A sandy beach with palm trees and houses in the background

Explore Sailing Voyages in Anguilla 🇦🇮

Cover photo by @sradams57 on Unsplash

Voyage photo from Race from Sint Maarten to Anguilla and back

Tom Chaleki & 1 other

12 July 2026 at 11:33

Day 4 Friar Bay St. Martin

Gypsy Soul

25 knot winds First leg downwind - sailed with full jib Seconds leg upwind - very rolly I decided to motor

14.3NM

4h 1m

Sandy Ground Village, Anguilla to Friar’s Bay, Saint Martin

Tom Chaleki & 1 other

10 July 2026 at 09:58

Day 2 Road Bay Anguilla

Gypsy Soul

16.8NM

4h 4m

Grand-Case, Saint Martin to Sandy Ground Village, Anguilla

Kevin Radosevich

3 July 2026 at 10:15

Anguilla charter

42.5NM

4h 4m

Sandy Ground, Saint Martin

Kevin Radosevich

8 July 2026 at 09:55

Anguilla charter

37.6NM

6h 15m

Sandy Ground, Saint Martin

Nataliia Haakansson & 1 other

19 June 2026 at 11:02

Window Trip

Neptuno

We had the Emergency escape window fall off the boat. Then we started taking on water, as it washed in. We went to the beach and anchored. When you were able to get all of the water pumped out and put a patch over the window.

18.7NM

4h 11m

Prickly Pear Cays, Anguilla to Simson Bay Village, Sint Maarten

Dickie Grace, Shadrach St.Croix & 1 other

10 June 2026 at 17:23

kelea

106.6NM

16h 39m

Benner, U.S. Virgin Islands to Koolbaai, Sint Maarten

Gordon & Nataliia Haakansson

16 June 2026 at 13:19

Neptuno

19.3NM

3h 25m

Baie Blanche, Saint Martin to Sandy Ground Village, Anguilla

Gerhardus Botha

14 March 2026 at 09:43

Race from Sint Maarten to Anguilla and back

VanCat?

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.