custom, bespoke windjammer voyages

Experience Maine as we would. This is windjamming, but different. Custom curated private voyages aboard the Pilot Cutter Hesper, a 60’ Gaff Rigged West Country Cutter meant to cross oceans. Beat the crowds and travel safely. A farm to boat experience, there is no better way to experience Maine

Sail. Explore. Relax

Join us for our overnight windjammer cruises, full day lobster bakes, regattas and other private charters out of Camden Maine. Become part of the crew, learn to harness a 25 ton wooden gaff cutter, or sit back and vacation at your own pace.

Follow us on instagram @Pilotcutterhesper

One of our favorites- Hesper prowling around Brooklin in the fog. Shot by @tylerfields_photography
Hanking on the jib topsail before race day. Notice the great bow details and planking. 📸 @magic_sites
Starting line, @eggemogginreachregatta 📸@magic_sites
On August 6th, in a fleet of over 100 boats, full of Fifes, Alden’s, Herreshofts, one designs and numerous other classic, white wooden sailing boats, Pilot Cutter Hesper took home the Mendlowitz Award for ”Most photogenic boat”. Mar