Prepare your sailing calendar for this season’s unforgettable Caribbean sailing regattas 25/26
Hoist the sails, thrill-seekers! The Caribbean, where sparkling seas meet perfect breezes, the stage is set for one of the world’s most exciting regatta seasons. Imagine heart-pounding races framed by lush islands, powdery sands and that irresistible tropical spirit.
Each regatta blends fierce competition with laid-back island charm, giving sailors and spectators alike an experience that’s equal parts adrenaline and pure paradise.
And when the sun sets? The legendary beach parties, steel drum beats and rum fuelled celebrations keep the vibe alive long after the last finish line. With the 2025/26 calendar packed with can’t-miss events, the invitation is clear. Whether you’re a veteran racer or a dreamer ready to explore by sea, now’s your moment. Book a yacht, gather your crew, feel the trade winds and let the Caribbean regatta season sweep you into memories you’ll treasure forever.
October 2025
ST. BARTHS BUCKET REGATTA SAINT BARTHÉLEMY
Usually mid-October. One of the most prestigious superyacht regattas worldwide, featuring a stunning fleet of large sailing yachts.
TORTOLA SAILING FESTIVAL BRITISH VIRGIN ISLANDS
Late October. A premier sailing event attracting both racing and cruising yachts, with a mix of local and international competitors.
January 2026
LES VOILES DE SAINT BARTH (WINTER SERIES)
Some winter sailing events and racing series continue into January, featuring competitive superyacht racing.
CARIBBEAN SAILING ASSOCIATION WINTER REGATTA CIRCUIT
Various islands host winter series events through January, February and March, including superyacht classes.
February 2026
ANTIGUA CLASSIC YACHT REGATTA ANTIGUA
Mid-February. Focuses on classic and vintage yachts, often running alongside other sailing events.
BVI SPRING REGATTA & SAILING FESTIVAL BRITISH VIRGIN ISLANDS
Late February. A major sailing event attracting international racers and superyachts.
March 2026
RORC CARIBBEAN 600 YACHT RACE STARTS AND FINISHES IN ANTIGUA
Usually mid-March. A 600-mile race around multiple Caribbean islands, attracting some of the world’s best racing yachts and superyachts.
ST. MAARTEN HEINEKEN REGATTA MARCH RACES
Some extended races or related sailing events may occur in early March.
April 2026
ANTIGUA SAILING WEEK ANTIGUA
Mid-April. The Caribbean’s premier regatta for cruisers and racers, featuring competitive superyacht classes and spectacular social events.
