At the Classic Yacht Owners Association’s (CYOA) Annual Meeting and Award Ceremony in November, members became quite familiar with the name of one of the newest vessels to join their ranks. James Emery’s Lilith claimed the top spot in the CYOA’s Classic Yacht Challenge Series (CYCS) overall Classics division, and picked up a few other awards as well.

“The racing was just right for me, competitive enough without being cutthroat, and fundamentally friendly, with most of us out there to enjoy sailing with other similar wooden boats and classic yachts,” said Emery, reflecting on his first CYCS season.

Lilith raced in nearly all of the 2024 CYCS regattas and the boat and crew instantly ingratiated themselves into the CYOA family. The yacht is a cold-molded replica of the N.G. Herreshoff Buzzards Bay 25 and was purchased by Emery in 2022. This summer, Emery sailed Lilith to Maine from its home port in Annapolis, Maryland for the CYCS.

“With very conservative sailing, and careful attention to the weather, we were able to get up and back without any issues,” Emery said of the passage to and from New England. “I had good help from an experienced crew for those [more difficult] stretches.”

Emery says that the planning required to get Lilith to Maine and compete in the CYCS was well worth it. “If you were to chart the optimum sailing itinerary around New England for July - August, It would be about the same as the CYOA circuit.” To him, the series was a chance to relive the summers of his youth spent sailing New England, and reconnect with close family and old friends in some of the country’s most stunning coastal settings.

Beyond the nostalgia, Emery commended the hospitality of the CYCS host boatyards and yacht clubs that made logistics on arrival a breeze. “Help with moorings, all kinds of other common needs,” were taken care of or made easy throughout the series.

Emery’s advice for anyone thinking about joining CYOA and competing in the 2025 CYCS? “Give it a shot. [The regattas] are all a bit different. You don’t need to have a large boat with a professional crew to do this circuit.” All in all, the juice is worth the squeeze to take part in a series that has become the pinnacle of classic yachting in the Northeast.

Ready to take that advice and become a member? More information on joining the CYOA can be found on our website. Stay tuned in the new year for more information on the 2025 CYCS and other events!