One of the Caribbean’s most iconic sailing competitions, the 2026 edition of Antigua Sailing Week, delivered four days of unforgettable racing marked by wildly shifting conditions, razor-tight standings, and a reimagined fleet format that united competitive sailors and casual cruising enthusiasts from every corner of the globe. Held across a full circumnavigation of the tropical island, the event blended high-stakes on-water competition with lively shoreside celebrations, all anchored by Antigua’s world-famous natural coastal beauty.
Alison Sly-Adams, president of Antigua Sailing Week, explained that the event’s core mission centered on leveraging the island’s unique geography to deliver one-of-a-kind point-to-point courses, balanced by social gatherings that foster connection among participants. This year’s updated fleet structure successfully merged competitive racing fleets with a rally cruising division, creating an inclusive experience that catered to elite racers and leisure sailors alike.
The regatta kicked off from the historic starting point of English Harbour, heading toward Green Island on opening day. Moderate trade winds set a steady rhythm for the fleet, giving crews front-row seats to Antigua’s dramatic, turquoise-fringed coastline. After crossing the day’s finish line, sailors gathered for the laid-back Barefoot on the Beach event hosted by the Falmouth Ocean Club, setting the tone for the week’s signature blend of fierce competition and warm camaraderie.
Day two brought a sharp increase in difficulty, with shifting breeze and rolling North Swell that tested the tactical skills of both racing and cruising crews. While focused teams began to carve out early leads, the competition remained tight across every racing class, with crews wrapping up the day at The Hut at Little Jumby, a beloved destination on Antigua’s northeast coast.
Light winds dominated the third day of racing, compressing the fleet and shifting the focus from speed to tactical patience. With racing gains coming incrementally, many crews took advantage of the slow pace to socialize on the water, while cruisers enjoyed sunbathing and swimming before heading to the Heineken Riddim and Tides Beach Festival at Ffryes Beach for an evening of live music and local food.
The fourth and final race day delivered ideal, consistent breeze for the homeward leg from Antigua’s west coast back to English Harbour. Competitive racing fleets faced a challenging upwind beat in the final miles, while cruising crews maintained a relaxed Caribbean pace, stopping to explore scenic beaches and hidden coves along the way before completing their full circumnavigation of the island.
The closing prize-giving ceremony was held at Nelson’s Dockyard, a UNESCO World Heritage Site, with sweeping views of the centuries-old Fort Berkeley Gunpowder Magazine and the iconic limestone Pillars of Hercules. Competitors mingled among the historic stone structures, sipping local Antiguan rum and enjoying a set of Caribbean rhythms and classic rock from the 17-61° band before awards were distributed.
Organizers opened the ceremony by thanking title sponsors, community partners, and more than 50 dedicated volunteers whose work made the event run smoothly. Top honors went to the crew of *Kali*, racing under the name Kermode-Grizzly led by Great Lakes skipper Chuck Bayer. The team dominated CSA Class 1 all week, taking both corrected and line honours across all four days of racing to claim the event’s most prestigious award, the Lord Nelson Trophy. Calling the win a once-in-a-lifetime achievement, Bayer said he was deeply honored to join the ranks of legendary sailors whose names appear on the iconic trophy.
In CSA Racing Class 2, the Dutch crew of Contigo Team HI-1 secured an impressive four straight first-place finishes, holding off stiff daily competition from other teams in their class. Skipper Rien van der Post joked that the crew’s most cherished win came on the final day, when they beat the official Race Committee boat to the finish line – a first for the team, which normally races traditional Lemsteraak ships back home in the Netherlands.
Bernie Evan-Wong, sailing his Mumm 36 *High Tension*, claimed victory in a closely contested CSA Racing Class 3. Evan-Wong credited his crew’s steady focus through wildly shifting conditions, noting that a bold tactical call on the final day made all the difference. “We did a lot of upwind sailing, and our strong point is off the wind, so we really had to work hard,” he explained. “On the last day, we managed to stay on the edge of a squall, play the shifts, and then tack out at just the right moment, and in the end, that’s what won it for us.”
For the Multihull CSA Class, the classic 1987 Condor 40 *Troika*, co-owned by Sam Masterman, took home the Governor General’s Cup. Masterman praised the event’s new format and course design, noting that the structure created a fun experience for every skill level. “We had two to three crew on board, depending on the day, and it was a mix of racers and non-racers,” he said. “The way the courses were set up meant that everyone was able to have a good time whether they had a lot of experience or only a little.”
Beyond class titles, a series of special awards recognized outstanding contributions to the spirit of Antigua Sailing Week. The Jan Santos Trophy went to Neal Charles, a behind-the-scenes volunteer whose tireless work ensured the event ran smoothly. The Caribbean Sailing Association Travellers Trophy was awarded to *Apollo* owner Donald Nicholson for his consistent participation in regional sailing events, while Katy Campbell’s *Panacea X* claimed top honours in the Race Charter division for the second consecutive year. The event also highlighted its youth development work, awarding the Youth Trophy to Ashley Joshua, who progressed through the organisation’s Youth to Keel programme to compete this year aboard *Eira*. The Women’s Trophy went to Sanne Bast of *Ilios*, recognizing her commitment to the regatta both on and off the water, from welcoming visiting media to helping restore and race her team’s boat.