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Boston Harbor Sailing

If you’re planning on sailing in Boston Harbor, be sure you’re booking with Liberty Fleet! Massachusetts’ favorite sailing ship operator, we’re sure to impress! Try one of our daytime Boston Harbor sailing tours, or try a sunset sail! Care to sample some rum on the high seas? Perhaps the Rum Tasting Harbor Sail is for you. Whatever you’re looking for on your seafaring adventure, Liberty Fleet is the way to go!

  • 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…