. This tour's shorter distance lets you follow in the footsteps of the founding fathers and American revolutionaries without making the more strenuous trek all the way across the Charles River, finishing in a spot that’s convenient to top Boston attractions.

Boston Freedom Trail Walking Tour with Costumed Guide

4.6

(2,579)

1 hour 45 minutesFree Cancellation

from $26

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

4.3

(5,654)

Boston Ghosts and Gravestones Trolley Tour

from $52

4.4

(2,469)

City Cruises Boston Codzilla High-Speed Thrill Boat Ride

from $47

4.2

(424)

45 minutesFree Cancellation

from $56

Likely to Sell Out

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)

Boston Harbor Sunset Sail Tour

from $104

Top Attractions in Boston

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Attractions

What are people saying about Boston

Amanda_S, May 2026

Excellent cruise with great city views!

Our sunset cruise was amazing! Great views of the city skyline and the surrounding area. The crew, Alex, Claire, Charlie and Eric were so friendly and shared so much knowledge about the city. We would highly recommend this cruise and hope to go on another when we return to Boston.

Boston Harbor Sunset Cruise

Olivia_F, Apr 2026

Perfect evening activity!

Perfect evening activity! Although it was cold, it was still a great way to see the city. The boat had a great cocktail and alcohol options. The staff was friendly and the captain was knowledgeable of viewpoints along the way. We even got to see the USS Constitution fire off a canon at sunset! Highly recommend if you love boats and a scenic view!

City Cruises Boston Whale Watching Cruise by High-Speed Boat

Cordula_C, Oct 2025

Loved it !

This was well worth it. Would do it again. Once we were in “whale-territory” they took their time letting us observe the whales, while explaining what the whales were doing and then searching for and finding more whales to appear. On the way back we had the opportunity to ask more questions.

City Cruises Boston Historic Sightseeing Harbor Cruise

Julie_K, Oct 2025

Great View's from the Ship

A good way to see the city from the ship. Was happy to see the US Constitution and get a good photo. It is fascinating to watch the planes fly overhead. It show the contrast from old Boston and new Boston. The top deck has the best views. Book it early because it fills up fast.

Sightseeing Day Sail around Boston Harbor

Brad_Y, Oct 2025

Great day with coworkers on the water

We had a great day! It was an impromptu team bonding opportunity, and the weather was perfect to be on the water. The crew was kind and informative, but let us have our own space and conversations, but there when you wanted them. The captain had been sailing this ship for 10 years and was a true pro. Unlike lots of sailboat excursions, the captain cut the motors and ran by sail for almost the entire trip. Loved it!

Classic Tall Ship Cruise in Boston Harbor

krislynn5477, Sept 2025

Sailing with Captain...

Sailing with Captain Fredo and his crew on Boston Harbor was an excellent experience. The boat was clean, well-maintained, and comfortable. Captain Fredo demonstrated great knowledge of the harbor and navigated confidently, which made the trip smooth and enjoyable. The crew was attentive and professional, ensuring that everything ran efficiently without being intrusive. The views of the Boston skyline from the water provided a unique perspective of the city, making it a memorable outing. I would recommend this cruise to anyone looking for a relaxed and well-organized sail in Boston Harbor.

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

Amanda_T, Sept 2025

Don't Be Late

They are not kidding when they say late arrivals will miss the boat. Boston traffic was crazy and we arrived 5 minutes just in time to wave goodbye to our friends on board leaving port. Our friends on board enjoyed the cruise but said it was crowded and there was not enough inside seating. Moral of the story arrive early and plan for Boston traffic.