With just 20 days to go, anticipation is building for the 56th edition of Antigua Sailing Week (ASW), one of the most prestigious regattas in the Caribbean and a cornerstone of the global sailing calendar. Set to unfurl its sails on April 26, 2025, this year’s event promises another stellar lineup, blending high-octane racing with Antigua’s signature blend of hospitality, tropical charm and vibrant shoreside festivities.
From world-class racers to passionate cruisers, Antigua Sailing Week continues to offer something for everyone. More than just a competition, the regatta is a magnet for international and local sailors, seasoned professionals, long-term cruisers and bareboat charterers alike. Participants will race across a broad spectrum of monohull and multihull classes, drawn by challenging courses and the island’s legendary allure.
Among this year’s headline competitors is Roy Disney, carrying forward a family tradition aboard the formidable Pyewacket70, a Volvo 70 that has competed across Europe and the U.S. East Coast. The late Roy E. Disney, Roy’s father, won the Lord Nelson Trophy at ASW in 2002 aboard an earlier Pyewacket and his legacy lives on in the latest generation’s competitive spirit. Having already raced the Caribbean 600, Roy Disney and his international crew will remain in Antigua to contend for top honors at ASW.
Joining him on the high-performance end of the fleet is Philip Rann, trading in his Swan 80 for the turbo-charged VOR 65 Sailing Poland. At 79 feet, Lennart Davidsson’s Kialoa III currently holds the title for the largest entry this year. All three boats, along with other performance vessels, will tackle newly extended courses which is designed specifically for high-speed thrills and strategic challenges.
“We created these 20 to 50 mile courses to allow high-performance boats to stretch their legs with fast reaching angles, as well as tactically engaging upwind and downwind legs,” said Race Manager Jaime Torres.
Multihull entries are also making waves this season, with a growing fleet and new competition formats. Adrian Lee, formerly a monohull sailor, has made the leap to a powerful HH66 catamaran Lee Overlay Partners 3. Lee praised both the island’s sailing conditions and ASW’s course innovation, describing the switch to multihull racing as “like moving from a propeller plane to a jet.”
Another standout in the multihull division is Guy Chester aboard his Crowther 46 trimaran Ocean’s Tribute. Chester, last year’s multihull class champion, is in the hunt for the inaugural Windies Multihull Trophy, a new regional series that includes ASW and the Peters & May Round Antigua Race as its final legs. “We’re flat out trying to win,” said Chester, though he acknowledged that rivals from Barbados and Grenada currently lead the standings.
While the high-tech giants capture attention, the heart of Antigua Sailing Week remains in its CSA-rated mid-size monohull fleet. Leading the charge is El Ocaso, the chartered J/122 that has become a dominant force in recent editions. A win this year would secure its place in ASW history as a three-time champion aboard the same class, a feat matched only by legends like Larry Ellison’s Sayonara and Sir Peter Harrison’s Sojana.
Racing this year under Steve Rigby, El Ocaso will face stiff competition, including the formidable local racer Jim Voss’s RP37 Warthog, fresh from a major refit and a win at the RORC Nelson’s Cup in February. With such evenly matched talent on the start line, the contest for the Lord Nelson Trophy promises to be one of the most thrilling in years.
For racers seeking close-quarters action, the Petticrow Dragons and RS Elite fleets offer tightly structured one-design formats with up to 15 races over five days. Boats are available for charter directly from the Antigua Yacht Club marina, making it an ideal entry point for international sailors.
“You can fly in, get on a race-ready boat right at the epicenter of the action, and go rock this regatta,” said Torres. Courses will primarily be windward/leeward, with contingencies for racing inside Falmouth Harbor during extreme weather.
Meanwhile, the Club Class continues to provide an inclusive gateway for casual sailors and cruisers. With just one race per day and no spinnakers, the class uses a simplified self-declared rating system to keep the focus on fun and accessibility. “It’s about lowering barriers to entry while still offering solid racing and a great social atmosphere,” noted ASW President Alison Sly-Adams.
More Than Just Racing
Sly-Adams attributes ASW’s enduring success to more than world-class competition. “Antigua is a world-class destination and Sailing Week benefits from top-level race management,” she said. “But off the water, we have incredible venues to ensure every party is a lot of fun.”
The social calendar is as lively as the racecourse, drawing spirited participation from French island crews from Martinique, Guadeloupe, and St. Barts, as well as a strong contingent from Barbados. “They bring a contagious sail-hard, party-harder attitude,” she added.
With thrilling racing, inclusive classes and an unbeatable shoreside vibe, the 56th Antigua Sailing Week is poised to deliver another unforgettable chapter in the island’s storied maritime tradition. Whether you’re on a high-performance racer or a laid-back cruiser, one thing is certain: there’s no place quite like Antigua when the sails go up.
