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Boston Harbor Sailing Cruises


Anchor Choose Your Cruise

Check Out Our Tall Ship Cruises!

Our Boston cruises are operating at 50% capacity for your safety and pleasure!
  • Learn about Boston's History from a unique perspective.
  • Returning in 2021.
From $38

“A SAIL THROUGH TIME”  Learn about Boston’s history while aboard a classic schooner. The cruise follows the paths of ships like the Flying Cloud, Astrea, and Columbia, exploring how their voyages shaped Boston and helped…

About Liberty Fleet

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’re be welcome to help hoist the sails, take the helm, enjoy a drink 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.