October 13-14: The Yacht Club of Hilton Head Island Regatta Weekend 2018! The Harbour Town Cup: Saturday, 12 p.m. start. The Calibogue Cup: Sunday, 10 a.m. start. Since the 1970s, The Yacht Club of Hilton Head Island has held two sailing race events in Calibogue Sound. Spectators are welcome and volunteers will be in Harbour Town to explain the races. Come enjoy a great day in Harbour Town viewing the races, shopping and dining. Registration required, (843) 384-7322.