Liberty Fleet of Tall Ships

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Boston Harbor Sailing & Bahamas Windjammer Cruises

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Boston Harbor Tall Ship Sailing

In Season until Mid-October! • From $35 • 1.5 – 2.5 Hour Cruises

While sailing Boston on a tall ship harbor cruise, you’re 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.

Windjammer Cruises

Weekly trips from October- May • From $600

Step away from the stresses of daily life and join us on the seafaring adventure of a lifetime. Liberty Fleet offers seasonal cruise vacations in the Bahamas, as well as some great point-to-point journeys between Boston, New York, Baltimore, and Portsmouth—you can even sail aboard our tall ship during the Great Chesapeake Bay Schooner Race! Explore our cruise options, and book today!

5-Star Reviews from 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.

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.

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.