FEATURE
Antigua Sailing Week: Embracing the winds of change We take a nostalgic look back through the decades and find out what’s next for the hallmark event
T ake a peek at old photos of Antigua Sailing Week and the intoxicating ambience is evident in every grainy, faded image. Competition on the water was fierce, the offshore antics exuberant. The regatta’s halcyon days were heady, hedonistic and heaving with people. Sailing as a sport has seen momentous evolution over the years, from a rugged, manual pursuit into a highly automated, tech-forward and comfort-focused lifestyle. The shift from traditional monohulls towards catamarans means less people are racing, while global financial pressures, and a pandemic, have altered the way we socialise too. What hasn’t changed is Sailing Week’s position as one of the world’s most beloved regattas. Today, participants may be fewer but they’re no less ardent. Many old-timers still flock to enjoy the event’s insouciant, nostalgia-evoking vibes. But Sailing Week is simultaneously attracting a fresh clutch of hardcore competitors with high- performance vessels, ready to battle it out on the water. Organisers have been embracing the winds of change. April 2026 saw a return to the regatta’s roots with social functions scattered across the island, rather than concentrated in English Harbour, while the inaugural Racing Cup held 10 days prior ushered in a new era of heightened rivalry. “It became clear that it was better to have two separate events - one that focused on adrenalin-fuelled racing, and one for people who just want to enjoy sailing and experience the destination,” explains Alison Sly-Adams, a key organiser of Sailing Week for two decades. The 21 boats that took part in the Racing Cup relished in tight, nail-biting courses, with several entrants making it to the finishing line within seconds of each other. For the 28 vessels that competed in Sailing Week, races elicited the easygoing conviviality of yesteryear. For the wider public, Sailing Week’s retro format was a wistful nod to the days of old when rambunctious crowds would line Dickenson Bay and Jolly Harbour to soak up the festivities. Its condensed configuration – with four different locations in
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