Liberty Fleet of Tall Ships

Boston Harbor Sailing Cruises

Liberty Fleet is excited to be back in Boston for 2019!

Check out our Tall Ship Cruises

Day Sailing

1.5 - 2 Hours

Enjoy a Boston Sail Aboard One of Our Classic Schooners!

Day Sailing

Enjoy a Boston Sail Aboard One of Our Classic Schooners!

Sunset Cruises

1.5 - 2 Hours

Experience a Boston Sunset Sail on a Tall Ship!

Sunset Cruises

Experience a Boston Sunset Sail on a Tall Ship!

Sunday Brunch Sail

Starting at $55 | 2.5 Hours | Liberty Clipper

Come sail with us on Boston Harbor for a delicious brunch under a canopy of sails.

Sunday Brunch Sail

Come sail with us on Boston Harbor for a delicious brunch under a canopy of sails.

Rum & Revelry Sail

Ages 21+ | Saturdays | Liberty Clipper

A Rum Tasting at Sea (okay, the harbor, but it's almost like the sea!)

Rum & Revelry Sail

A Rum Tasting at Sea (okay, the harbor, but it's almost like the sea!)

Search By Date

5-Star Reviews from 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.

Fantastic Gift

My husband and I were gifted a harbor cruise by our daughter and it was fabulous! It was a beautiful day on the water and the crew was so much fun! A must do if you are in Boston! Thank you to the crew! – Terry S.

Boston “To Do”

The crew was very professional. They were very polite. It was as advertised, sail around the Boston harbor at sunset. The sun setting behind the skyline is awesome! I would have to say that I would definitely encourage anyone visiting Boston to add this to their “TO DO” list. – Ernest C.

About Liberty Fleet

The Liberty Fleet is Boston’s only fleet of tall ships; we have been sailing Boston Harbor since 1993 and would love to bring you on board one of our classic schooners! While sailing Boston on a tall ship harbor cruise, you’ll be welcome to help hoist the sails, take the helm, enjoy a drink or snack from the ship’s bar, or just relax and take in the sights and sounds of Boston Harbor.  We sail with the best wind for the day, and may find ourselves visiting Charlestown and the historic North End, or sailing out to view Fort Independence and the spectacular Boston Harbor Islands.