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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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The Sail desk
What’s on — Regattas & races
Oct2
Barcolana NowGulf of Trieste
Oct10
Virgin Islands-Puerto Rico Friendship Regatta NowSt. Thomas Yacht Club, USVI
Oct11
Bonaire Regatta NowBonaire
Oct11
PCYC Fall Series Dinghy Racing NowPetite Calivigny Yacht Club, Le Phare Bleu, Grenada
Oct17
Regata HispanidadSanto Domingo Yacht Club, Boca Chica, Dominican Republic
Oct23
Caribbean Dinghy ChampionshipSt. Maarten Yacht Club
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More Sail
- 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
- CaribbeanCSA to Offer Dual CSA–IRC Scoring Across 2026 Caribbean Regatta Circuit November 17, 2025
- BequiaBequia’s Double-Ender Legacy: Preserving Boatbuilding Heritage at the Bequia Heritage Museum October 23, 2025