The Southernmost Regatta 2026 returns to Key West, Florida from January 19–23, 2026, bringing together elite sailors and enthusiasts for five exhilarating days of racing and island festivities. Powered by Sailing Inc., this prestigious event blends high-level competition with the laid-back spirit of the Florida Keys, making it one of the most anticipated winter regattas in the United States. The event is open to One Design and ORC Racing / Cruising Keelboats. Our plan is to provide a two races a day on two course, a One Design Course and an ORC Course. We will also offer one distance race a day for ORC cruisers.