One of our favorites- Hesper prowling around Brooklin in the fog. Shot by @tylerfields_photography

A blazing red sunset from the other night. Isn’t fall the best? There’s still time to book a private charter and experience this. 📸 @sweetkiwipete

🌅 August Sunsets 🌅

Hanking on the jib topsail before race day. Notice the great bow details and planking. 📸 @magic_sites

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Just listen and relax…..

Cinematically tacking Hesper into fall weather and the end of our season.

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”. Marine photographer Benjamin Mendlowitz, publisher of the Calendar of Wooden Boats, and marine historian Maynard Bray, who has provided the text for the Calendar since its inception, select the winning boat. Their objective is to recognize one boat, regardless of its racing record, that stands out as an ideal example of the aesthetics, design, fine craftsmanship and commitment to maintenance that are the hallmarks of an exceptional wooden boat. This awards means a lot for many reasons. In many ways Hesper helped save me- she has taught me many tough lessons the past 2 years (and still continues to). She helped create a complete paradigm shift in my thinking on care, and really what it takes to operate a wooden traditional vessel. She also works for a living, going off and on the dock 3 times a day, 7 days a week. In the past two years she has done 248 private charters- I have been at the helm for every single one of them. She does not sit at the dock every day and get painted and cared for by professional caretakers. She gets used, sailed, tacked, climbed on and pooped in. And when we get a moment, just a breathe in between trips, we sand, varnish, paint, oil and tar. I do these things without a second thought- because I like doing them now. I do it because Hesper is a very kind boat and she takes care of me, so I do the same for her. We have big things planned for the future which we are excited to share with you this fall, but for now I’ll leave you this photo of Hesper, built by @workingsail , in 2004, Greek Quay. 📸 @magic_sites

Brilliant Maine August Sunsets. 🌇 📸 @sweetkiwipete

Canvas + Pine windjammer Sailing Expeditions