Gloucester Schooner Race (Labor Day Weekend)

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

Saturday (Travel Day)
$125
Sunday (Race Day)
$160
Monday (Travel Day)
$125

The famous Gloucester Schooner Race! Book now to sail from Boston to Gloucester or back, and even book a spot on the boat for race day! You won't forget this exhilarating experience!

New England Labor Day Weekend Windjammer Cruise – Sail a leg of the Gloucester Race!


Boston Sail to 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.
  • 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 offshore and racing in Gloucester, MA! Join us for the fun and true offshore sailing experience…

Activity Schedule for 2018

Schedule of Events for Saturday, September 1

  • Boarding: 8 a.m.: Boarding begins for our offshore adventure. Enjoy coffee and breakfast on deck as we prepare the ship to get underway. If you are coming in from out of town, you may stay on board the night before – call us for details!
  • Offshore sailing!! 9 a.m. – 4 p.m.: The ship sails offshore 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!

Schedule of Events for Sunday, September 2

  • 8 – 8:30 a.m.: Boarding for day cruise passengers. 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!

Schedule of Events for Monday, September 3

  • 8 a.m.: Begin boarding for day cruise passengers.
  • 9 a.m. – 4 p.m.: The ship sails offshore 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. We’ll have a special lunch prepared courtesy of our Professional Chef!