Regatta

The St. Maarten Heineken Regatta will celebrate its 46th edition in 2026 from MARCH 5-8, 2026. It is the largest regatta in the Caribbean and likely the largest warm water regatta in the world.

The St. Thomas International Regatta (STIR) is taking a tack towards tradition by moving the event’s date to Easter Weekend, April 3-5, 2026. This global holiday, a calendar staple for the International Rolex Regatta and now STIR for over two decades, marks an occasion when families and friends make time to gather and celebrate.

Regularly attracting over a thousand of the greatest sailors from across the globe, the Les Voiles De Saint Barth is a fantastic regatta for charter guests to join in on.

Regattas in The Abacos is brought to life by a dedicated team of passionate volunteers who share a love for sailing and a deep commitment to showcasing the beauty of the Abacos, Bahamas. This enthusiastic group works tirelessly to organize every aspect of the event, from planning the races to coordinating the vibrant evening celebrations.

Their goal is not only to create an unforgettable experience for participants and spectators but also to highlight the stunning waters, rich culture, and warm hospitality that make the Abacos so special. Their efforts ensure the regatta remains a cherished tradition for the sailing community and a proud celebration of this island paradise.

Weekend regatta linking the sailing communities of the USVI and Puerto Rico, hosted by St. Thomas Yacht Club.

Two days of keelboat and dinghy racing off Boca Chica to mark Hispanic Heritage Day.

The airline-industry regatta sails a relaxed racing itinerary around the British Virgin Islands.

The Caribbean Sailing Association's dinghy championship, hosted in Sint Maarten.

Ponce Yacht & Fishing Club's regatta on the south coast, with keelboat and dinghy classes racing in the Caribbean Sea.

The Sunfish class world championship comes to St. Croix.

The international F18 catamaran regatta raced off Saint-Jean beach.