Caribbean Sailing Events: From Antigua to St. Vincent and the Grenadines

February

Jolly Harbour Valentine’s Regatta – Antigua, 13-15 February

Held annually over Valentine’s weekend, the Jolly Harbour Yacht Club Valentine’s Regatta is a fun-filled celebration of sailing and community that welcomes everyone, from seasoned racers to first-time sailors.

RORC Nelson’s Cup Series – Antigua, 17-21 February

The RORC Nelson’s Cup Series is one of the Caribbean’s premier sailing events, offering the perfect mix of competitive racing and relaxed island hospitality. Organised by the Royal Ocean Racing Club (RORC) in association with the Antigua Yacht Club, the four-day regatta features a combination of tactical inshore and coastal courses, culminating in the thrilling Antigua 360° Race, a full circumnavigation of the island.

March

Antigua Superyacht Challenge – Antigua, 3-8 March

Every March, just before the St. Barths Bucket Regatta, Antigua hosts the Superyacht Challenge: a four-day showcase of thrilling, friendly racing for yachts over 80 feet. Run by the SYCA Committee under Paul Deeth, the regatta features daily 12–30 mile courses off Antigua’s south coast, with a Start/Finish line at iconic English Harbour.

St. Maarten Heineken Regatta – Sint Maarten, 5-8 March

The St. Maarten Heineken Regatta is one of the largest sailing event in the Caribbean and one of the biggest warm-water regattas in the world. Four days of world-class racing are paired with lively evenings in the Regatta Village, where participants enjoy local cuisine, ice-cold Heineken, and a vibrant mix of sport, business, and Caribbean energy.

St Barth Bucket Regatta – St. Barth, 12-15 March

The St. Barth Bucket Regatta, held every March, brings together the world’s top sailors to compete purely for the love of sailing. Known for its gentleman’s spirit, the event showcases stunning superyachts while giving back to the local community through its entry fees. Participation is by invitation, traditionally for yachts over 30 meters, though a special category now welcomes smaller yachts, letting more enthusiasts experience the magic of the Bucket.

P.A.Y.S. Dominica Yachting Festival – Dominica, 21-27 March

The PAYS Dominica Yachting Festival, launched in 2023, evolved from PAYS’ Yachtie Appreciation Week, an annual event started in 2016 to thank visiting yachts and promote Dominica’s new PAYS Mooring Field, sponsored by Offshore Passage Opportunities (OPO). The festival features parties, guided tours, and a range of fun activities for participants. 

April

SVG Sailing Week – Saint Vincent & The Grenadines, 29 March – 6 April

SVG Sailing Week is one of the Eastern Caribbean’s most exciting sailing events, combining world-class racing with the vibrant culture of Saint Vincent and the Grenadines. Participants enjoy thrilling races alongside lively parties, live music, and local cultural events at every stopover.

Antigua Classic Yacht Regatta – Antigua, 15-20 April

The Antigua Classic Yacht Regatta blends serious racing with laid-back island hospitality, plenty of rum, sunshine, and camaraderie, creating a truly unique experience. Onshore, participants enjoy lively events like open-mic music nights, adding to the festival atmosphere. 

Antigua Sailing Week -Antigua, 22-26 April

Yachts from around the world will gather in English and Falmouth Harbours for the 57th Antigua Sailing Week (ASW), one of the Caribbean’s premier regattas and a globally renowned sailing event. Returning to its roots, ASW will feature a shorter, four-day format from April 22–26, including the welcome party and racing around Antigua’s stunning waters, combining world-class competition with the event’s rich history and vibrant atmosphere.