Waikiki Yacht Club was founded in 1944 by a few enthusiastic yachtsmen with grand memories of the excellent sailing and yacht racing in Hawaiian waters prior to World War II. The bombs that fell on Pearl Harbor also destroyed, less dramatically, organized yachting in as non-military craft were banned from the potentially dangerous waters. As the war drew to a close, a small group of sailors began refurbishing their boats that had been left idle for the duration of the war. Their goal—to re-establish yacht racing and to organize a yacht club to support it.
Scouting for a suitable location for the "fleet," the group persuaded the Territory of Hawaii to allow it the use of a small pier in the Ala Wai Harbor, located at the club's current parking lot. As the military began winding down operations in the Ala Wai, the sailors were able to obtain more space and a couple of old Army shacks to serve as the first clubhouse for the newly formed Waikiki Yacht Club.
There were 37 charter members on the rolls that first year. George Over Jr., a driving force behind it's formation, was elected the club's first commodore. The original Board of Directors included Duke Kahanamoku and Dick Soelberg, with other key roles played by John Child, Bob Miller, Art Myhre, and Guy Rothwell.
Waikiki Yacht Club has continued the growth and direction inspired by these founding members. In 1947, the club established one of the first junior sailing programs in Hawaii. This program, still dedicated to teaching Hawaii's young people sailing skills, as well as a deep respect for the sea, has graduated many excellent sailors. Club members Dave McFaull and Mike Rothwell went on to win silver medals in the Tornado class in the 1976 Olympic Games.
In 1978, the club organized the first Clipper Cup Yacht Series, a biennial event that grew into the Kenwood Cup, one of the most prestigious yacht races on the world ocean racing circuit. That series was discontinued in 2002, and was replaced by the annual Waikiki Off-Shore Series, which offers a variety of buoy and distance races.