Boothbay Region Historical Society

Raffle for Windjammer Days sailing charter

Tue, 05/07/2024 - 7:15am

    Thanks to the generosity of Canvas + Pine Sailing Expeditions, Boothbay Region Historical Society is raffling a 2-hour private sailing charter for 6 during 2024 Windjammer Days, between June 25 to June 28. 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 raffle gives sailing enthusiasts and history buffs alike the chance to win a 2-hour private sail for up to six guests in Boothbay Harbor during Windjammer Days. The winner will be selected on June 8, and will work directly with the captain to schedule their cruise within those dates. 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.

    "We’re thrilled to offer this fundraiser for a chance to sail aboard Hesper and support a worthy local cause," says Hesper’s captain, Tom Hollyday. "Before our summer season of multi-day expeditions out of Camden begins, we’re excited to participate in Windjammer Days for the first time. Preservation and appreciation of seafaring heritage mean a lot to those of us in the wooden boat world. We’re happy to support the Boothbay Region Historical Society’s good work through this fundraiser raffle."

    Purchase raffle tickets by World Ocean Day June 8 by 2 p.m. through Boothbay Region Historical Society in several ways: online at, in person at the society’s 72 Oak Street museum in Boothbay Harbor open Thursday - Saturday 10 a.m. - 2 p.m., by mail (72 Ok St.), or by phone at 207-633-0820. Tickets are $20 each or six for $100. Raffle drawing will be at 2 p.m.  Saturday, June 8 at 2 p.m. The winner will be connected directly with the captain to schedule their sail—a $400 value!

    “We’re grateful to Eben and Tom for raffling off a sailing charter – which not only promises an unforgettable adventure, but also helps us share our coastal community’s heritage,” says Aimee Keithan, Boothbay Region Historical Society executive director. “It's heartening to see local businesses come together to support our mission, and we're excited to see the impact this fundraiser will have on the society’s programs. We encourage everyone to participate in this raffle by June 8 and help us continue our work of celebrating and preserving Boothbay's rich history." All proceeds will benefit the Boothbay Region Historical Society’s 2024 annual fund.

    In addition to the winner’s private BYOB cruise during Windjammer Days week, Hesper is available for public and private day sails out of Bristol Marine’s shipyard at 120 Commercial St.

    To learn more about the vessel and pilot cutter history, visit Don't miss your chance to set sail on a piece of living history and support a worthy cause.