What’s on
Caribbean Regattas 2027
Every regatta we track, from the Willy T and the Round Tortola in November to Antigua Sailing Week in April — in date order, with who fixed each date. Confirmed: the organiser or the Caribbean Sailing Association has published it. Provisional: the usual weekend, until the organiser posts.
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49 Caribbean regattas · 40 confirmed by the organiser · 9 provisional · last change recorded November 12, 2026
| Dates | Regatta | Where | Date set by |
|---|---|---|---|
| November 2026 | |||
| Nov 4 – Nov 14 | ISCA Sunfish World Championship Now | US Virgin Islands | Confirmed |
| Nov 14 | Club Racing, Royal BVI Yacht Club | British Virgin Islands | Confirmed |
| Nov 14 – Nov 15 | Mini Dinghy Regatta, Antigua Yacht Club | Antigua and Barbuda | Confirmed |
| Nov 14 – Nov 15 | Discover the Caribbean Dinghy Regatta | Puerto Rico | Confirmed |
| Nov 16 – Nov 23 | The St. Barth Cata Cup | French West Indies | Confirmed |
| Nov 20 – Nov 22 | Jolly Harbour Yacht Club (JHYC) Annual Regatta | Antigua and Barbuda | Confirmed |
| Nov 21 | RBVIYC – Nanny Cay Round Tortola Race | British Virgin Islands | Confirmed |
| Nov 26 – Nov 29 | Sol Sint Maarten Optimist Championship | St. Maarten / St. Martin | Confirmed |
| Nov 27 – Nov 29 | Mango Bowl Regatta | St. Lucia | Confirmed |
| Nov 28 | Coral Bay Yacht Club Annual Thanksgiving Regatta | US Virgin Islands | Confirmed |
| December 2026 | |||
| Dec 3 – Dec 6 | Course de L’Alliance | St. Maarten / St. Martin | Confirmed |
| Dec 5 | Gustav Wilmerding Regatta | British Virgin Islands | Confirmed |
| Dec 10 – Dec 20 | McIntyre 580 Transat | Antigua and Barbuda | Provisional |
| Dec 12 | Christmas Hamper Race | Trinidad and Tobago | Confirmed |
| Dec 12 | The World’s Toughest Row | Antigua and Barbuda | Provisional |
| Dec 18 – Dec 20 | Hightide Regatta, Antigua Yacht Club | Antigua and Barbuda | Confirmed |
| Dec 19 | Golden Hind Chandlery Commodore’s Race | British Virgin Islands | Confirmed |
| Dec 26 | Boxing Day Barrel, Antigua Yacht Club | Antigua and Barbuda | Provisional |
| Dec 31 | Nelson’s Pursuit Race, Antigua Yacht Club | Antigua and Barbuda | Confirmed |
| January 2027 | |||
| Jan 10 | RORC Transatlantic Race | Grenada | Confirmed |
| Jan 16 – Jan 21 | Barbados Sailing Week | Barbados | Confirmed |
| Jan 16 – Jan 17 | Antigua Yacht Club One Design Small Keelboat Regatta | Antigua and Barbuda | Provisional |
| Jan 23 | Sandy Island Race, Antigua Yacht Club | Antigua and Barbuda | Provisional |
| Jan 24 | NSA Dinghy Dash | Antigua and Barbuda | Provisional |
| Jan 27 – Jan 31 | 44Cup Antigua | Antigua and Barbuda | Provisional |
| Jan 31 – Feb 5 | Grenada Sailing Week | Grenada | Confirmed |
| February 2027 | |||
| Feb 3 – Feb 7 | Caribbean Multihull Challenge | St. Maarten / St. Martin | Confirmed |
| Feb 9 – Feb 12 | One Design Elite Caribbean Championship, Jolly Harbour Yacht Club | Antigua and Barbuda | Provisional |
| Feb 12 – Feb 14 | Jolly Harbour Valentine’s Regatta | Antigua and Barbuda | Confirmed |
| Feb 13 – Feb 14 | Grenada Workboat Regatta | Grenada | Confirmed |
| Feb 16 – Feb 19 | RORC Nelson’s Cup Series | Antigua and Barbuda | Confirmed |
| Feb 20 | Bocas Del Toro Regatta | Panama | Confirmed |
| Feb 22 – Feb 26 | RORC Caribbean 600 | Antigua and Barbuda | Confirmed |
| March 2027 | |||
| Mar 4 – Mar 7 | St. Maarten Heineken Regatta | St. Maarten / St. Martin | Confirmed |
| Mar 10 – Mar 14 | The Superyacht Challenge | Antigua and Barbuda | Confirmed |
| Mar 17 – Mar 21 | Antigua Racing Cup | Antigua and Barbuda | Confirmed |
| Mar 17 – Mar 21 | St Barths Bucket Regatta | French West Indies | Confirmed |
| Mar 21 – Mar 29 | SVG Sailing Week | St. Vincent & The Grenadines | Confirmed |
| Mar 21 – Mar 27 | PAYS Dominica Yachting Festival & Race to Mero | Dominica | Confirmed |
| Mar 29 – Apr 4 | BVI Spring Regatta and Sailing Festival | British Virgin Islands | Confirmed |
| April 2027 | |||
| Apr 4 – Apr 9 | Oyster Regatta | Antigua and Barbuda | Confirmed |
| Apr 8 – Apr 11 | STIR – St. Thomas International Regatta | US Virgin Islands | Confirmed |
| Apr 9 – Apr 11 | Budget Marine ILCA & Optimist Open | Antigua and Barbuda | Provisional |
| Apr 14 – Apr 19 | Antigua Classic Yacht Regatta | Antigua and Barbuda | Confirmed |
| Apr 21 – Apr 25 | Antigua Sailing Week | Antigua and Barbuda | Confirmed |
| May 2027 | |||
| May 28 – May 30 | Vuelta a Culebra Regatta | Puerto Rico | Confirmed |
| May 28 – May 30 | Aruba International Regatta | ABC Islands | Confirmed |
| June 2027 | |||
| Jun 5 | Lowell Wheatley Anegada Pursuit Race | British Virgin Islands | Confirmed |
| September 2027 | |||
| Sep 18 | Back to School Regatta & ILCA Masters Championships | British Virgin Islands | Confirmed |
What moved
- The Superyacht Challenge 2027 — dates moved Sep 17
- Barbados Sailing Week 2027 — dates moved Aug 28
- Caribbean Multihull Challenge 2027 — dates moved Aug 28
- Antigua Sailing Week 2031 — dates moved Aug 28
Is your event missing?
Regattas, races, rallies, tournaments, festivals — if it happens on the water and it isn’t here, tell us and our events desk will add it to the calendar.
Add your event → or see the whole season →
Dates wrong on an event we already list? Every event page has an Update us link that reaches the same desk.
