Antigua Sailing Week Changes Tack, Returning to Its Destination-Focused Roots

“Ready to tack!” skipper Jérôme Delire shouted through 20-knot winds as Impala’s navy blue hull heeled dramatically, its jib trimmed for close-hauling, beneath the edge of rolling clouds. 

Hosted aboard the 2023 Hanse 588 for the final day of racing at Antigua Sailing Week (ASW), I joined her crew in scrambling across the beamy aft to the windward rail.

Despite being drenched from driving rain, all six of us were smiling from ear to ear as we passed between the two orange buoys marking the finishing line. Soon enough, the sun peeked through; it is the Caribbean, after all. 

Impala may have missed out on a third-place trophy, placing fourth overall in the CSA (Caribbean Sailing Association) 1 class of the four-day sailing event. However, its owners and crew couldn’t have been happier with the results of their first ASW participation with this boat. 

“Racing is such an adrenaline rush,” says Anne-Valérie Corboz, who co-owns the 58-foot yacht with her husband Alain-Philippe Poncelet. “We didn’t buy this boat with a plan to race it. But it’s so much fun!”

Celebrating its 57th edition in late April 2026, ASW has rediscovered its destination sailing roots. The event dates to 1968, when Howard Hulford, the owner of iconic resort Curtain Bluff, and a handful of fellow hotel owners decided to stage a regatta in an effort to extend the tourism season. As the years passed, ASW evolved into an event that attracted a mix of performance and cruising yachts. To meet the needs of pure racing boats, 2026 saw the launch of Antigua Racing Cup, a four-day coastal racing event in steady trade winds off the dual island nation’s south coast. 

ASW President Alison Sly-Adams said the island’s popularity among cruising boats was one of the reasons a decision was made to create a different type of event. One that was more a circumnavigation of the Lesser Antilles island, in which boats could choose to sign up for a leisurely rally or point-to-point racing with virtual markers thrown in for a little excitement. 

“This is about experiencing the coastline—sailing during the day and partying at night,” she said. 

“At ASW, every afternoon is lay day. This is lifestyle sailing,” said Sly-Adams, referring to the rest day crews previously enjoyed midway through the event. “You can fly in to race and enjoy the shoreside parties for the four days and fly out, or you can stay on and do some cruising afterwards.”

ASW’s marquee social event, Reggae in the Park, kicked off the fun two days ahead of racing at an outdoor venue, where Antiguan reggae, dancehall, soca and afro beat artists performed, including Empress and Bless Eye, followed by Jamaican roots reggae singer Luciano. “ASW allows sailors to soak up Antiguan culture,” said Sly-Adams.

For sailing devotees, whether novice or experienced, ASW also offers an opportunity to crew with vessels carrying history in their hull and a strong racing pedigree. One such boat is Ilios, a classic two-masted Swan 65 built in 1973, an entire five decades before CSA 1 rival Impala. For Sanne Bast and her husband Marijn Lemmers, it was their dream boat. Two years ago, they purchased it in Trinidad and carried out an extensive overhaul. Today, they offer individual berths—a pay-to-play model—for crew interested in racing in Caribbean regattas such as ASW.

Of the 28-strong fleet, elegant ketch-rigged Ilios was certainly the most eye-catching. Designed by Sparkman and Stephens and built by Nautor Swan in Finland, she was created to be sailed fast. Sister vessel Sayula II was the first boat to win the inaugural Whitbread Round the World Race in 1974, which later evolved into The Ocean Race. 

And while the competition on the water between Impala, Ilios and their six other class competitors might have been tough throughout four days of racing, a different story played out shoreside each afternoon. 

On day one, at leafy, uninhabited Green Island, master griller Joyce and her team cooked up a storm, preparing local lobster, fish and chicken for famished barefoot sailors. Winds might have been a light eight knots on the short run from English Harbour but the sun was out and the seas were flat. Once sailors stepped onto the island’s sugar-sand beach, it was smiles all round as they raised a toast to the first day of racing with English Harbour Rum, a uniquely Antiguan libation imbibed incessantly throughout ASW. 

That day, I had been invited to race with Peter Blunden, the Halifax-based owner of Canadian-flagged Life of Reilly III. His sleek, grey Dufour 500 GL is fully kitted out for cruising, including a well-stocked wine cellar and frozen filet mignon. Together with Peter’s son James and friend Glenn Richard, all dressed in royal blue sailing shirts emblazoned with the boat’s name, we shared a good post-race laugh. After misreading the race instructions, we had reached the start line that morning around 90 minutes too late. Peter wasn’t phased in the slightest. “Well, at least we’ll do better in the next races,” he quipped, as we savored the shade of the bimini. 

