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Liberty Fleet of Tall Ships

Boston Harbor Sailing Cruises

Featured Boston Sailing Experiences

Read what guests are saying about their sailing experience with Liberty Fleet in Boston!

Read what guests are saying about their sailing experience with Liberty Fleet in Boston!

Outstanding and friendly staff - fun event to start off a Saturday. Great views around Boston Harbor and sailing experience.

Mike M. | Tripadvisor

The cruise and crew were amazing. The scenery was beautiful. Awesome pastries from Flour bakery. I’ve did the sunset cruise years ago and I would do them both again.

Meander | Tripadvisor

This was such a beautiful memory for my daughter and I. We sat and drank our mimosas and the peaceful beauty with everything just made the trip! The crew is sooo nice!! The brunch desserts are perfect! The flour bakery is outstanding. Overall.. moments that will last a long time. Recommend highly!!!!

Amy G. | Tripadvisor

Fantastic! Friendly crew. The mimosas were delicious and the treats were wonderful! A great range of them! The sailing was beautiful and they offered to take pics for us.

Stunning Views and Relaxing Pace

The view of the harbor was amazing and the experience of the tall ship was one of a kind. The crew was friendly, knowledgeable, and always available to help. We also loved the relaxing pace of the sail.

– Lydia T., Tripadvisor
Wonderful Ride

It was just wonderful. My husband got to help raise the two large sails. I really enjoyed that we actually sailed around the harbor. The engine was only used for leaving and returning to the wharf. The crew was awesome.

– Eira M., Tripadvisor
Bachelorette Party

We danced with strangers, sang, laughed and had a wonderful time! I don't plan on having another bachelorette party, but if I do, I'd do this again! 6/5 stars!

– Stephanie P., Tripadvisor
Loved It!

We loved seeing Boston this way. The sunset was beautiful and the crew was friendly. My only regret is that we didn’t do the longer cruise.

– Melodee W., Tripadvisor