San Francisco Bay is famously windy. It was true when the windsurfing worlds came to San Francisco in July 1983, and it was true during this past weekend’s Master Mariners Memorial Day Weekend Regatta. It was also sunny, and there’s no better weather combination for sailing and classic-boat races than wind and sunshine.

Forty of the Bay’s classic wooden vessels signed up to race in the modern tradition of this annual regatta that has been held since Lyndon Johnson was president in 1965. The boats were split into nine classes, featuring rigs that are less common and less well known. There was a class for schooners, for Marconi and for gaff-rigged boats. There were one-design classes for Birds and Bears. There was no such thing as sportboats — plastic classics were all built decades after most of these boats started sailing.

The race starts off the St. Francis Yacht Club, with the Sausalito Yacht Club running the starts from their committee boat. The traditional course takes boats on a reaching start to Little Harding, where classes split to Easom or Blackaller before heading east to Blossom Rock, and then off to the Bob Klein mark by Southampton Shoal before finishing behind Treasure Island. Following the finish, the fleet starts to strip off the foul weather gear as they head southeast down the Oakland Estuary toward the post-race party at the Encinal Yacht Club.

As the morning fog backed off and the wind picked up, the Bay was choppy with the soon-to-be-fading ebb. To keep it all interesting, the pre-start included dodging boats heading out for the SSS Singlehanded Farallones race and 420s sprinting down the waterfront under spinnaker. A large, unique-looking Japan coast guard ship also passed through the fleet. The Bay was brilliantly lit and freshly filled with all kinds of sailing activity.

The sailing between the start and finish was a feast for anyone who appreciates the beauty and heritage of wooden classics and a muscular, tactical, strategic challenge for the crews working hard to manage these classics around the mostly reaching course. We were sailing aboard the beautiful Stone Boatyard-built Marconi cutter Water Witch, which has been lovingly restored over the past 25-plus years. Like most of the boats in the fleet, she is the beneficiary of years of caretaking, but they’re all pushed hard when there’s a trophy to be won.

Water Witch is the scratch boat, meaning she’s fast and starts last in this reverse-handicap event. Since we were guests, our primary role was rail meat, which allowed us to ogle all the boats and take some pics as we made our way toward the front of the fleet. The primary crew were skipper John Egelston,  aided by son Andrew managing the big mainsail and runners; Master Mariners commodore Gena Egelston, who gave logistical support for the boat and the whole event; Laurence Bekins on jib trim; Dave Williams and Madeline Morey in cockpit; Phil Mills on the foredeck; and Ray Lynch calling tactics.

We watched the Bird and Bear boats head off first, then schooners, ketches, yawls, sloops and cutters, some of them gaffers. Brigadoon, Hurrica V and Freda are now over 100 years old, and all powered through the blustery day in fine form with wind gusts approaching 30 knots. Water Witch will join the century club in 2028, and felt as solid as (we imagine she was) the day she was launched. To the best of our knowledge, there were no broken spars, blown sails or other carnage among the fleet, which is a testament to the designs, the builders and the current owners, along with the amazing building material called wood. And as our good friend Woody says, not many yacht races — other than the America’s Cup — can claim a history stretching back 175 years. But San Francisco’s Master Mariners Regatta, at 159 years, comes remarkably close. And the 102-year-old, 65-ft schooner Brigadoon, skippered by Lindsey Klaus, has raced 49 consecutive Master Mariners regattas and took first place in her class!

The race was not without drama, with one incident being a woman overboard from our own ride, Water Witch. One of the features of the boat is that her elegant lines are undisturbed by lifelines, and her low freeboard keeps you close to the water. On our jibe near the Bob Klein buoy, fellow rail-rider Elena Stephens was caught in the deep water running down the new leeward rail and was swept astern. We were moving fast, so we separated quickly. She waved to signal she was OK, and as we maneuvered to line up a challenging recovery effort, a powerboat shadowing the race saw our signals and was able to follow our pointing to pick Elena up. We were able to reconnect with Elena at the Encinal Yacht Club.

Encinal Yacht Club offered Estuary magic with warm, calm and welcoming docks for the annual fleet raft-up. As the boats tied up, the sails were furled and the boats dressed ship, with winner’s flags from numerous past regattas adding to historical flags and sponsor flags. Add in the live band singing sea chanteys, and the stage was set for a lively dinner and awards ceremony ashore.

Sailing the Master Mariners Regatta on classic wooden boats is a powerful reminder that it isn’t ease and comfort that make sailing so compelling. There’s art, beauty and elegance, all balanced with the physical and mental challenge of maintaining, sailing, and sometimes winning, among a friendly, competitive tribe of wooden-boat lovers all drawn by a powerful magnetism that keeps bringing people close to classic-boat sailing.

See the full results here.

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