The Caribbean Sailing Season 2026 - Regatta Calendar
Barbados Sailing Week 2026 marks the beginning of the Caribbean racing season. Here’s an overview of the other exciting regattas in the Caribbean for 2026.
Barbados Sailing Week
Dates: January 15 – 21, 2026
Description: Get inspired by the island of Barbados. This regatta features three coastal races at the home of Mount Gay and the signature Mount Gay Round Barbados Race and ends with the Rum to Spice Regatta connecting to Grenada Sailing Week.
https://www.roundbarbados.com/
Grenada Sailing Week
Dates: January 25 – 30, 2026
Description: This regatta features five days of competitive racing around the islands of Grenada and Cariacou, complemented by vibrant evening parties and a lay day for relaxation.
https://grenadasailingweek.com/
Caribbean Multihull Challenge Race & Rally
Dates: January 29 – February 1, 2026
Description: The only regatta in the Caribbean dedicated exclusively to multihull racing, featuring thrilling competition for catamarans and trimarans of all sizes and hosted in St. Maarten/St. Martin, this event blends high-speed racing with a relaxed rally atmosphere.
caribbeanmultihullchallenge.com
RORC Caribbean 600
Dates: February 23 - 27, 2026
Description: A challenging 600-nautical-mile offshore race starting and ending in Antigua, navigating around 11 Caribbean islands.
https://www.caribbean600.rorc.org/
St. Maarten Heineken Regatta
Dates: March 6 – 8, 2026
Description: Combining world-class racing with lively parties, this regatta attracts sailors from over 35 countries.
https://www.heinekenregatta.com/
Superyacht Challenge Antigua
Dates: March 6 – 10, 2026
Description: An exclusive event for superyachts, offering competitive racing and social events in the historic Nelson's Dockyard.
https://superyachtchallengeantigua.com/
St. Barths Bucket Regatta
Dates: March 13 – 16, 2026
Description: An invitation-only regatta featuring some of the world's most impressive superyachts competing in the picturesque waters of St. Barths.
https://bucketregatta.com/
St. Thomas International Regatta (STIR)
Dates: March 27 – 29, 2026
Description: Renowned as the 'Crown Jewel of Caribbean Yacht Racing,' STIR offers competitive racing and warm island hospitality.
https://stthomasinternationalregatta.com/
BVI Spring Regatta & Sailing Festival
Dates: March 30 – April 5, 2026
Description: A week-long event featuring a sailing festival followed by three days of intense racing in the British Virgin Islands' pristine waters.
https://bvispringregatta.org/
St. Vincent and the Grenadines Sailing Week
Dates: April 12th – 15th, 2026
Description: This event offers an unforgettable adventure celebrating the sea, the thrill of sailing, and vibrant island culture, paired with scenic beauty.
https://svgsailingweek.com/
Les Voiles de St. Barth Richard Mille (Not confirmed)
Dates: April 12 – 18, 2026
Description: A prestigious regatta offering competitive racing for various classes, set against the stunning backdrop of St. Barthélemy.
https://lesvoilesdestbarth.com/
Antigua Sailing Week
Dates: April 25 – May 1, 2026
Description: One of the Caribbean's premier sailing events, attracting a large fleet for competitive racing and vibrant shoreside festivities.
https://sailingweek.com/