Gloucester Schooner Race (Labor Day Weekend)

Boston → Gloucester → Boston | Starting at $125 per leg

Full 3 Day Excursion
$699
Saturday (Travel Day)
$125
Sunday (Race Day)
$160
Monday (Travel Day)
$125

The famous annual 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!

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! 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

3-Day Gloucester Schooner Race Cruise Starts Saturday September 5th

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

Northbound sail up to Gloucester Saturday Starts Saturday September 5th

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 7th

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.