The 2026 Rolex Big Boat Series Starts Tomorrow

Tomorrow is the start of the 62nd edition of St. Francis Yacht Club’s (StFYC) Rolex Big Boat Series (RBBS). San Francisco Bay’s most prestigious annually held regatta, it will feature three one-design classes (J/105, J/88 and Express 37), four (yet to be distinguished) ORC classes, and a Classics division.

Eighty-nine boats are registered for the event, with racing spanning four days, Thursday through Sunday. The one-design classes have 10 races scheduled — three on Thursday, Friday and Saturday, and a Bay Tour on Sunday.

The ORC fleets have six races planned, with an offshore race on Thursday, two races on Friday and Saturday, and a Bay Tour on Sunday. The classics will race once each day, off the race deck. There will be no shortage of social programming, highlighted by the regatta’s infamous Mount Gay Rum Party on Friday night — keep an eye out for some sailors nursing hangovers on Saturday morning.

ORC

All three of last year’s ORC winners are returning to race. This year’s regatta will also serve as the ORC North American Championship, drawing a larger turnout than normal: 30 ORC boats. One boat to look out for will be Michael Firmin’s Australian Infiniti 52 Zeus (featured on the cover of last October’s edition of Latitude 38), winning ORC A last year, and looking for a repeat victory. The same is true of last year’s ORC B winner (and Rolex winner), Peter Wagner’s vaunted J/111 Skeleton Key program.

Zach Berkowitz’s J/100 Feather has won ORC C the past two years, and will feature 2028 Olympic hopeful Hoel Menard as tactician as the team looks to three-peat.

Other ORC boats to look out for will be Natural Nine, a successful Rogers 46 program from Southern California; Hypatia, a local Solaris 47; Dave MacEwen’s J/90 Lucky Duck; Phyllis Kleinman Swiftsure ORC winner Reverie; and the ever-popular Bill Lee 68 Merlin. 

One-Design Classes

As ever, the biggest one-design fleet in the event will be the hyper-competitive J/105 fleet, which runs 30 boats deep this year, primarily made up of local programs. Of those 30 boats, five have previously won the event with their current drivers. Included in that group is defending champion Arbitrage, helmed by Bruce Stone. They will be without tactician Nicole Breault, as she’s helming the She Wolves’ racing program at New York Yacht Club’s International Women’s Championship Regatta in Newport, Rhode Island.

Two other programs have won Rolexes in this aggressive fleet in the past five years: Ryan Simmons’ Blackhawk program, who have won four of the past six RBBS titles in the J/105 fleet, and Randy Hecht’s Niuhi, who won in 2022, and have won three of the past four J/105 North American titles.

The lineup of past winners is impressive, but there is no shortage of boats that will be looking to claim their first Rolex, and the fleet is deep; nearly half of the fleet can feasibly win a race. With 30 boats, 10 races and no drops, even if a boat jumps out to an early lead, one finish in the bottom third, or a score that involves numbers, could take a boat from first to off the podium. As always, consistency will be the name of the game in this cutthroat fleet.

While the other two fleets, Express 37 and J/88, are smaller than the J/105 fleet, both promise to deliver exciting racing. Mark Chaffey and Heidi Hall’s Loca Motion program have won the past two titles in the Express fleet, and will be looking to make it their third in a row. They will be fighting with eight other boats for that top title.

The J/88 fleet features seven boats, with the team to beat being Brice Dunwoodie’s defending champion program on Ravenette. Speedwell, Inconceivable and Butcher will be boats to watch as they try to dethrone the defending champ.

Classics

The Classics division makes a return to racing this year after their absence in 2025. In 2024, the division was limited to just two boats, so for fans watching from ashore, it will be good to see six large, beautiful wooden boats racing along the Bay. The fleet will start at noon each day off the StFYC’s race deck, and will sail one race.

The six boats racing will be the yawl Ocean Queen V (sailed under the burgee of the Peninsula Youth Sailing Foundation), gaff schooner Aida, Herreshoff gaff schooner Brigadoon, yawl FAIRWYN, ketch Hurrica V, and schooner Wiletie. 

If you’re a sailboat-racing spectator, head down to the Bay this weekend to watch some top-class racing action.