Top Boston Sunset Cruises

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

4.6

(705)

from $54

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

4.6

(448)

from $71

Boston Harbor Sunset Sail Tour

4.8

(158)

from $82

Boston Harbor Narrated Sunset Cruise

1 hour 30 minutesFree Cancellation

4.2

(560)

from $29

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

4.7

(718)

from $40

City Cruises Boston: Signature Dinner Cruise

2 to 3 hoursFree Cancellation

4.0

(308)

from $114

City Cruises Boston Historic Sightseeing Harbor Cruise

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

(1,459)

from $46

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

City Cruises Boston Whale Watching Cruise by High-Speed Boat

3 hours 30 minutesFree Cancellation

4.5

(3,250)

from $86

City Cruises Boston Signature Lunch 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.

4.3

(140)

from $79

City Cruises Boston Premier Dinner Cruise on Odyssey

City Cruises Boston Premier Dinner Cruise on Odyssey

2 to 3 hoursFree Cancellation

3.7

(186)

from $133

Boston Harbor Sightseeing Cruise

1 hour 30 minutesFree Cancellation

4.5

(242)

from $46

Sightseeing Day Sail around Boston Harbor

1 hour 30 minutes to 2 hoursFree Cancellation

4.8

(586)

from $67

City Cruises Boston Codzilla High-Speed Thrill Boat Ride

45 minutesFree Cancellation

4.2

(428)

from $56

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

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

Boston Ghosts and Gravestones Trolley Tour

4.3

(5,794)

from $51

4.4

(2,546)

from $46

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

Boston Tea Party Ships and Museum Admission

1 hourFree Cancellation

4.7

(2,759)

from $36

Boston Harbor Private Sunset & Foliage Cruise, on Yacht Trinacria

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

from $1,200

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

1 hour 45 minutesFree Cancellation

4.6

(2,675)

from $26

Top Attractions in Boston

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Attractions

What are people saying about Boston

Boston Harbor Sunset Sail Tour

Marjorie_T, Jul 2026

Amazing experience.

What an amazing experience! Everything was perfect from our purchase to sailing on the Adirondak III. The weather and views were perfect and the crew was amazing. Charlie and Hannah worked hard to get the sails up and then they walk around waiting on you (drinks and cocktails) on the moving vessel so easily. It was an ex Cc ellent trip and we got a lot of nice pictures.

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Josephine_H, Jul 2026

A Must-Do in Boston!

We had a beautiful evening on the sunset cruise. Captain Jack and his crew were wonderful. The tall ship is gorgeous, and there is a decent selection of drinks. The tour isn't narrated, but the crew were happy to help guests with any questions they had. Everyone visiting Boston should experience it from the water, and there's no better way to do it!

Classic Tall Ship Cruise in Boston Harbor

Sharee_P, Jul 2026

Excellent afternoon!

Absolutely wonderful way to spend an hour and a half during a trip to Boston! All three crew were extremely helpful and friendly. It was so relaxing to be out on the water and to get to see the city from a different viewpoint. My only wish was that we could have stayed out for another couple hours, but I guess that means we will come back again sometime!

Boston Harbor Sightseeing Cruise

Tricia_W, Jul 2026

Great ride, even for locals

It was a perfect boat ride, with just enough info about landmarks shared along the way! We aren’t tourists (we live in Boston area) so we wanted to enjoy the ride without lots of interruptions and this ride was perfect! Also appreciated the bar for drinks and snacks…and I felt the prices were fair. Overall a really nice time!

Sightseeing Day Sail around Boston Harbor

crystal_r, Jun 2026

Very cool experience

First of all I have never been on a sail boat before it was incredible to watch the crew manage the sails and keep us moving along at quite a clip. Also almost as impressive was how they managed to keep us all topped up on drinks at the same time. It was a very cool experience and I'm very glad I did it. Well worth it and I would definitely recommend if your looking for something a little different to do while your in the city.

City Cruises Boston Historic Sightseeing Harbor Cruise

Claire_M, May 2026

Awesome tourist attraction!!

I had David as our tour narrator and he was amazing!! As a solo traveller I was skeptical on doing this alone but as soon as I got on the boat it was super easy and super fun! Dave is hilarious and has a great sense of humour! Didn’t think this was really my thing but LOVED it and so glad I went!! I learned so much!

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 90-Minute Harbor Sunset Sightseeing Cruise

Amanda_T, Sep 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.