Five talented sailors from Anguilla recently represented the island with remarkable success in a series of prestigious regattas in Italy, as part of the Night Shadow Sailing Syndicate. Thanks to a collaborative partnership between the Anguillian government and the South West Harbour Group—the developers behind the Port Nimara Marina at Altamer—the sailors not only competed but excelled, securing podium finishes in every race they entered.
Among their achievements was a standout performance at the Barcolana Regatta, the world’s largest regatta, where they placed 22nd overall out of 1,757 boats and 3rd in their category. These stellar results underscore the potential of Anguillian sailors to compete at the highest level on a global stage.
Cheryl Webster, a board member of the Anguilla Youth Sailing Club, described the experience as nothing short of transformative. “It was chaos—organised chaos,” she said, recalling the breathtaking view of thousands of sails blotting out the horizon. “You couldn’t see the mountains or even the sea—just sails. It was truly spectacular.”
For Kendal Richardson, head instructor at the Youth Sailing Club, the sheer scale of the event and the diversity of boats were inspiring. “There were high-tech racing boats alongside tiny dinghies barely 10 feet long. Seeing that love for the sport, across all levels and ages, was amazing,” he shared.
The Anguillian team competed in four regattas, including events in Trieste and the Bay of Venice, working alongside seasoned sailors such as Olympic champions and an Italian national sailing champion who served as their tactician. Webster highlighted the immense learning opportunity this provided: “Having an Olympic sailor guide us was incredible. It was tough but rewarding, and we performed extremely well.”
The journey wasn’t without its challenges. Adjusting to a new boat—the TP52, part of a high-performance one-design class—required the team to quickly adapt. “Every boat has its quirks, and it takes time to get comfortable,” Richardson explained. Meanwhile, Webster faced language barriers as Italian and German often dominated conversations during hectic moments on the water.
Yet, these obstacles only strengthened the team’s resolve. Dedication to practice and a strong sense of camaraderie helped them overcome hurdles. “We formed such a close bond,” Webster said. “We wanted to succeed not just for ourselves but for each other.”
The Anguilla Youth Sailing Club has been instrumental in nurturing local talent since its founding in 2006. Operating as a non-profit organisation, the club has introduced over 1,000 students to the national sport, with 70% of them receiving free training. “We’ve always aimed to provide opportunities for Anguillian youth,” said Webster.
Their involvement in the Night Shadow Sailing Syndicate began through a serendipitous connection facilitated by the Hon. Premier Dr. Ellis. L Webster. The Swiss-led South West Harbour Group, with its commitment to corporate social governance, saw the potential in introducing Anguillian sailors to international competitions.
The success in Italy has sparked dreams of more robust opportunities for Anguilla’s sailors. “This achievement highlights the need for a national sailing programme,” Webster noted. “Many Caribbean islands have one, and sailing isn’t even their national sport. It’s time Anguilla invests in its future sailors.”
The sailors returned home with not just medals but invaluable experiences and a renewed passion for their craft. “It was unforgettable,” said Richardson. “The exposure was eye-opening, and the support from the Anguillian and international communities made it all possible.”
On behalf of the Youth Sailing Club, Richardson and Webster both expressed their gratitude to the Government of Anguilla, Port Nimara at Altamer, Southwest Harbor Group, Calypso, and the Anguilla Tourist Board for their support in helping them reach their goals and achieve their accomplishments.
