- Special Event Season Special Event
- 3 Days Duration 3 Days
Join us for the whole three-day round-trip excursion from Boston on our New England Labor Day Weekend windjammer cruise!
Boston Sailing Returning in 2023!
Boston → Gloucester → Boston
Quick Details
Sail to Gloucester from Boston for the Schooner Race
Set sail on the Liberty Clipper for the Gloucester Schooner Race! Come aboard the Liberty Clipper and sail from Boston to Gloucester for the whole weekend, or for just the ride up, and take a ride on a participating tall ship on Race Day! You won’t forget this exhilarating experience!
Each Labor Day weekend, dozens of schooners sail off Cape Ann, Massachusetts, during this annual gathering of tall ships. This weekend of special sailing events is an annual favorite and space is limited, so book today!
We won’t be in Boston this weekend — we’ll be sailing along the coast and racing in Gloucester, MA! Join us for the fun and historic sailing experience!
Three-Day Gloucester Schooner Race Cruise Starts on Saturday
Depart Boston on Saturday and be aboard the Schooner Liberty Clipper for the entire Northbound Transit, Race day in Gloucester on Sunday, and Southbound Transit back to Boston on Monday. All meals are provided, and guests attend the award ceremony following the race with captain and crew.
Northbound Sail Up to Gloucester Starts on Saturday
Up to 12 additional guests come aboard for the sail up to Gloucester and depart once we arrive. Breakfast and lunch are provided on board as we sail north up Cape Ann. Northbound guests depart once we get to Gloucester. This is a one-way trip.
Race Day in Gloucester on Sunday
Up to 12 additional guests come aboard as The Liberty Clipper participates in the annual Gloucester Schooner Race and depart at the end of the race. Breakfast and lunch are provided on board as we sail.
Southbound Sail from Gloucester to Boston on Monday
Up to 12 additional guests come aboard for the sail back to Boston and depart once we arrive. Breakfast and lunch are provided on board as we sail south. This is a one-way trip.
Join us for the whole three-day round-trip excursion from Boston on our New England Labor Day Weekend windjammer cruise!
Come aboard for a day sail in Boston Harbor on one of our classic schooners! Sailing is a great, family-friendly way to see Boston from a new viewpoint.
Come sail with us on Boston Harbor for a delicious brunch under a canopy of sails.