Sightseeing Cruises

Boston Sightseeing Cruises

4.8/5(74)

David S

Couple

Verified booking

3 weeks ago

The Boston Harbor sunset cruise was one of my favorite parts of our time in the city. The views of the Boston skyline from the water were beautiful, especially as the sun started to go down and the city lights came on. The atmosphere was relaxed and made it easy to just enjoy the ride, take pictures, and spend time together. The crew was friendly, everything felt well organized, and the cruise was a really nice change of pace from walking around the city. I’d definitely recommend it for couples, visitors, or even locals looking for a fun and relaxing evening in Boston. I would absolutely do it again.

Cynthia W

Group

Verified booking

Jul 2026

We really enjoyed the Boston Historic cruise! We sat on the top of the boat close to the presenter. He was fabulous! We learned so much about the Boston Harbor and surrounding waters. We got to see several important monuments, locations, and ships of our country's/Boston's vast history. Our narrator/tour guide, Kevin, was incredibly informative and the way he presented the information was fun and almost like we were in a story! We got to see the Bunker Hill monument, the USS Constitution, and more!

Matthew H

Couple

Verified booking

Jul 2026

We did the Boston Harbor sunset cruise on Friday July 24th. It was a beautiful and informative time. We watched planes from the Boston airport land and take off. We saw the end of day ceremony at the USS Constitution. They offered food and drinks for purchase. The entry and exit process was smooth and there were plenty of seating options. We really enjoyed the cruise!

Aileen I

Group

Verified booking

Jul 2026

The cruise was a lovely experience despite the rainy weather. It was great historical experience with a unique vantage point, different from the many other Boston historical experiences. The narrator Emily was great. Al the staff was very helpful and experienced.

Marilyn A

Group

Verified booking

Jul 2026

Adam was great and very informative. We learned lots of history about the coastline of Boston. The only negative was that there was a small group of guests that were inconsiderate of others- were loud, and thought they were on a party cruise

Sail through Boston Harbor while listening to stories about the city’s Revolutionary War history, maritime legends, and famous waterfront landmarks.

Enjoy panoramic views of Boston’s skyline, harbor islands, and historic sites from spacious outdoor decks or comfortable indoor seating areas.

Learn from professional onboard guides who bring Boston Harbor’s past and present to life through engaging live narration.

Watch the harbor transform during sunset on the upgraded evening cruise, offering a more atmospheric experience across the waterfront.

Choose the Historic Boston Harbor Cruise for a shorter daytime sightseeing experience or upgrade to the Narrated Historic Sunset Cruise for evening skyline views.

Boston Harbor sightseeing cruise (as per option selected)

Boston Harbor sunset sightseeing cruise (as per option selected)

Professional narrated commentary by onboard guides

Scenic harbor and skyline views

Indoor seating with large windows

Outdoor observation deck access

Historic and maritime storytelling

Food and beverages

Alcoholic drinks

Hotel transportation

Optional gratuities

TOTAL DURATION1 hour - 0 minutes
FREQUENCY5
MODE OF TRANSFERCruise Ship
Timeline
Map
Sights covered
Boston Harbor Islands
Boston Skyline
Historic Waterfront Sites
Revolutionary War Landmarks
Boston Harbor
USS Constitution (“Old Ironsides”)
Bunker Hill Monument
Boston Navy Yard / Charlestown Navy Yard
Fort Independence & Castle Island
Logan International Airport Waterfront

These tickets can't be cancelled or rescheduled.

74 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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What our guests say
David S
Couple
Verified booking
3 weeks ago
The Boston Harbor sunset cruise was one of my favorite parts of our time in the city. The views of the Boston skyline from the water were beautiful, especially as the sun started to go down and the city lights came on. The atmosphere was relaxed and made it easy to just enjoy the ride, take pictures, and spend time together. The crew was friendly, everything felt well organized, and the cruise was a really nice change of pace from walking around the city. I’d definitely recommend it for couples, visitors, or even locals looking for a fun and relaxing evening in Boston. I would absolutely do it again.
Sandra B
Group
Verified booking
2 weeks ago
The cruise was very pleasant and the best part was our knowledgeable tour guide. The tour guide was excellent he was informative and polite.
Judit C
Couple
Verified booking
2 weeks ago
Tge guide was fenomenal! Sorry, I dont remember her name, she was amazing and made the experience so much better! Thank you!
Martha B
Family
Verified booking
Aug 2026
Great looking for my refund for these tickets. This part of my party couldn't make it because their flight was cancelled.
Wendy H
Couple
Verified booking
3 weeks ago
Learning about the history of Boston was extremely enlightening! So much I didn't know! The view was amazing!

What to bring

Mobile or printed ticket confirmation

Light jacket for cooler harbor breezes

Camera or phone for photos

What’s not allowed

Large luggage or oversized bags

Outside alcoholic beverages

Smoking inside enclosed areas

Accessibility

Indoor seating areas are accessible for most guests

Restrooms are available on board

Boarding assistance may be available upon request

Additional informationThe

Historic Boston Harbor Cruise duration is approximately 1 hour

Narrated Historic Sunset Cruise duration is approximately 1.5 hours

Cruises depart from Long Wharf in Boston

Guests should arrive at least 15 minutes before departure

Tickets are non-refundable

Schedules and cruise times may vary depending on operational conditions

Snacks and beverages are available for purchase on board

Cash and major credit cards are accepted onboard

Your voucher will be emailed to you shortly.

Display the voucher on your mobile phone with a valid photo ID at the starting point.

Please check your final voucher for the starting point details & specific instructions.