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Gloucester Schooner Race

Boston → Gloucester → Boston

Quick Details

Full 3 Day Excursion
$699
Saturday Northbound Leg
$125
Sunday Race Day
$160
Monday Sounthbound Leg
$125

New England Labor Day Weekend Windjammer Cruise!

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!

Cruise Options

Three-Day Gloucester Schooner Race Cruise Starts Saturday, September 5

Depart Boston on Saturday, September 5 at 8 a.m. and be aboard the Schooner Liberty Clipper for the entire Northbound Transit, Race day in Gloucester on September 6, and Southbound Transit back to Boston on Monday, September 7. All meals are provided, and guests attend the award ceremony following the race with captain and crew.

Northbound Sail Up to Gloucester Starts Saturday, September 5

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

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 Monday, September 7

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.