The Southernmost Regatta

Experience world-class sailing in paradise at The Southernmost Regatta, January 20–25, in the turquoise waters off Key West, Florida.
This premier international event unites top racing teams from around the world for five thrilling days of high-caliber competition set against the stunning backdrop of America’s southernmost waters.

Open to One Design and ORC Racing/Cruising Keelboats, the regatta features two races per day across dedicated courses—including the J/111 North American Championship, plus competitive action in the J/70 and ORC Performance classes.

The Southernmost Regatta celebrates everything that made racing in Key West legendary: blue-water sailing, island camaraderie, and the chance to reconnect with friends during the winter months. Racers and spectators alike enjoy steady January breezes, warm tropical waters, and the lively spirit that makes Key West unlike anywhere else.

With more than 30 years of sailing tradition, racing in Key West has become more than just a competition—it’s a way of life. Whether you’re on the starting line or cheering from shore, The Southernmost Regatta delivers world-class racing, island hospitality, and unforgettable moments on and off the water.

Join us this January and be part of a Key West tradition where championship sailing meets the beauty and charm of the Conch Republic.