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About Us

In 2024 the Liberty Fleet was purchased by Troy and Monica Sullivan and the Liberty Star became the flagship. For a variety of reasons they chose not to purchase the Liberty Clipper, which was previously a part of the Fleet.

It has been Troy’s dream to own a sailing business ever since he began sailing tall ships in his early 20s. He and Monica met aboard a schooner in CT in 2005 and between them have sailed extensively in the Atlantic, Pacific, Great Lakes, and Caribbean. They look forward to engaging their three children in their passion for sailing!

The Liberty Fleet has been operating day sails in Boston Harbor for 30 years. 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.

a group of people posing for a photo