Competitors in this year’s Anguilla Regatta were treated to ideal racing conditions, with strong tradewinds delivering two exciting days of competition along with plenty of shoreside hospitality in Road Bay.
Co-hosted by the Sint Maarten Yacht Club (SMYC) and the Anguilla Sailing Association, racing got underway on Saturday, May 23, from Simpson Bay with three CSA entries on the start line. A brisk easterly breeze in the upper teens, gusting into the mid-20s, made for a fast and spirited crossing to Anguilla.
After a short upwind leg, the fleet turned northwest and charged toward the western corner of St. Maarten, with colorful spinnakers appearing on the horizon. Following a lively crossing of the Anguilla Channel, competitors settled into upwind sailing along Anguilla’s north coast, where gusts rolling off the island kept crews on their toes.
The finish in Road Bay was tight. When corrected times were tallied, the Beneteau 47 Dauntless secured third place, J/105 More Zessin’ took second, and the Melges 24 Team Island Water World claimed the top spot.
Once ashore, the focus shifted from racing to celebration. The Anguilla Sailing Association once again proved itself a gracious host, welcoming crews with drinks on Sandy Ground beach after customs clearance, followed by dinner and a lively beach party complete with DJ entertainment.
Sunday morning began with breakfast for competitors before the fleet returned to the water for one final race in Road Bay. The breeze remained strong, and racing along Anguilla’s spectacular coastline stayed competitive to the finish.
With cumulative scores counted, Dauntless finished third overall, More Zessin’ secured second, and Team Island Water World stood atop the podium as overall winner of the 2026 Anguilla Regatta.
“We had an amazing regatta combined with a great party,” said race officer Lars Ouwens. “A special thanks to the Anguilla Sailing Association team for all their hard work. I would encourage even more sailors to join next year’s Anguilla Regatta.”
Organizers also thanked the competitors, volunteers, and race committee whose efforts helped make the event possible, while already looking ahead to an even bigger regatta in 2027.
Final Results
1st Place: Team Island Water World
2nd Place: More Zessin’
3rd Place: Dauntless
Established in 1980, the Sint Maarten Yacht Club promotes watersports and sailing throughout St. Maarten and organizes several major events annually, including the St. Maarten Heineken Regatta. Through its youth sailing program, the club also introduces young sailors to the sport while teaching teamwork, perseverance, and confidence.
