New England Sailing Destinations

A New England tall ship cruise aboard the majestic LIBERTY CLIPPER offers you the opportunity to explore the beautiful coast of New England by sea. Come join us for a memorable sailing vacation cruise in a world renowned sailing destination and discover all that coastal New England has to offer. The Liberty Clipper's home port is historic Boston Harbor. From here you can join her for the annual Gloucester Schooner Race in Gloucester, Massachusetts every Labor Day Weekend, or sail with her in October as she makes her way south along the Atlantic coast with stops in New York, Baltimore, and Virginia. Along the way she's likely to sail along and even stop at some of New England's iconic islands such as Nantucket and Martha's Vineyard. From offshore schooner races to island cruises and coastal voyages, we've got a sailing cruise for everyone!

Experience the excitement of a tall ship schooner race!

Gloucester Schooner Race

Set sail on the Liberty Clipper for the Gloucester Schooner Race! Each Labor Day weekend dozens of schooners sail off Cape Ann, Massachusetts during this annual gathering of tall ships. Come aboard for the full 3-day round trip excursion from Boston, or join us in the historic seaport town of Gloucester the day of the race!


Sail with the Liberty Clipper from Boston To New York

Boston to New York City
Islands of New England Sailing Cruise

The LIBERTY CLIPPER will follow the coast southwards along New England stopping at various islands and small coastal towns. We may visit Nantucket, Martha's Vineyard, Cuttyhunk, Block Island, Long Island, or any other combination of coastal ports on the way to NYC.


Enjoy beautiful sunrises and sunsets offshore on a New York to Baltimore sailing cruise!

New York City to Baltimore
Mid-Atlantic Offshore Sailing Cruise

This cruise mixes the best elements of our more relaxed "windjammer-style" cruises with an offshore element to bring you a vacation cruise that you will never forget. We will enjoy some wonderful sunrises and sunsets at sea and possibly even see whales and dolphins along the way. We try to catch at least one of our meals on the way and always have a blast on this trip into the Atlantic!