The Master Mariners Regatta is a fitting name for one of the oldest, most challenging and beautiful races on San Francisco Bay. It’s the day when the grand dames of San Francisco sailing come out to play and it’s stunning.

The regatta can trace its origins back to 1867 when a San Francisco race was staged between large coastal schooners and sailing scows. Today all forms of classic sailboats are represented: historic schooners, M-class sloops, Farallon Clippers, L-36s, Folkboats, Birds, Bears, Whaleboats and more.

There is something poetic in watching these graceful classics race, canvas sails flying. It’s maritime history on parade.

The skilled photographers of norcalsailing.com covered the race start and our race photos are courtesy of them, many thanks.

A large raft-up at Encinal Yacht Club follows the race. It’s quite a logistical feat, but the EYC officers and staff met the challenge beautifully.  EYC commodore Susan Jacquelin warmly greeted boats as they arrived.

She looked quite stylish in her classic Saint James shirt. Indeed, there is nothing like a mariniere for effortless nautical style. You can read about the origins of the very chic French sailor shirt here.

And That’s Jazz providing traditional Dixieland music while periodic canon fire signaled the first boat over the line in each division.

We took the opportunity to mingle and learn a little more about these exceptional sailboats.

Brigadoon, a beautiful 65’ schooner designed by L. Francis Herreshoff and built in Massachusetts in 1924, is breathtaking. She was brought to the Bay Area in 1940s by none other than Sterling Hayden. As a classic movie aficionado, I was particularly intrigued. Film noir fans will know him from the classics Asphalt Jungle and The Killing.

Since 1976 Brigadoon has been in the Klaus family, owned by Terry Klaus and skippered in Master Mariners this year by his daughter Lindsey. Congratulations to Lindsey, Brigadoon won her class!

Another beauty, and newcomer to the Master Mariners, is the classic yawl Legend. She has recently relocated to San Francisco from Charleston, SC where she raced in all the East Coast classic regattas.

Her owner, Tim Mullins decided to bring the Sparkman & Stephens designed, Abeking and Rasumssen built classic West to be closer to his Alexander Valley winery, Balo Vineyards. Sailing and wine… I’m seeing a future article now.

Legend made quite an entrance, winning her class.  Although captain Danny Antonopoulos has helmed her for 37 years, many of the day’s race crew were new. She makes quite an elegant statement with her bewitching black hull.

Ian Rogers who crewed on Sunda, his father Bob Rogers’ lovely 1941 Ben Seaborn design, joked the name was really Sunday but there was no room on the y on the slender transom before explaining she was really named after the Sunda Strait in Indonesia.

Morning Star was another female-helmed boat, Barbara Ohler skippering the appealing 47’ classic once owned by Tommy Smothers of Smothers Brothers fame.

Makani Kai, lends an exotic air as a 40’ Angelman ketch built by Pacific East Boatworks in Kaohsiung, Taiwan in 1970.

It’s awe-inspiring to watch these majestic boats to battle in the race then later get a close up look at their handsome, historic lines at the raft-up. The Master Mariners is a must for anyone in the Bay Area who appreciates classic design, or beauty in general.