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Liberty Fleet of Tall Ships

Boston Harbor Sailing & Bahamas Windjammer Cruises

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Tall Ship Transit Cruises & Races

Join us for a tall ship sailing cruise along the Atlantic!

Bahamas Windjammer Sailboat Cruise

Weekly trips available December 2020 – May 2021

Join us on the water today and experience Boston’s favorite tall ships!

Come aboard with Liberty Fleet of Tall Ships for an unforgettable tall ship sailing excursion in Boston during the summer, or join us during the winter on a windjammer cruise for a relaxing barefoot-style cruise in The Bahamas!

We offer tall ship day sails and charters, which are the best way to experience Boston’s historic harbor and enjoy unparalleled views of the city with coworkers, friends, and family!

The Tall Ship Liberty Star
Liberty Clipper on Deck
Morning Sail on a Tall Ship
Group photo on the liberty fleet's ship
team building charter
Liberty Fleet corporate outings
Private events on Liberty Fleet's vessels

Five-Star Reviews from TripAdvisor

Cruising the Bahamas...

No kidding, this is one of the BEST vacations, and most uniques experiences WE HAVE EVER HAD. Don’t miss the chance to do it. There were passengers from late thirties to mid-seventies aboard, and everyone enjoyed themselves.

– Bob L., TripAdvisor
Satisfying Sailing Experience

The snorkeling was excellent including coral rocks and islands, and even a sunken freighter. One of the best traveling experiences we have every had. Would not hesitate to recommend to anyone looking for an exciting and satisfying sailing experience.

– Jim, TripAdvisor
Fantastic Experience

Sailing on a tall ship is like no other vacation. If you’ve ever wanted to do it, it doesn’t get any better than the Liberty Clipper. The crew, Captain Noah, Andrew, Ben, Rikka, Mitch, Jewel, Cam, Brian and Lincoln were excellent!

– 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