Antigua Sailing Week Welcomes Novice and Pro Yacht Crews with Open Arms

As the barefoot, coolheaded Irish skipper, David Hanks, expertly maneuvred the 65-foot sailing yacht in winds gusting up to 17 knots, he hustled between the gleaming hulls of its four big boat class rivals eyeing a narrow race start line during Antigua Sailing Week (ASW), mainsail trimmer Ryan Thompson was a picture of concentration. 

Although brand new to sailing, by race day two, Thompson was taking his role aboard the Farr design, Spirit of Juno, extremely seriously. He was already well aware that the hectic race start could determine how the boat placed. Thompson kept his ears peeled for instruction from a more experienced crew member while training his eye on the vast black sail. 

Based in sailing mecca—San Francisco—Thompson told Worth he was “almost embarrassed” to be in his 50s, yet know nothing about the pulse-quickening sport.

Thompson’s first taste of sailing would be aboard Spirit of Juno with Antigua-based race yacht charter company OnDeck Sailing and 16 individuals he’d never met before. It’s no small feat to try to grasp the basics of sailing during a demanding, week-long regatta. Other yachts, like CSA Monohull Racing 1 division winner TP52 Hooligan Racing, are staffed with professional crew members who have been racing for years and regularly train together. But Thompson demonstrated that you don’t need to be an experienced sailor to relish the thrills and spills of one of the Caribbean’s most welcoming and best-loved regattas.

A Rapid-Fire Learning Experience

It was longtime colleague and “adventure buddy” Charlie Cornett, 59, a consultant from Orlando, Florida, who persuaded Thompson to join him to go yacht racing in the twin-island eastern Caribbean nation. 

“Charlie said I would learn a lot, we would have fun, and promised me a lot of rum … The opportunity to hang out with Charlie, travel somewhere new, and learn something was appealing,” he told Worth. Thompson said he reveled in “the absolute peace of the surroundings … the swells, wind, sun, and views.” Not to mention that “The energy around the start of the race was incredibly exciting … I think social strata sort of melt away and we’re just people on the water, striving a bit toward something.” 

Photo by Carlo Raciti

Thompson has already applied a deceptively simple concept that David voiced a few times while instructing crew, in his professional life: “‘It’s perfect or it’s not … slow down’.  I’ve repeated that at work a few times. It’s just business instead of sailing,” Thompson said.

Cornett and Thompson had taken several trips together but had never sailed. “I admire his energy towards taking on this challenge and completely embracing it. I think he even got some votes for crewmember of the week, which doesn’t surprise me. We are always on the lookout for our next idea,” Cornett told Worth

Designed and built in 1999 for the Millennium Round the World Yacht Race, Spirit of Juno may be older and heavier than its fast, high-performance competitors but it still has plenty of fire in its beamy belly. Despite facing stiff competition, Spirit of Juno secured fourth place overall, ahead of arch-rival Fatjax, a 63-foot Shipman, in its division.

An Explosion of Interest 

Over the past three years, sailing clubs in the U.S. and around the world have seen unprecedented growth in membership, with people signing up for sailing lessons and yearning to experience the freedom of harnessing the wind and exploring destinations by sailboat. 

For a pure adrenaline rush though, nothing compares to thrill-a-minute yacht racing. You don’t need to be an Olympic-class sailor or even own a yacht to join a race crew. Whether you’re a complete newbie, intermediate sailor, or experienced in yacht racing, there are plenty of regattas in the Caribbean open to sailors of all levels. Antigua alone hosts the Antigua Classic Yacht Regatta, Superyacht Challenge Antigua, and the RORC Nelson’s Cup Series, which was held this year for the first time and encompassed the RORC Caribbean 600. With Hanks at the helm, Spirit of Juno triumphed in the IRC Two category.

A Regatta to Be Reckoned With

Antigua’s premier sailing regatta might not attract St Maarten Heineken Regatta’s 20,000-plus visitors or draw the multi-million dollar sloops, ketches, and schooners of St Barths Bucket Regatta, but it has history and holds clout in the yacht racing world. Dreamed up by hoteliers in 1968 in a bid to extend the winter season, the prestigious event is also the curtain closer for the region’s yacht racing season spanning January to May. 

Photo by Carlo Raciti

With sailors from 18 nations, ASW kicked off with the stand-alone 52-mile Peters & May Round Antigua Race, however, light winds forced race organizers to shorten the course this year. With each race day that passed, the breeze picked up, powering a rainbow of gennakers and spinnakers across the varied race courses. Among the most eye-catching was the Antiguan boat NSA Spirit’s kite proudly depicting the national flag. 

