Jessica Cup 2025 & Bay Championship Series
Brigadoon sailing the downwind leg.
Saturday, October 18, 2025, delivered a picture-perfect fall day on the Cityfront for the Jessica Cup, the season-ending classic-yacht regatta hosted by St. Francis Yacht Club (StFYC). Light northerlies at the first gun had skippers hunting for clean lanes and leverage against a building ebb, and the mixed fleet—ketches, yawls, gaff-rigged schooners, Marconi sloops, and more—made the most of it.
Race 1 began in gentle northerlies with fleets fanning out to find pressure and current relief. As the breeze steadied, tidy boathandling paid: conservative starts, patient upwind lanes, and crisp sets and douses made the difference. With flat water, autumn light, and the Cityfront in full view, it was wooden-boat racing at its best.
Crew of Aida heading to the races.
Makani Kai and Sequestor flying spinnakers.
A special thanks to our hosts at StFYC for polished race management and warm hospitality ashore: Commodore Adam Gambel, PRO Tony Chargin, Regatta Chair Terry Klaus, Race Director Felix Weidling, and Race Office Caleigh Thompson.
Classic Wooden Yachts
It was in 1990 that StFYC—at the urging of a committee of classic-yacht enthusiasts—added a new regatta to the calendar to feature classic wooden yachts from earlier decades. A beautiful trophy, donated to the club by the New York Yacht Club in 1984, was repurposed for this regatta. According to S/C Terry Klaus, who played a role in these events, the trophy was named for the daughter of a NYYC Commodore. At some point the daughter, for unknown reasons, fell out of favor with the Commodore—perhaps she beat the old man in a sailboat race—and the New Yorkers sent the trophy to St. Francis, where it has found new life. The first Jessica Cup winner was the legendary StFYC yacht Athene, also the winner of the first Big Boat Series.
Over the years, other types of classic boats have been added to the Jessica Cup. Today there are four classes competing—Farallone Clipper, Gaff, Marconi I, and Marconi II—and the event is part of the San Francisco Bay Classic Wooden Boat Championship. Trophies for that championship were also awarded this year at the traditional post-regatta dinner.
Crew of the Water Witch awarded the Jessica Cup.
2025 Jessica Cup — Results by Division
Marconi I (Over 40 ft)
1st — Water Witch — Jessica Cup Perpetual Trophy
2nd — Kay of Göteborg
Marconi II (Under 40 ft)
1st — Fjaer — Rascal Cup Perpetual Trophy
2nd — VIP
Gaff
1st — Brigadoon — Yankee Cup Perpetual Trophy
2nd — Makani Kai
Perpetual trophies: The Jessica Cup (Marconi ≥40 ft), Rascal Cup (Marconi <40 ft), and Yankee Cup (Gaff) are the three historic perpetuals awarded for this regatta.
Bay Championship Series — 2025 Award Recipients
Marconi I: Water Witch — John & Gena Egelston
Marconi II: Cuckoo — Bill & Kathleen Claussen
Gaff: Brigadoon — Terry & Lindsey Klaus