Explore Sailing Voyages in Sint Maarten 🇸🇽
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Simson Bay Village to Koolbaai, Sint Maarten
Charlotte H & 1 other
1 June 2026 at 03:56
Woke at 3:30am and set off in very light winds from E. They remained light, which was very frustrating, though the advertised light swell was a blessing. Unfortunately it meant we motor sailed basically the whole way to ensure we got in before dark, first with and mainsail out beyond Dog Island, Anguilla, before jibing round and heading toward North Sound with the genoa. By 8:00am we were out of sight of land, which remained the case amid thick Sahara dust until about 4:00pm. About 9:30am I spotted a tall ship under full sail and slowed to allow them to close - quite a sight!

Koolbaai, Sint Maarten to North Sound Settlement, British Virgin Islands

Koolbaai, Sint Maarten to Horta, Portugal
Wayne Busch - Well done so far.
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Jolly Harbour, Antigua and Barbuda to Philipsburg, Sint Maarten
Excellent wind, won the race the Anguilla and had lunch in the Bay in front of the hotel, with turquoise water and beautiful white beaches. Very contested race back with Philippe on the way back. Capsized 2 boats. After that no gennaker was allowed. Lost the race because we went too far offshore. His strong point is downwind sailing and we matched him for a few miles.
3

Koolbaai, Sint Maarten
Scott Salka, Kevin Donahoe & 1 other
2 May 2026 at 10:17
18

Koolbaai, Sint Maarten to Halesite, United States

Philipsburg, Sint Maarten to Jolly Harbour, Antigua and Barbuda
Jeff Miller, Steve & 1 other
2 May 2026 at 10:06
4

Koolbaai, Sint Maarten to Saint George, Bermuda







































