Sailboat Racing in a One-Design Fleet Across Generations: the Cal 25
There’s a special allure to discovering a sailboat that has navigated the Chesapeake Bay for decades, its competitive spirit undimmed. In Annapolis, the Cal 25 fleet stands as a testament to this enduring legacy. This tight-knit group of classic one-design boats and passionate sailors has preserved the essence of authentic racing for generations.
Designed by C. William Lapworth in 1965, the Cal 25 quickly rose as a premier one-design racer, even hosting a National Championship in its first year. Just three years later, in 1968, the Chesapeake Bay Cal 25 fleet was formally organized, beginning an unbroken tradition of racing on these waters. In 1971, Annapolis hosted its first Cal 25 Regionals, and by 1978 the fleet welcomed its first Nationals, firmly establishing Annapolis as one of the class’s strongest homes. Fittingly, High Proof, the Cal 25 I now co-own, was launched in that founding year of 1968, tying today’s racing directly back to the fleet’s earliest days.
But history isn’t just written in championships and milestones; it lives in the people who made the fleet what it is. Even as a newcomer, I felt the influence of legends such as Charlie Husar, remembered for his devotion to the fleet and legendary mixed drinks. That spirit lives on in today’s Cal 25 sailors: competitive on the water and generous on shore.
The character of the fleet is reflected in the boats themselves. More than half a century after their launch, Cal 25s are still lining up on the starting line, proving that solid construction and smart design can outlast trends. By modern standards they may lack high-tech flash, but they reward skill and seamanship, keeping racing both affordable and accessible.
I had no knowledge of the Cal 25 before climbing aboard one for the 2024 AYC Hangover Bowl. On that foggy New Year’s Day, I was completely green and relied entirely on the patience of the crew aboard Arctic Tern. The thrill of that first race hooked me. Since then I’ve logged more than 30 starts-including a first-place finish in this summer’s EYC Beer Can Series.
This summer, a friend and I took on the shared ownership of High Proof, a 1968 Cal 25. Restoring her has been a hands-on education in boat ownership, made possible by splitting responsibilities and leaning on the generosity of fellow fleet members, who offer spare parts, stories, and always a helping hand.
That mix of history and affordability makes the Cal 25 a perfect entry point for racing, but the fleet needs new energy to carry it forward. Our boats may be scattered across creeks and coves, but when it’s time to race, they still turn out. What we need most now are fresh captains and curious sailors ready to join the starting line and keep the tradition strong.
If you’ve ever thought about owning or racing a classic boat, now is the time. There are boats looking for skippers, crews eager to sail, and a tradition worth keeping alive. Age and experience don’t matter; what matters is showing up with a willingness to learn and race hard. The Chesapeake is calling, and the Cal 25 fleet is ready for its next generation.
To learn more, reach out to the Cal 25 fleet captain, Alisa Finney, at [email protected].
~By Jay Smith
