CARIBBEAN SAILING REGATTAS 2026
From the turquoise waters of Barbados to the trade-wind shores of Antigua, the 2026 Caribbean sailing season is packed with world-class regattas that bring crews together for thrilling competition and unforgettable island experiences.
Barbados Sailing Week
Barbados Sailing Week
Barbados Sailing Week
January 15–22, 2026
Barbados Sailing Week kicks off the 2026 Caribbean sailing season with thrilling coastal and inshore yacht racing, including the iconic Mount Gay Round Barbados Race. This premier Caribbean sailing regatta attracts competitive fleets from across the region while combining exciting races with vibrant shore-side events. It’s perfect for performance crews, families, and youth sailors looking to experience top-level yacht racing.
Grenada Sailing Week
Barbados Sailing Week
Barbados Sailing Week
January 25–30, 2026
Grenada Sailing Week is an early-season Caribbean sailing regatta featuring coastal races and short offshore legs. Attracting local and international yachts, the event offers challenging competition while showcasing Grenada’s vibrant sailing culture. It’s a must-do regatta for crews preparing for the wider Caribbean racing season.
RORC Caribbean 600
Barbados Sailing Week
RORC Caribbean 600
February 23, 2026
The RORC Caribbean 600 is a premier offshore Caribbean yacht racing event covering 600 nautical miles around 11 islands. Starting and finishing in Antigua, this challenging regatta attracts high-performance yachts from around the world and tests navigation, seamanship, and endurance. It is one of the most prestigious and demanding events on the 2026 Caribbean sailing calendar.
St. Maarten Heineken Regatta
St. Thomas International Regatta (STIR)
BVI Spring Regatta & Sailing Festival
March 5–8, 2026
The 2026 St. Maarten Heineken Regatta is a world-class Caribbean sailing event featuring four days of competitive yacht racing in consistent trade winds. International fleets gather for coastal and inshore races, while onshore festivities, live music, and parties make it one of the most social regattas in the Caribbean. This regatta is a must-attend for sailors seeking both performance racing and a festive atmosphere.
BVI Spring Regatta & Sailing Festival
St. Thomas International Regatta (STIR)
BVI Spring Regatta & Sailing Festival
March 23–29, 2026
The BVI Spring Regatta combines competitive yacht racing, including the famous Round Tortola, with a full programme of island festivals and social events. Crews and charter sailors enjoy a mix of coastal and inshore racing while experiencing one of the Caribbean’s most celebrated sailing festivals. This 2026 event is ideal for both serious racers and social sailing enthusiasts.
St. Thomas International Regatta (STIR)
St. Thomas International Regatta (STIR)
St. Thomas International Regatta (STIR)
April 3–5, 2026
The St. Thomas International Regatta is a premier Caribbean sailing event held over Easter Weekend, attracting competitive fleets across multiple classes. Races include windward/leeward and island courses, while participants enjoy the lively island atmosphere, live music, and beachside events. STIR combines high-level yacht racing with the vibrant culture and hospitality of the U.S. Virgin Islands, making it a highlight of the 2026 Caribbean sailing season.
Antigua Racing Cup
Antigua Sailing Week
Antigua Sailing Week
April 9–12, 2026
The Antigua Racing Cup is an event for racing purists—those who prefer high-energy, coastal racing with a fast-paced schedule and a focus on spirited competition. The event will feature 4 days of exhilarating races in conditions envied by most – balmy temperatures, trade winds, big seas at very short distances from shore.
Antigua Sailing Week
Antigua Sailing Week
Antigua Sailing Week
April 25–May 1, 2026
The Antigua Racing Cup is a high-intensity Caribbean yacht racing event, ideal for crews looking to fine-tune tactics ahead of Antigua Sailing Week. Featuring challenging coastal courses and steady trade winds, this regatta attracts competitive international and local fleets, offering one of the region’s most tactical sailing experiences.
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