Don’t miss your chance to set sail on a piece of living history and support a worthy cause! Thanks to the generosity of Canvas + Pine Sailing Expeditions, we’re raffling off a two-hour private sailing charter for six during 2024 Windjammer Days week, June 25 to June 28, 2024. This once-in-a-lifetime opportunity is a curated private sail aboard the Pilot Cutter Hesper, newly owned by East Boothbay sailor Eben Wilson and currently being commissioned for the season at Bristol Marine in Boothbay Harbor.

Hesper is a wooden, 60-foot, gaff-rigged pilot cutter handcrafted in 2004 by renowned boatbuilder Luke Powell in Cornwall, England. This beautiful vessel has cruised seas far and wide, from the rugged UK coast to the Arctic expanses and as far south as the Azores.

The winner will be selected on World Ocean Day, June 8, 2024 and will work directly with the captain to schedule their cruise — a $400 value! Set against the picturesque backdrop of the windjammers, this exclusive experience promises an unforgettable journey aboard a vessel revered for its elegance and seafaring prowess.

Purchase tickets through June 8, 2024 at 2pm:

  • By clicking on the link below
  • In person at 72 Oak St. Boothbay Harbor, Thursday-Saturday, 10am-2pm
  • By phone at (207) 633.0820
  • By mailing a check to (checks must be received by June 8, 2024):
    Boothbay Region Historical Society P.O. Box 272 Boothbay Harbor, ME 04538


Tickets are $20 each or six for $100. All proceeds will benefit the Boothbay Region Historical Society’s 2024 annual fund.