Sightseeing Cruises

Boston Sightseeing Cruises

4.8/5(105)

Sherman H

Couple

Verified booking

3 weeks ago

The tour giude/narrator was knowledgeable, comical and engaging. he made the tour so much more than what I expected. The tour guide gave us historical information, taught me the difference in a pier and wharf and even provided information about yachts, naval ships in the harbor. It was a wonderful cruise, I would recommend to anyone visiting Boston.

Ashley B

Family

Verified booking

Last week

Such a fun activity. I live in Boston, but decided to be a tourist in my own city. Took my 2 year old son to enjoy the water and I learned some history about Boston! 10/10 would do again.

Dorianne D

Couple

Verified booking

Sep 2026

Appreciated the sunset sail! It was a very relaxing excursion. The vessel was very clean and the crew were friendly, helpful and knowledgeable. Highly recommend this experience

Lynne M

Group

Verified booking

2 weeks ago

Seeing Boston from the water very different perspective I learned some historical facts I was not aware of As a Boston native it was a new adventure for me

David S

Couple

Verified booking

Aug 2026

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!

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.

105 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
Ashley B
Family
Verified booking
Last week
Such a fun activity. I live in Boston, but decided to be a tourist in my own city. Took my 2 year old son to enjoy the water and I learned some history about Boston! 10/10 would do again.
Sherman H
Couple
Verified booking
3 weeks ago
The tour giude/narrator was knowledgeable, comical and engaging. he made the tour so much more than what I expected. The tour guide gave us historical information, taught me the difference in a pier and wharf and even provided information about yachts, naval ships in the harbor. It was a wonderful cruise, I would recommend to anyone visiting Boston.
Dorianne D
Couple
Verified booking
Sep 2026
Appreciated the sunset sail! It was a very relaxing excursion. The vessel was very clean and the crew were friendly, helpful and knowledgeable. Highly recommend this experience
Lynne M
Group
Verified booking
2 weeks ago
Seeing Boston from the water very different perspective I learned some historical facts I was not aware of As a Boston native it was a new adventure for me
Kevin E
Couple
Verified booking
2 weeks ago
Two of us took the sunset cruise. Great view of the harbour and sunset. The narrative was enjoyable. It was a great evening.

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.