The Southernmost Regatta

The Southernmost Regatta, powered by Sailing Inc., is a five-day sailing event held in Key West, Florida. Scheduled for January 18–22, 2027, it welcomes One Design and ORC racing and cruising keelboats for competition on the area’s blue waters. The regatta’s stated mission is to create a fun, sustainable event that combines high-quality racing with social activities and brings sailors and industry partners together in a welcoming environment.

The program is planned to include two races each day across separate One Design and ORC courses, as well as one daily distance race for ORC cruisers. Beyond competition, the event emphasizes the Key West island experience and opportunities for sailors to reconnect during the winter season. Its approach is described as getting back to the basics of what made racing in Key West memorable, while renewing the tradition on a smaller scale.

The regatta website provides race information, registration, entry lists, logistics, launch and retrieval details, dockage information, and news and results.