Liberty Fleet of Tall Ships

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Bahamas Windjammer Vacations & Boston Harbor Sailing

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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!

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.

5-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.

Satisfying Sailing Experience

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

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.