Master Mariners San Francisco Bay · Est. 1867
Archive Notice: This is an independent historical archive. Not affiliated with the Master Mariners Benevolent Association (MMBA) or any successor organization.

The Jessica Cup Regatta

Autumn racing for gaff-rigged and traditionally designed yachts · St. Francis Yacht Club

Jessica Cup Regatta

The Jessica Cup is the MMBA's annual autumn regatta, hosted by the St. Francis Yacht Club on San Francisco Bay. While the main Memorial Weekend regatta is open to a broad range of traditional vessels, the Jessica Cup is specifically designed for gaff-rigged and traditionally designed yachts — celebrating the older rigs and construction methods that define the MMBA's spirit.

Notice of Race — Key Details

Race Day Schedule

Racing concludes with a trophy ceremony recognizing fleet winners. Following the ceremony, competitors and their guests are welcome to attend a Banquet dinner at the St. Francis Yacht Club. Trophies are awarded in accordance with fleet size.

Entry Requirements

An entry fee is required with the return of the Entry Form by the Wednesday before the race. A discount is available for entrants who provide proof of US SAILING membership.

About the Gaff Rig

The gaff rig — characterized by a four-sided mainsail supported by a gaff spar on its upper edge — was the dominant sail plan for working and cruising vessels through the 19th century and into the early 20th. The Jessica Cup celebrates this tradition, bringing together boats that connect the Bay's modern sailing community to its maritime heritage.

Classic gaff-rigged vessels on San Francisco Bay range from small catboats to ocean-going schooners, and the Jessica Cup draws them all to the starting line on the City Front.

St. Francis Yacht Club

The St. Francis Yacht Club, located at the Marina Green in San Francisco, has hosted the Jessica Cup and served as the start/finish for the main Master Mariners Regatta for many years. Its location at the edge of the Bay provides an ideal launching point for racing in the Central Bay.

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