Inside Antigua Sailing Week, An Epic Yacht Racing Spectacle

“Everyone here is on the same level, whether you come in flip-flops or on a private jet. We’re here for the sailing.”

Ed Whiting

I first went to Antigua in 1997. Enticed by a siren beauty to race Antigua Sailing Week, the biggest regatta on the Caribbean calendar. My eyes were opened wide to the size of dinner plates. Not just by the sight of Shana in a bikini piloting the spinnaker on an 80-foot Swan yacht. But also by the special club of ridiculous wealth and passion I had stumbled upon. A heady mix of kings and pirates: yacht racing. 

Antigua takes its name from Santa Maria de la Antigua, a Church in Seville, in Spain, so named by Christopher Columbus when he landed there in 1493. The British colonized Antigua in 1632 and it remained in British hands until independence in 1981. English Harbour was developed as a base for the British Navy, serving as headquarters of the fleet of the Leeward Islands during the late 18th century. 

Ed Whiting

In the late 1960s, classic yachts out of English Harbour began racing to Guadeloupe at the end of the year’s Caribbean chartering season. Eventually, in 1967, this informal end-of-season race became Antigua Sailing Week. All the entrants were classic yachts. But over the next 20 years or so modern racing yachts began to outnumber classics. By 1987 the classics had been relegated to Cruising Class 3. So that year, captains Uli Pruesse and Kenny Coombs hosted a rum-fueled party aboard the magnificent 114-ft. schooner Aschanti of Saba. And plotted a mutiny. The mutiny was successfully executed, and the Antigua Classic Yacht Regatta was born. 

Time moves along in its inexorable way. Fast forward to 2019. I’m at Galley Bay Resort, my first trip back to Antigua since 1997. Shana in her bikini on the 80-foot Swan is long gone. But a story for another timefilled with Hanky Panky cocktails, charity auctions, Aston Martins, models, and Miami has led me back here. 

Ed Whiting

I’m in the resort’s Seagrape restaurant, enjoying their fantastic barbecue. Chewing on a crunchy, juicy ear of suckling pig, and pondering how rejuvenated I feel after a few days here. It’s not quite rehab. But it certainly feels as if it’s healing me. 

I’ve become fast friends with the barkeep at each of the resort’s four bars. And consumed a lake of beer, rum, and wine. My favorite lunchtime tipple is a concoction of rums (white and dark) made in a blender and served with an umbrella in a curved glass. Nuclear pink in the bottom half. Coconut-meat white on top. Rather appropriately they call it a Miami Vice. It does a fine job of taking the edge off the tingle in my slightly frazzled dermis, and readies me for more unbridled sun worship of an afternoon. Perhaps interrupted by a snorkel or three with the tropical fish on the coral, a short distance off the beach.

Ed Whiting

I’d arrived full of New York City. Perhaps brimming over with New York City. Which is to say, in need of a complete disconnect from electrifying overstimulation. After a Boeing 737-800, a taxi, and a golf cart across a lagoon, I am in situ. Glazed over like an overcooked creme brûlée staring out from my room past my terrace to palm trees, white sand, and picture-perfect turquoise waters. 

Historically–at least before the pandemic hit–my trips had been a little different. Crazy weekend adventures to the dark heart of Africa raising money for elephants and conservation. Or hops to Monaco to watch Formula One cars battle the Grand Prix through rosé-soaked glasses on a yacht. So while my biggest question for the day is which on-campus restaurant to frequent, I get to reminiscing. 

Lucas Noonan

And as New York is slowly rubbed off by a salve of smiles, good spirits, good food, sunshine, sea and snorkeling, I find myself relaxing and enjoying it. And pondering taking a proper run at yacht racing in Antigua again. Perhaps even entering the legendary Antigua Classic Yacht Regatta. I leave with this thought in mind. And ponder how we can launch a campaign to race the Antigua Classic. 

In order to be eligible to race the regatta, your yacht must be a monohull and fit into one of the permitted categories: Vintage, Classic, Traditional, Historic, Classic GRP, Spirit of Tradition, Dragon, or Tall Ships. In other words, boats that are original pre-1976 monohull yachts, or boats that replicate the qualities of such yachts. So we needed to find the right boat. 

Ed Whiting

In early 2020, my rosé brand, Quinn Rosé, which I have been drinking since 1982 and importing since 2014, was appointed the official rosé of the Antigua Classic Yacht Regatta. So it looks as if we have the excuse we need to enter the regatta; and as if the stars have aligned, and it’s going to be our year. We’re going racing. We may not be kings or pirates, but we’re certainly gentleman rogues. 

And as regatta founder, Kenny Coombs, likes to say, “Everyone here is on the same level, whether you come in flip-flops or on a private jet. We’re here for the sailing.” We find the race-winning classic yacht Blue Peter—designed by Alfred Mylne in 1929, and built by W. King & sons in Burnham-on-Crouch in 1930 in England. And team up with Captain Mat Barker to race flying our proprietary Smoking Skull flag. Mat bought Blue Peter in 1999 on a break from trading derivatives. 

Ed Whiting

Four years later he decided he was probably unemployable, and started selling spots onboard to race regattas with him. Seemed like our kind of lovable rogue. He’s won regattas in Antibes, Cannes, Palma, Barcelona and Antigua, so perfect for our needs. We set up our onshore accommodations at The St. James Club, owned by the same guys who own Galley Bay Resort. And shipped a lake of rosé to Antigua while we got cracking on team kit— polos, caps, and paraphernalia. 

Then Covid-19 hits. The world is shut down. And the 2020 regatta is cancelled. Memories surface of grinding winches, inhaling rum punch, and adding weight to the rail in 1997. But we’ll be back, hoisting the flag, and inhaling the official rosé of the Antigua Classic Yacht Regatta in 2021–Quinn Rosé. 

By the time you are reading this, we’ll be on another lark, sailing the Blue Peter up from Antigua to New York and Nantucket. Flying the Smoking Skull. And toasting each day as we head north for the party of all parties, when we arrive and the Covid-19 mist lifts. Drop us a line—we may even be able to wrangle you an invite.