Day two saw the fleet race a 17.2 nautical-mile course from Green island to Little Jumby Bay, off Maiden island, in eight to 15 knot winds blowing from the Atlantic. Impala hoisted a hot pink asymmetrical spinnaker with an image of a black impala, taking advantage of light winds. Water taxis and dinghies relayed sailors to shore for a lively party at beachside bar-restaurant The Hut, that lasted till late. 

But it wasn’t just ASW crew who were intent on having fun. An enthusiastic contingent of spectators showed up, thrilled to get close to the action aboard a catamaran, operated by local charter operator Wadadli Cats.

Kaiya, 23, visiting on holiday from Maryland with five family members and friends, said her Antiguan-born mother Charm had been trying to convince her to attend ASW to enjoy the social aspect of the event. “It’s the big week of the year in Antigua, where you can meet people from different countries,” Kaiya said, as she cheered on crews. “I would love to go sailing!”

Alighting at long, lithe Ffryes, a popular beach on the island’s west coast, the group were quick to get into the swing of things at a beachside party. Locals turned up in powerboats, anchoring alongside the sailboats. Vendors offered a wide array of local dishes, including jerk chicken, seasoned rice, and goat water. Reggae and soca tunes, along with 80s and 90s hits, blasted across the sand as sailors danced till late. 

“This is my first time in Antigua. It’s really beautiful and the event is so well-organised. People are very friendly,” said Anne-Valérie.

“It’s great to race in a regatta and discover the island. It makes us want to come back to explore more. I loved that everyone was in their swimming trunks and swimsuits on the beach, rather than in a bar.”

Day four saw racers and rallyers return to historic Nelson’s Dockyard, in English Harbour, where the course had begun, launching the round-island event to the sound of a steel drum band. Beyond trophies for race winners, prizes, including multiple bottles of rum, were given to crews wearing the most phantasmagorical sailing gear. Shirts illustrated with tangerines, lemons and lime, pink jellyfish earrings, and illuminated capes evoking bird wings counted among the most creative outfits crews conjured for the final prizegiving ceremony. 

Janne Kraak, racing aboard a chartered Dehler 44 Westwind with an all-female Dutch crew with the exception of the skipper, said she wasn’t initially aware of the ASW format but enjoyed the fact that they could experience some of the island. “It’s not such a big event, so you spend the day sailing and then the evening getting to know the other crews,” she said. 

Within a few short days, many of these sailors had clearly become fast friends. Clinking glasses of rum punch, they indulged in light-hearted rivalry and made plans to reconnect at next year’s event. And, as cheers rang out into the warm night air on that last evening, it was clear everyone was a winner. 

Where to Stay 

Curtain Bluff 

Featuring two palm-studded beaches, this tranquil, five-star boutique hotel on the southwest coast is an Antiguan icon. As part of an ongoing refurbishment, the Relais & Châteaux member’s suites and the beloved beachfront Sea Grape restaurant have been thoughtfully updated while retaining a spirited Caribbean vibe.  

Carlisle Bay Antigua

Framed by lush rainforest, this sophisticated, family-friendly resort sits on a pristine beach in the southwest. London-based designer Miminat Shodeinde has reimagined the interiors of 87 suites in soothing neutral shades within the context of renovations due for completion in 2027. 

Where to Dine

The Hut, Little Jumby 

Refined Caribbean cuisine with a focus on fish and seafood, ranging from mahi mahi crudo to scallops and pork belly, is served with ocean views at this hip beach restaurant and bar on Little Jumby island, where parties are regularly held.

Bushbungalow

Chef Jermaine Jonas trained in NYC and Bali before deciding to return to his beloved Antigua. He crafts thoughtful plant-based, minimal-waste cuisine with local and regional produce for small groups of guests, literally in the welcoming garden of his home.

Trappas

Giant flowers adorn the walls of this longtime sailor favorite in English Harbour, owned and operated by Caroline Tranter and known for hearty, traditional fare and strong cocktails.

Dennis Beach Bar and Restaurant

Located at the northern end of Ffryes beach, this rustic bar-restaurant draws locals and visitors alike for smoky chargrilled ribs and even pigtail. 

What to See

Shirley Heights 

From this lookout atop a hill in the south of the island, take in views of English Harbour and Falmouth Harbour and don’t miss the regular parties featuring a steel band and BBQ.

Nelson’s Dockyard

A UNESCO World Heritage-listed site and working marina, Nelson’s Dockyard was built in the 18th century within a sheltered bay to offer shelter from hurricanes and repair ships. Georgian-style naval buildings still exist today, many serving their original function. 

Devil’s Bridge 

Located on the island’s southeastern coast within a national park, this dramatic rock formation resembles a bridge. Devil’s Bridge is not merely a natural phenomenon sculpted by howling wind and crashing waves. It also marks a dark period in Antigua’s history. It’s said that enslaved people would run to this point in a bid to escape. When they realized there was nowhere to go, they chose to jump into the sea and drown, rather than remain captive.