The Yesteryear Regatta, first called the Spring Regatta, was organized in 1975 by California Classic boat enthusiasts Bill Clark, Doug Smith, and Bob Spriggs. They later founded the Ancient Mariners Sailing Society in 1976 to promote the enjoyment of classic boats.
Today, the AMSS consists of more than 100 dedicated owners of classic designs that seek to preserve interest in racing, restoration, seamanship, and maritime history. They typically host four events each year including the Yesteryear Regatta. The pursuit-style race features six classes: Classic A, Classic B, Classic C, Pacific Class (Spinnakers allowed), Split Rigs and an L-16 Class. The boats run a 12 mile course through San Diego harbor.