Carrying a legacy forward

Published on September 30th, 2025

by Jay Smith, SpinSheet
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. – Full report

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