Begun in 2013, it is an annual sail and powered boat race in commemoration of the races run off the clubhouse deck in the '60s and '70s. In those days the membership could enjoy and participate in both the start and finish of the races.

The divisions are Spinnaker, Non-Spinnaker, and Powered boat Predicted Log. The sailboat races are pursuit races, so called because the slowest boats start first and are “pursued” by the faster ones. This race is intended to be a fun event, bringing together the full range of our membership to witness and even engage in cheering on a favorite from the comfort of the club's lounge and dining room. The race is open to everyone and free for SYC members.

The Perpetual Trophy was donated by life member Charles “Bud” Livingstone who got the jaws from his family's summer resort in New Hampshire where the jaws were on display from 1930 until 1983. Its provenance is a little mysterious in that one story claims the 10-foot blue shark was wrestled into a boat in Cuba by the donor and his fishing buddies; another version was that it was purchased at auction by Bud's father to add to the Livingstone Lodge antiques and curio collection. The race is typically held mid March.

The WINTER TROPHY for the races commonly known as the Midwinters was created by the SYC in 1981. Recognition is given to the winners of each division in the Series. These races are held once a month November through March. The winter sailing conditions are typically lighter air coming from the land than summer conditions and often involve more extreme tides.

Presented by then Rear Commodore Frank Z. Mora in 1979. The Rear Commodore's Trophy was originally awarded to the winner of a special “race-cruise regatta” from the Sausalito area to Vallejo, usually held during the July 4th weekend. In 2022 this race was changed to a Pursuit-race format within the central bay.

Presented in l98l in memory of SYC member, Ben Blum, The Blum Trophy is awarded to the best placed SYC member in Division A for the combined Sunset Series.

The Gear Trophy is awarded to the to the best placed SYC member in Division C for the combined Sunset Series. Presented in 1984 by SYC Senior Member, Miggs Gear.

Presented in 1986 by Rear Commodore Gilbert Oliver and Bonnie Oliver. The Oliver Trophy is awarded to the best placed SYC member of Division D for the combined Sunset Series.

The Twin Island Regatta was conceived in 1979 as a race around the two islands, Angel and Alcatraz, in either direction. The race was to be held on the day before opening day, usually the last weekend in April. Then-chef Fernand Loing, had the Twin Island Trophy created to have the best finishing SYC member engraved on it. This resulted in the sometimes used nickname “The Chefs Special”.

Today the Race has two divisions, spinnaker and non-spinnaker. It starts from a Race Committee boat in the Knox area off Angel Island, then a port rounding of a buoy by Yellow Bluff after which the skippers choose to round the two islands clockwise or counterclockwise, back to a starboard rounding of the Yellow Bluff buoy, and a finish off the club race deck.

In 2003 Rod Decker, a SYC member and racer, proposed adding a trophy to the Twin Island Regatta by creating a series adding two more races, one in the summer and one in the fall. He presented the Decker trophy to the club for the best overall SYC member finishers of the three races to be engraved on it.

This trophy was deeded to the club by Staff Commodore John Williams in 2017 on the 75th anniversary of the founding of the Sausalito Yacht Club. It will be awarded to the winning youth (under 18 years of age on the day of the race) in each division of the Twin Island Series with the best series record of scored races.

Originally called the Lady Skipper's Trophy, the Women Skippers Regatta Trophy was presented by the SYC Auxiliary in 1980 to the winning skipper in each division, regardless of yacht-club affiliation.

An additional trophy, the Womens Skippers Race Trophy, was added in 2002 to be awarded to the first place SYC boat in each division.

This trophy is awarded to the winning all-female crew in the Women Skippers Regatta. Designed by Gail Ward, it was donated by the SYC Auxiliary in September 2006 in order to encourage all-woman teams to participate.

Presented in 1984 by Commodore Craig Brown. The Commodore's Trophy is awarded annually for distiguished service on the Board of Directors and for outstanding involvement in racing activity.

Presented in 1981 by founding members, Jim Enzensperger and family. The Enzensperger award is for distinguished service to the SYC.

Presented in 2003 by a founding member of the Sausalito Yacht Club. The Peggy Plumley Trophy is to be awarded to an individual associated with SYC's Youth Sailing Program for rendering distinguished service.

The Shirley Bates Perpetual Trophy was gifted to the Sausalito Yacht Club by Commodore Mary Richardson in November of 2008. This trophy was created in recognition of the significant contribution to Bay Area sailing made by SYC member Shirley Bates.  A member of SYC since 1957, Shirley has sailed and raced with vigor and tenacity in San Francisco Bay events, always maintaining the highest level of sportsmanship.  As the first recipient of this Trophy, Shirley Bates has set a standard for future recipients.  The Trophy will be awarded not more than once per year to an SYC member who is recognized by the Race Committee as having made a significant contribution to San Francisco Bay sailing. This includes contributions in all aspects of sailing, racing, cruising, junior sail training and other sailing related activities.  The Trophy will be kept on display at the Sausalito Yacht Club. Each recipient’s name will be engraved on the plaque of the Trophy. A token of the Trophy (keeper) will be award to each recipient at the Annual Race Banquet or the SYC Annual Membership meeting.-