Rolex Big Boat Series 2026

Fairwyn racing in the 2026 Rolex Big Boat Series. Photo: ROLEX / Daniel Forster.

Classics and the Next Generation

Six wooden yachts returned to the Rolex Big Boat Series classics division after a year’s absence, sailing one handicapped race each day. With starts and finishes off the St. Francis Yacht Club race deck, spectators could follow the fleet at close quarters.

Richard Leland’s Fairwyn took second in the opening race, then won the next three to secure the series. Ocean Queen V, sailed by young people from the Peninsula Youth Sailing Foundation, won the opener and finished second on each remaining day. Wiletie completed the podium, with Hurrica V, Aida and Brigadoon also racing.

Congratulations to all six crews. The young sailors’ success aboard Ocean Queen V gave this gathering of classic boats a welcome glimpse of its future.

Read Brandon M. Mercer’s Classics Go Full Send in Rolex Big Boat Series for a firsthand account from aboard Wiletie, and visit the official results page.

Source: Latitude 38, October 2026, “The 2026 Rolex Big Boat Series,” classics section, page 48.

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