The annual Round the Island Race is a two-day, 100–nautical-mile circumnavigation of Santa Rosa Island. The race begins and ends at the Fort Walton Yacht Club and is typically held each year in either June or September. The event welcomes all multihulls capable of clearing bridges with a 48-foot height or less. Day 1 features a 60-mile race, starting at FWYC, exiting through Destin Pass, sailing along the Emerald Coast in the Gulf of Mexico, entering Pensacola Pass, and finishing at Quietwater Beach near Key Sailing. Day 2 offers a scenic and technical 40-mile challenge through the Santa Rosa Sound and Intracoastal Waterway, returning to FWYC. Participants will enjoy abundant wildlife, crystal-clear waters, and breathtaking scenery, along with outstanding social events featuring food, drinks, and fun. The Regatta Chair is typically the world-renowned sailor and Sailing Hall of Fame inductee, Randy Smyth.