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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!

  • LIBERTY FLEET IS GETTING READY FOR SUMMER 2021!
  • CALENDAR TO BE PUBLISHED IN SPRING 2021 - please check back.
From $43
  • 1.5-2 Hours
  • Summer

Boston Harbor Sailing Cruises

Come aboard for a day sail in Boston on one of our classic schooners! Sailing is a great, family-friendly way to see Boston from a new viewpoint.

Anchor 2021 DATES TO BE POSTED SOON! Please check back
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  • Learn about Boston's History from a Unique Perspective.
  • Returning in 2021.
From $45
  • 2 Hours
  • Summer

Harbor History Sailing Cruise on a Tall Ship

“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…

Anchor 2021 DATES TO BE POSTED SOON! Please check back.
Learn More