The sails of Anguilla are once again billowing proudly across the Adriatic Sea, as Kendal “Kenny” Richardson and Cheryl Webster chart a new course for glory at the 57th edition of the Barcolana Regatta in Trieste, Italy. Representing the Anguilla Youth Sailing Club (AYSC), the duo, joined by three other team members, departed the island on Thursday, 2nd October 2025, to take part in what has become one of the most celebrated sailing festivals in the world.
From 3rd to 12th October, the port city of Trieste transforms into a maritime spectacle, hosting thousands of boats and tens of thousands of sailors and spectators for the Barcolana — the largest regatta in the world.
This year marks the second time Richardson and Webster have taken part in the Italian classic under the banner of Night Shadow 52, a Botin TP52 yacht led by a Swiss team. Their participation is made possible through a meaningful collaboration with the South West Harbour Group, developers of the Port Nimara Marina at Altamer, who have continued to support the AYSC’s global ventures.
Competing against some of the most formidable racing yachts in the world in the exclusive Barcolana Maxi — an invite-only class for vessels over 16 metres — the team aboard Night Shadow 52 began their campaign with an impressive third-place finish on corrected time after Day One.
As Webster explained in her update from Trieste on Thursday, 9th October, “The way corrected timing works is that boats vary in size. The only real requirement for the maxi is being over 16 metres — which we just about met — and a handicap formula ensures a level playing field for all competing yachts.”
Webster continued with her signature enthusiasm, offering a glimpse of the team’s anticipation for the days ahead: “Today, day two, we will be leaving Porto Piccolo Marina and we will be finishing at the Piazza in Trieste where the majority of the events for the Barcolana will take place. We’re very excited today. We’re hoping to give you some fantastic results.”
For Richardson and Webster, this competition is more than just a regatta — it’s a continuation of Anguilla’s growing legacy on the international sailing stage. Their performance last year was nothing short of remarkable: a first-place victory in their category at the 2024 Bernetti Cup, a podium finish at the Barcolana Maxi, 16th overall at the Barcolana itself, and a third-place class finish at the Veleziana Regatta in Venice.
Their return this year is a testament to both their personal dedication and the steady growth of Anguilla’s sailing community — one built on tradition, perseverance, and the boundless potential of island youth.
Later this month, the pair will be joined in Venice by fellow sailors Thomas Maccow, Samil Fleming, and Deja Carty to compete in the prestigious Venice Hospitality Challenge and the Regatta Veleziana — a fitting follow-up to the Barcolana, and another chance for Anguilla’s flag to fly high in European waters.
