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Boston Harbor Sailing Cruises


Anchor Choose Your Cruise

Check Out Our Tall Ship Cruises!

Our Boston cruises follow the strict guidelines of the City of Boston for your safety and pleasure.

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 after-hours Cocktails, Rum, &. City Lights Harbor Sail is for you. Whatever you’re looking for on your seafaring adventure, Liberty Fleet is the way to go!

We offer two tall ships for our Boston sailing cruises– The Liberty Star and Liberty Clipper. The Liberty Star is our smaller vessel at 67 feet, which is perfect for smaller groups; And our Liberty Clipper which is our larger vessel at 125 feet, making it ideal for large group outings. You can read more about each of our tall ships on our fleet page.

  • Cruises Begin June 2023!
From $48

“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 industrialize the country.  Tourguide / Onboard Docent from Boston By Foot.

Don’t let the arrival of Fall keep you from sailing.
Check out Liberty Fleet’s Southbound Transit Cruises coming in September 2022.

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.