Started in 1966, the race has been held in memory of Past Commodore Ed Willman of the Key Biscayne Yacht Club. The Round the Island Regatta is a fun, competitive event that engages sailboats of all sizes in a race from the waters of Biscayne Bay in front of the Key Biscayne Yacht Club, south through the Stiltsville featherbeds and past Cape Florida, north along the Atlantic coast of Key Biscayne, around a mark at the opening of Bear Cut at the north of the island, and back to the Key Biscayne Yacht Club.