Liberty Fleet of Tall Ships
Boston Harbor Sailing & Bahamas Windjammer Cruises
Come aboard the Liberty Clipper for an unforgettable tall ship sailing excursion in Boston, or join us on the Windjammer for a relaxing charter! Take in the amazing sights of Boston Harbor, enjoy the wind in your hair and in the sails, and maybe even take the helm. Our tall ship charters are the best way to experience the city’s waterways and enjoy unparalleled views of the city. Join us on the water today!
Select My Excursion
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!
Upcoming Transits
Boston to New York City
This trip mixes the best of our laid back barefoot style cruises with a little adventure of near coastal sailing!
New York City to Baltimore
This trip is perfect if you’re looking to earn your sea-legs, get some navigation or sailing experience, or are curious about what life “offshore” is all aboard.
5-Star Reviews from TripAdvisor
Liberty Fleet of Tall Ships
