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Liberty Fleet of Tall Ships

Boston Harbor Sailing Cruises

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The 2023 Boston Sailing Season Has Begun!

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  • Fan Favorite Cruise!

Boston Harbor Sunset Cruise on a Tall Ship

From $50

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic schooner!

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  • Summer, Fall
  • 1.5-2 Hours

Featured Cruise

  • HARBOR HISTORY CRUISE ON A TALL SHIP!
  • Cruises Begin June 2023!
From $48
  • Summer, Fall
  • 2 Hours

"A Sail Through Time" with Boston By Foot

“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.

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Browse Boston Harbor Cruises!

Boston Harbor Sailing Cruises

Returning in Spring 2023!

Join us on the water today and experience Boston’s favorite tall ships!

Come aboard with Liberty Fleet of Tall Ships for an unforgettable authentic tall ship sailing excursion in Boston during the summer with Boston Harbor public sails or private charters, or join us during the winter on a windjammer cruise for a relaxing barefoot-style cruise in The Bahamas!

We offer tall ship Boston Harbor cruises and charters, which are the best way to experience Boston sailing in the city’s historic harbor and enjoy unparalleled views of the city with coworkers, friends, and family!

On board, guests have the opportunity to temporarily become part of the crew and step back in time for a taste of what it was like to sail the magnificent ships that were once a common sight in every port. Sailing opportunities include harbor cruises, sunset sails, our specialty Boston Harborfest Sails, USS Constitution Turnaround Sails, and Rum & Revelry sails.

The Tall Ship Liberty Star
Liberty Clipper on Deck
Morning Sail on a Tall Ship
Group photo on the liberty fleet's ship
team building charter
Liberty Fleet corporate outings
Private events on Liberty Fleet's vessels

Five-Star Reviews from TripAdvisor

Cruising the Bahamas...

No kidding, this is one of the BEST vacations, and most uniques experiences WE HAVE EVER HAD. Don’t miss the chance to do it. There were passengers from late thirties to mid-seventies aboard, and everyone enjoyed themselves.

– Bob L., TripAdvisor
Satisfying Sailing Experience

The snorkeling was excellent including coral rocks and islands, and even a sunken freighter. One of the best traveling experiences we have every had. Would not hesitate to recommend to anyone looking for an exciting and satisfying sailing experience.

– Jim, TripAdvisor
Fantastic Experience

Sailing on a tall ship is like no other vacation. If you’ve ever wanted to do it, it doesn’t get any better than the Liberty Clipper. The crew, Captain Noah, Andrew, Ben, Rikka, Mitch, Jewel, Cam, Brian and Lincoln were excellent!

– Stephanie P., TripAdvisor
Loved it!

We loved seeing Boston this way. The sunset was beautiful and the crew was friendly. My only regret is that we didn’t do the longer cruise.

– Melodee W., TripAdvisor