Photo: Ray K. Saunders

NANTUCKET, MASS.— The weekend of August 15-17 featured beautiful conditions with strong winds for the Nantucket Regatta and the Opera House Cup both hosted by Nantucket Community Sailing and part of the Classic Yacht Challenge Series. Along with exhilarating classic sailing, the regattas brought out island visitors and residents alike to take in the action.

“The CYCS returned to the Massachusetts Islands in style last weekend with strong winds and tight racing in Nantucket,” said CYOA Chair Timmy Dittrich. “The final regattas of the 2025 season are on the horizon, and it’s exciting to see how the competition is shaping up.”

“Conditions were definitely sporty this weekend,” said Diana Brown of Nantucket Community Sailing. “From the Classic Yacht Exhibition to the parade of wooden boats to the racing itself, this was a gorgeous weekend of sailing for both competitors and the Nantucket community. A crowd of over 1000 people watched the parade from Jetties Beach and heard about each competing yacht. We were proud to welcome non-wooden boats to the Opera House Cup this year with our Invitational Division.”

Peter Cassidy’s 1936 S&S 45 Siren topped the podium in the Vintage Division and took the second spot overall. The 1938 Sparkman & Stephens Black Watch took top honors in Division 1 for the Nantucket Regatta - all about securing the top spot in the CYCS overall. 

The Gwen Gaillard Spirit of the Race Award, named for the Opera House Cup’s founder, was awarded posthumously to Jesse Terry of the 1956 Alden 39 Abigail.

Full results for the Nantucket Regatta and the Opera House Cup can be found on the Nantucket Community Sailing website. 

In the Massachusetts Division of the CYCS, Siren (Peter Cassidy) led the Vintage class with 271.43 points, followed by Gentian (Ben Sperry) at 263.33; Outlier (Harvey Jones) topped Contemporary with 300 points; and Juno (Scott DiBiaso) claimed Classic division with 280 points.

The next stop in the CYCS will be Bristol, R.I.’s Herreshoff Classic Yacht Regatta held from August 22-24. The classics fleet is set to take over Narragansett Bay for the event, which features feeder races both to and from Newport.

“Celebrating the care and feeding of classic yachts is a concept that lies at the heart of the Herreshoff Marine Museum’s mission, and the museum has been holding the Herreshoff Classic Yacht Regatta each August for over 40 years,” said regatta organizer Bill Lynn. “The Herreshoff legacy makes this event much more than a regatta - it is truly a ‘gathering of the faithful’, and participants come to Bristol to enjoy both great racing and the camaraderie of their fellow classic yacht enthusiasts.”

The Herreshoff Regatta will be followed by another Narragansett Bay regatta before the season wraps up in September in Long Island Sound. Current Standings in the Series can be found on the CYOA website.