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Sail
The SAIL section of ALL AT SEA covers sailing racing, regattas, and the people and programs driving competitive sailing across the Caribbean and Southeast United States. From iconic events like Antigua Sailing Week and the St. Maarten Heineken Regatta to grassroots youth…
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What’s on — Regattas & races
Oct11
PCYC Fall Series Dinghy Racing NowPetite Calivigny Yacht Club, Le Phare Bleu, Grenada
Oct30
Salty Dawg Rally to the Caribbean NowBluewater Yachting Center
Oct31
Discover the Caribbean Regatta, Ponce Yacht and Fishing Club NowPonce Yacht & Fishing Club, Puerto Rico
Nov1
Route du Rhum – Destination Guadeloupe NowSaint-Malo, France to Pointe-à-Pitre, Guadeloupe
Nov4
ISCA Sunfish World ChampionshipThe Hotel on the Cay, Protestant Cay
Nov7
Willy T Race & Virgin’s CupTortola to the Willy T, The Bight, Norman Island, BVI
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More Sail
- St. Thomas, USVISt. Thomas to Host the Clipper Round the World Race in 2027-28 — and Field a USVI Team October 23, 2026
- St. Maarten / St. MartinSailability Returns to St. Maarten Yacht Club for the 2026–2027 Season October 22, 2026
- St. Thomas, USVINew USVI Sailing Week Debuts April 8-11, 2027 – Race, Rally & Shop the Expo! October 6, 2026
- GuadeloupeAlexia Barrier Chases Another First at the Route du Rhum September 23, 2026
- AntiguaDoes the CSA Majors Trophy Redefine the Caribbean Racing Season? August 29, 2026
- CaribbeanHelp Tracy Schmitt Reach the World Sailing Inclusion Championships August 25, 2026
- CaribbeanRS Aira 22 Expands Family Sailing in the Caribbean April 19, 2026
- St. Thomas, USVIPrivateer, Cachondo, ISCA, and Boogie Board Bandits Lead Their Classes after Day 2 @ 52nd St. Thomas International Regatta April 5, 2026
- St. Thomas, USVISt. Thomas International Regatta 2026 Opens with Perfect Caribbean Sailing Conditions April 5, 2026
- St. Thomas, USVIRoundabout, Black Pearl & Peacemaker Podium Finishers @ Round the Rocks Race – Nearly 40 Boats Set Sail in 52nd St. Thomas International Regatta Starting Friday April 3, 2026
- St. Thomas, USVIHappening This Week! 10th Round the Rocks Race, April 2, 2026 52nd St. Thomas International Regatta, April 3-5, 2026 March 30, 2026
- St. Thomas, USVISt. Thomas International Regatta 2026 Set for April 2–5 with IC24 Championship and Caribbean Trade Wind Racing March 11, 2026
- The Long Way Round: Why Caribbean Distance Racing Is Back February 28, 2026
- St. Thomas, USVISail Hard, Play Hard – A Perfect Balance at the Second Annual Women’s Regatta Camp, St. Thomas Sailing Center, U.S. Virgin Islands February 19, 2026
- AnguillaInside Anguilla’s Fierce and Beautiful Tradition of Boat Racing January 27, 2026
- St. Croix, USVIThree Sheets Regatta – An Epic Sailing Adventure @ 3 Days – February 19-22, 2026 – 3 U.S. Virgin Islands January 27, 2026
- St. Thomas, USVISecond Annual Women’s Regatta Camp, January 26-31, 2026 St. Thomas, U.S. Virgin Islands Still Time to Enter! January 27, 2026
- Antigua2026 Antigua Bermuda Race Returns, Draws Fleet to SailGP Bermuda December 2, 2025
- AntiguaTriple the Sailing Fun for 2026! December 2, 2025
- BequiaSVG Sailing Week Sets Course for Growth in 2026 with More Racing, Regional Youth, and Island Fun November 17, 2025