Women on the Water

While yacht racing still remains very much a male-dominated sport, women sailors are proving their mettle. At this year’s ASW, women represented 25% of all sailors, among them America’s Cup competitor Suzy Leach and up-and-coming Antiguan sailor, 12-year-old Imani John-Polanco. Locman Italy Women’s Race Day was dedicated to the fearless women on the water, including four all-female crews. 

I split race days between Spirit of Juno, whose crew was all-male with the exception of dynamic first mate Michelle Franklin and myself, and CSA Monohull Racing 4 division entrant Hatha Maris, a 40-foot Dufour performance cruiser owned by Italian-American skipper and sailing instructor Lyssandra Barbieri. She operates Second Star Sailing, a Royal Yachting Association-accredited sailing school based in Antigua and Pisa, Italy. I joined Barbieri and a nine-strong all-female crew, where I took the wheel, albeit briefly, for the first time during a race since earning my skipper’s license in 2017. 

“I’m really proud of you all,” a beaming Barbieri told us at our final post-race meeting. “We saw clear improvement day by day because everyone was really focused.” 

Barbieri runs a Women at the Helm program, designed by female instructors to encourage women to learn to sail in a supportive and enjoyable setting. As part of the initiative, Barbieri offers internships to Antiguan women to equip them with skills in sailing school management, training, and sailboat and powerboat maintenance, should they decide on pursuing a career in sailing or yachting.

On board Hatha Maris was soft-spoken yet determined Ryanne Small. The Jamaican-born, Antigua-raised, 20-year-old has always loved the water and developed an interest in boats while spending time at Jolly Harbour, where her mother works as a cosmetologist. She took dinghy sailing lessons at age eight until track and field swayed her attention. “I’ve always known that I wanted to become a captain. I finished high school and college but still wasn’t pleased because I wanted to be on the water,” she told Worth. But Small didn’t have the means or contacts to break into the industry.

Just over a year ago, a client of her mother’s—who owned a yacht charter—took a chance on Small and hired her. “Once I got in, it was easy to meet other people,” she said. Small now works as a freelance first mate on day charters and aims to progress to week-long charters as well as yacht deliveries to build mileage. 

Among the critical life skills Small said she had learned through sailing were teamwork and respect for fellow crew members. “Once you’re in it, you have to be committed 100%,” she said. As the first sailor in her family, Small has her sights set on owning a boat and establishing her own charter company.

Work Hard, Play Hard 

At ASW, it’s not all work and no play. Crews gather at daily prizegiving ceremonies at the Antigua Yacht Club, where local bands set the tone with uplifting reggae, soca, and calypso tunes and rum punch flows freely. 

What all crews look forward to most is Reggae in the Park, an annual highlight on the Lesser Antilles country’s social calendar. Antiguans and sailors alike gathered at Unesco World Heritage-listed Georgian-era Nelson’s Dockyard, built in the mid-1700s and later named after English naval hero Horatio Nelson, for a mid-week wind-down. Prominent Jamaican artists Protoje, Lila Iké, and Jesse Royal roused the crowd with infectious contemporary reggae tracks by the water as mast lights twinkled in the moonlight.

Following four action-packed race days, a lay (or rest) day was most welcome. I skipped the beach games at Pigeon Point Beach in favor of a swim in aquamarine waters surrounding Prickly Pear Island, off Hodges Bay Resort and Spa on Antigua’s northern coast. 

Race Yacht Charter Options

Photo by Carlo Raciti

Individual crew places can be booked on what is known as a head boat, such as Spirit of Juno, via companies like OnDeck Sailing and Second Star Sailing. Boat and race costs are covered, including a minimum of one training day, a professional skipper and mate, and lunch and drinks during racing. If you have your own skipper and crew, race-ready boats are also available for charter. 

Where to Stay

Rest is crucial when racing, so check into one of Antigua’s comely beachside resorts to relax in the shade of palm trees and cool off with a swim. Sailors seeking peace and quiet flock to The Inn at English Harbour, a refined Georgian-style boutique hotel just a seven-minute drive south of ASW headquarters Antigua Yacht Club. 

Photo by Carlo Raciti

Stay on and take some time to explore Antigua’s plethora of sandy beaches, hike through the rainforest, and sample the traditional local fare. Iconic all-inclusive Curtain Bluff, on the south coast, offers tennis, hobie cat sailing, and reef snorkeling trips as part of the room rate. In the north, celebrity hideout Blue Waters Resort & Spa features lush tropical gardens and elegant villas. 

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