A long-standing Miami tradition, the Columbus Day Regatta gathers sailors of all levels for a weekend of friendly yet competitive racing on beautiful Biscayne Bay. With a festive atmosphere on and off the water, it celebrates the joy of sailing and Miami’s vibrant maritime community.

The M32 World Championship brings world-class sailing teams together for a spectacular week of high-speed competition on Biscayne Bay. Hosted at Shake-A-Leg Miami, the event combines cutting-edge performance, teamwork, and the unique energy of Miami’s sailing scene.

The Melges 20 and VX One fleets return to Coconut Grove for a weekend of fast-paced, tactical racing. Known for close competition and exciting finishes, this regatta showcases the skill and precision of some of the most dynamic one-design sailors in the sport.

The prestigious Louis Piana Cup gathers top Etchells sailors for a weekend of elite competition hosted by Biscayne Bay Yacht Club. With ideal sailing conditions and a long tradition of excellence, it’s one of the most respected regattas on the circuit.

The Orange Bowl Regatta is one of the world’s premier youth sailing events, welcoming hundreds of young sailors from around the globe. With Miami’s warm winter winds and vibrant energy, it’s an unforgettable week of competition, learning, and camaraderie on Biscayne Bay.

The M32 Miami Winter Series kicks off at Shake-A-Leg Miami with the first regatta of the season. High-performance catamarans, skilled crews, and Biscayne Bay’s perfect racing conditions set the tone for an exhilarating start to the championship series.

Honoring the legacy of Sid Doren, this classic Etchells event brings together top sailors for a weekend of intense and tactical racing on Biscayne Bay. Hosted by BBYC, it’s a highlight of the early winter sailing calendar.

The Bacardi Winter Series combines top-tier competition with unmatched hospitality. Hosted at Shake-A-Leg Miami, the event features world-class sailors and the signature Bacardi spirit—where racing excellence meets social connection.

The second act of the M32 Miami Winter Series takes place right at the heart of Biscayne Bay — high-speed catamarans, elite teams and close-quarters racing create a season-defining event. With perfect winter sailing conditions and a vibrant Miami audience, this regatta is as much spectacle as strategy.

Two dynamic one-design classes meet on the bay for a weekend of tight racing, tactical decisions and thrilling starts. The Melges 20 and VX One fleets bring a mix of experience and innovation to the race course, while Coconut Grove’s waterfront setting adds local charm and community appeal.

Held during the vibrant Coconut Grove Arts Festival weekend, the Etchells Midwinters East regatta combines high-level sailing with cultural energy on the bay. Top Etchells crews race against rising competition while spectators enjoy art, food and water views — a rare blend of sport and lifestyle.

The second leg of the Bacardi Winter Series brings together competitive fleets in a social and festive atmosphere. From serious racing on the water to lively après-sail gatherings, this weekend offers sailors and supporters alike the best of Miami’s bayfront lifestyle.

The Melges 20 class returns for an intense regatta weekend, featuring seasoned crews, emerging challengers and Biscayne Bay’s unpredictable breeze. With Coconut Grove as the backdrop, this event stands out for its mix of performance racing and community engagement.

The iconic Bacardi Cup marks a highlight of the season—elite sailors, international competitors and Biscayne Bay’s stunning backdrop converge for multiple days of competition. It’s a true centerpiece event that blends world-class racing with the hospitality and heritage of Miami’s sailing community.

The third stage of the M32 Winter Series pushes teams to refine tactics, sharpen speed and battle for position as the season builds. Expect close finishes, high winds and dynamic racing in a venue known for its competitive edge and scenic setting.

This longstanding Etchells event draws top crews for a concentrated weekend of intense competition. The Coral Reef Cup emphasizes one-design purity, tactical racing and a community atmosphere that reflects Miami’s sailing heritage.

The J/70 Midwinters Championship brings together highly-skilled teams in the fast-paced J/70 keelboat class. Hosted at Shake-A-Leg Miami, the event offers five to seven races in varying conditions and showcases the depth of the one-design fleet.

Closing out the winter series, the fourth leg of the M32 Miami Winter Series is where champions are crowned, strategies are refined and the season’s narrative culminates. With Biscayne Bay offering its picturesque but challenging waters, it’s a finale event not to be missed.