The Anguilla Youth Sailing Club (AYSC) has plenty to smile for. After three years of dreaming, fundraising, and rallying support from across the island, the club finally welcomed its sparkling new fleet of six sailing boats, shipped in from England earlier in September.
The boats, which together cost a hefty US$72,000, mark the successful end of a long campaign that saw contributions trickle in from local businesses, well-wishers, and generous individuals. Republic Bank, Straw Hat, Tipsy Turtle, Brigid Arcand, and several other individual contributors all pitched in to help turn the sails of ambition into reality.
On Saturday 27th September 2025, the new fleet was officially christened, with eager students setting out from Sandy Ground in three of the vessels for their maiden voyage. Perfect skies and calm waters made it a day to remember, particularly since the day before had been plagued by inclement weather.
The excitement was written on every face, but none more so than board member Cheryl Webster’s.
“I’m just so happy,” Webster exclaimed, still buzzing from the milestone. “And it’s crazy to look back on now because three years ago all we had was a flyer asking people for money with a picture of the boat. So, actually seeing the boats here is absolutely surreal.”
For Webster, the moment is more than just about new equipment; it’s about the doors sailing can open. She proudly shared that one of the club’s students had just been accepted into a prestigious maritime academy. “There’s a lot of paths to take through sailing. And it’s our national sport too, after all. So, we’re keeping the culture alive.”
With a grin, she also reminisced on when the fleet first touched Anguillian shores. Immediately, she exclaimed, “We did it, Joe!” to head instructor, Kendal Richardson — referencing former US Vice President Kamala Harris’s viral 2020 call to President Joe Biden when they won the election.
Kendal Richardson was equally moved. After accompanying the students on their first loop around the bay, he returned to shore visibly emotional. The near-tears were not just about the moment but the years of effort and hope poured into bringing this project to life.
The young sailors themselves were thrilled, though one admitted it took a little while to get the hang of handling the fresh sails. By the end of the session, however, they were gliding smoothly across Sandy Ground’s glittering waters.
Meanwhile, Webster, Richardson, and three other members of the AYSC departed on Thursday 2nd October for Italy, where they’ll join the 57th edition of Barcolana in Trieste. The week-long festival, which will be held from October 3rd to 12th, culminates in the world’s largest regatta — a dazzling event that will no doubt add another layer of inspiration for Anguilla’s budding sailors.
For now, though, AYSC’s new fleet stands as a symbol of perseverance, community spirit, and Anguilla’s unshakable connection to the sea. The club has extended heartfelt thanks to every individual and business who contributed to this milestone.
By Janissa Fleming
