Windsurfer Fleet 18 was founded in 1973 by Skip Harrison, Mike Horgan, and Glenn Taylor. (Skip Harrison of Napa began selling sailboards in 1970.) The first Fleet 18 race had 50% of all known Bay Area sailboard owners in attendance, there were 6 entrants. By 1980 some Fleet 18 races were drawing more than 100 entrants. In the early 1980's some Tuesday practice events in Foster City had more than 60 entrants.

From 1974 until 1985 Fleet 18 ran an annual race that started at the St. Francis YC in San Francisco, went around a mark near the Coast Guard station, then went on to Ft. Baker on the Marin headland near the north side of the Golden Gate Bridge. An hour later a return race was held between the end of the Ft. Baker pier and a buoy placed a hundred feet off the St. Francis beach. Crossing times dropped steadily over the decade for all classes of sailboards entered. Since the race was conducted in two separately started sections it was possible to discover which sailors had done well on upwind sailing (to Marin) and which had done best on the broad reach course back to San Francisco. In 1985 in the unlimited equipment division Robbie Naish set a record of 13m.25s. from SF to Marin and accomplished the return in 6m.5s. (approx 22 mph). The records for Windsurfer One-Designs set that year were: 17m.8s. to Marin and 9m.16s. to return. The latter time was posted by Ted Huang, who did not use a harness. (In 1996 Ted competed in the Olympics, sailing for the country of Taiwan. He placed 9th.)

The recent history of Fleet 18 has seen a decline in the total numbers of entrants in events. Sailboard shops and schools have all ceased to support racing and social events that encourage amateurs and beginners. For this reason the total number of sailboard sailors has declined in the past twenty years along with the availability in retail stores of craft most suited for one-design racing. Enough equipment still exists in garages and sheds around the greater Bay Area that those who want some sailboard racing experience can participate on used equipment for very little initial expense.