Skip to primary navigation Skip to content Skip to footer

Liberty Fleet of Tall Ships

Boston Harbor Sailing & Bahamas Windjammer Cruises

Download Boston or Bahamas? Choose your cruise here!

Open for the 2022 Season! Clean & Safe

Thank you for Supporting Small Business!
Liberty Fleet of Tall Ships will follow the guidelines set by the Bahamas as we strive to keep crew and passengers healthy.

 

Based on the current guidelines which have been put in place by the Bahamas (where we sail exclusively in the winter season, no other countries), Liberty Fleet of Tall Ships will have to require passengers to be vaccinated in order to comply with the country’s guidelines.  You can check https://travel.gov.bs for the most up-to-date requirements for the Bahamas Travel Health Visa and please keep in mind that these restrictions and guidelines may be subject to change.
Clean and Safe Logo

Bahamas Windjammer Cruise

From $1499

Liberty Fleet is looking forward to returning to the beautiful Bahamas for the 2022/2023 Winter season!  Set sail for new horizons on a barefoot cruise exploring the many islands and pristine beaches! Your perfect vacation is our top priority, and we strive to maximize your safety and enjoyment.

Learn More
  • Winter
  • 7 Days

Browse Boston Excursions!

Boston Harbor Sailing Cruises

Returning in Spring 2023!

Tall Ship Transit Cruises & Races

Join us for a tall ship sailing cruise along the Atlantic
  • Fan Favorite Cruise!

Boston Sunset Harbor Cruise on a Tall Ship

From $49

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!

Learn More
  • Summer, Fall
  • 1.5-2 Hours

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 day sails and charters, which are the best way to experience Boston’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 day sails, sunset sails, and our specialty Sunday Brunch 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