2026 Master Mariners Memorial Day Regatta

Strong winds, tight finishes, and a rooster flag ten years in the waiting.

On Saturday, May 23, the classic fleet gathered on the city front for the 2026 Master Mariners Regatta, and the Bay delivered the kind of day this race is famous for: cold, building breeze, a short chop, and gusts near thirty knots by mid-afternoon. Nine divisions raced. Everyone got wet. Nobody seemed to mind.

Five Bears led the fleet off the line at 12:15 — a fine turnout for the Bay's venerable one-design class — with the rest of the divisions following at intervals, slower boats first, in our traditional pursuit format. The course ran from the city front out around the Bay and home to the finish east of Treasure Island, by way of the Hank Eassom mark, Blossom Rock, and the Bob Klein mark, where the breeze was at its meanest.

The clock did its work all afternoon. In Gaff 1, Brigadoon turned in an elapsed time of 1:55:38, believed to be the fastest ever sailed in the division. In Marconi I, the day's deepest fleet at nine boats, Ocean Queen and Hurrica V finished barely three minutes apart. Magic led the Bears home, Kaze sailed away with the under-30-foot honors, and in Gaff 2 came the finish of the day: Black Witch crossing three seconds ahead of Makani Kai. Makani Kai's faster elapsed time earned her the Kermit Parker Trophy; Black Witch, first across, took the class — and her first rooster flag in more than ten years.

Aboard Black Witch: "She lifted her skirts and ran"

This was the fifth try at the Gaff 2 flag for Black Witch under steward Sandee Swanson. The sloop has sailed this regatta for more than fifty years and won plenty, but a win had eluded the current crew — who, as it happens, met as a team for the first time on Saturday morning. They knew the boat well, though: Craig and Julian, the father-and-son woodworkers who laid her decks twenty years ago; Sydney, her new rigger, fresh off running six hundred feet of new running rigging this spring; and Capt. Stan, on the helm these past five years.

They were wet before they ever reached the start. Out in the Sausalito channel the captain called for a double reef in the big main — no small job under a twenty-five-foot boom — and tucking it in off Hurricane Gulch was the new crew's first task together. The second came at the worst possible moment: practicing maneuvers before the start, they lost the mainsheet. Sydney took charge — main down, into the boom gallows, re-rig — and they crossed the line a minute late, glad to be racing at all.

From there, in the crew's words, the Witch "lifted her skirts and ran with all her might." They tacked out for pressure at the Hank Eassom mark and got the puff they were praying for to round it clean. At Bob Klein the gusts hit thirty — measured the old-school way, since Black Witch carries no instruments, just a handheld and thirty years of Bay experience at the helm. On the run to the finish Makani Kai came hunting and looked to take them to windward, but Capt. Stan wasn't giving it up. Three seconds. Their goal, based on four prior attempts, had been to sail the course in 2:30. They beat that by four minutes — and beat everything else in the class to the line.

Aboard Kaze: choreography in the cabin

In Marconi IV, Liz Diaz had Kaze prepared for victory and her crew prepared for, as one first-time Master Mariners racer aboard put it, "choreography in the cabin and role adherence — a.k.a. do what the Captain says." It worked. Kaze sailed a clean, quick race to win her division and the Lyle Galloway Trophy for best elapsed time under thirty feet — sweeter still because the Proudfoots, who donated the trophy, are friends of the boat. "Just to be out on the Bay in the midst of those magnificent boats would have been more than enough," the crew reported. "Grateful to Master Mariners, the weather gods, and all who came to play."

Ashore at Encinal

As the racing wound down, the fleet made its way to Encinal Yacht Club for the raft-up, dinner, and awards. Doug Closson's Sea Shanty Band greeted arriving crews with maritime tunes as the docks filled, and awards went to the top three finishers in all nine divisions, with rooster Champion flags to the class winners.

For some, the evening was the discovery of the weekend. "That was the first time I ended up at the club after the race," one skipper wrote afterward, "and I can't believe I haven't done that previously. What a cool vibe, especially at night at the dock — everyone's out singing sea shanties and having a fun time." Many crews stayed the night and sailed home Sunday after the potluck breakfast, the traditional close to the best weekend on the classic calendar.

Thank you to our Race Committee, our sponsors, and every volunteer afloat and ashore who made the 2026 Regatta a day to remember.

Full results are posted on the Master Mariners Regatta page.