- 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!
Quick Details
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 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.
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- Boarding: 8 a.m.: Boarding begins for our adventure. Enjoy coffee and breakfast on deck as we prepare the ship to get underway!
- Sailing!! 9 a.m. – 4 p.m.: The ship sails from Boston to Gloucester, MA. The ship sails out of Boston Harbor and passes Boston Light while making passage to the beautiful Cape Ann. On this leg of the cruise, you may see whales in Massachusetts Bay and will likely sail in the company of other schooners on their way to Gloucester for the 34th annual Gloucester Schooner Race.
- Lighted Boat Parade & Fireworks Cruise: The Liberty Clipper sails in Gloucester from 7:30 p.m. till approximately 10 p.m. to watch a lighted Parade of Sail and watch the fireworks! This part of the trip is only available to guests staying the whole weekend aboard.
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- 8 – 8:30 a.m.: Boarding for race day cruise. We depart promptly at 8:45 a.m. to line up for the race!
- 9 a.m. – 4/5 p.m. (approx.): The Liberty Clipper competes in the 30th annual Mayor’s Cup racing in the coastal waters off of Cape Ann, against a large fleet of tall ships! Bring your camera – events like this present rare opportunities to get some great pictures of a fleet of tall ships pressing forward under sail!
- Race Day Guests Depart after race concludes
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- 8 a.m.: Begin boarding for southbound day cruise passengers.
- 9 a.m. – 4 p.m.: The ship sails from Gloucester, MA to Boston, MA. The ship sails out of Gloucester bound south for Boston. On this leg of the cruise, you may see whales in Massachusetts Bay and will likely sail in the company of other schooners on their way home from the 34th annual Gloucester Schooner Race. Hear the crew tell their stories of the race and crew parties ashore. Lunch will be provided aboard during this southbound sail.