Racing the BVI Spring Regatta After a Decade Away from It

The Sailing Festival comprises the 37-mile round-Tortola race and the Scrub Island Invitational, a 12-mile upwind race with a barbecue, music and pool party at the island’s resort. Andrea Azzopardi/Tidal Pulse Media/BVISR

A 20-knot gust tempers the Caribbean sun, but I can still feel it burning my thighs as I lean forward on the rail, throwing arms and legs overboard on our racer-cruiser Blueprint, a Beneteau 36.7.

Conditions are deemed favorable for the first day of the BVI Spring Regatta, which means lots of wind and lots of shouting, though not from us. Sailboats are tacking all around us. Charcoal sails, turquoise shirts and everyone (except me) wears a bright red cap from sponsor Mount Gay Rum. Sadly, I lost mine overboard, but I am wearing a life vest, and by the looks of it on the other boats, I am the only one. Apparently, it’s just not the racing way.

The five-minute gun sounds. I feel nervous. It’s been a decade since I’ve raced in a regatta.

“Stop!” the skipper, Rory Johnson, calls out.

I crane my neck toward the cockpit and assess the status of my crewmates. Misty and Paige are crouched by the winches. Kent seems relaxed on the helm in spite of his broken toe. Jeff, next to me on the rail, has his eyes trained on the 30 boats on the horizon, a mix of everything from bareboats to performance trimarans.

“Hove to!” Rory calls.

The racing classes set sail at different times, with performance multihulls up first. Andrea Azzopardi/Tidal Pulse Media/BVISR

Our crew, who have only known one another a day, know exactly what to do. We tack, leaving the headsail backed, and Blueprint slows to a halt.

“Right, caps off. We’re going to sign them.”

Rory whips out a black marker. While all around us, sailboats are jostling for position, we float calmly, a few boat lengths from the mix, scribbling our names on one another’s hats. My nerves evaporate. In fact, I’m more concerned that I wrote my name on the top of the skipper’s cap, rather than on the visor like everyone else did, but he doesn’t seem to mind.

Clearly, Rory is no ordinary skipper, but this is no ordinary regatta. We are possibly in the most beautiful cruising ground in the world: more than 60 volcanic islands (and one flat coral one) fringed with white beaches and palm trees. Some of the islands form course markers. Yes, we are racing, but Rory reminds us we are here to have fun.

A British master mariner, Rory is also an instructor for Ondeck Sailing, and his paying crew are getting their first taste of a Caribbean regatta. Jeff Irving and Paige Jones from Virginia are ASA certified to 101 and 103 but have not raced before, whereas Misty and Mike Wilmot race every week in Connecticut, mostly against monohulls.

“Catamarans haven’t caught on there yet,” says Misty, who heard about the BVI Spring Regatta through the vacation section of the ASA.

Scrub Island remains a popular respite for cruisers. Andrea Azzopardi/Tidal Pulse Media/BVISR

Kent Lowell from Hermosa Beach, California, owns a Catalina 34, a rental boat in a fleet that he helps manage. He races in the Los Angeles harbor area on Thursday nights. This is his first regatta.

Shoreside, there’s entertainment in a festival-style village with a stage and bar, as well as a pool, eateries and a beach. The BVI Spring Regatta is what the ASA describes as a sailing vacation, Kent says. It has a cruising division and is open to anyone.

That said, he feels the term “racing experience” would be more apt.

“A vacation is what I did in Croatia: a luxury yacht with a private cabin and three meals a day cooked by a professional chef,” he says. “Here, I’m sweating and aching from standing all day.”

But even so, he says he’d 100 percent do it again. Kent is a management consultant, and he has been carefully observing the skipper.

“We have two highly experienced racers and two new ones, and so he has to manage a dispersed level of expertise,” he says. “Most of what he’s doing is actually managing safety: safety of the crew, safety of the boat and safety of other vessels. Instead of racing out there and getting all excited before the start, which is what I’ve been doing for five years, he brought us out dead slow, hove-to and calmed everyone down. I’m stealing that idea.”

The author explores Virgin Gorda’s iconic Baths National Park. Ali Wood Freshman Nerves

In the marina village this morning, when everyone was glugging back smoothies and chomping breakfast bagels, I’d felt like a freshman wandering alone through campus. Daunted by the huddles of sailors in shimmery tops and wide-brimmed hats, I’d tracked down the Blueprint crew at Island Roots Cafe and introduced myself. When I asked the skipper what job he’d like me to do, he’d said, “Nothing. Best to just leave the crew to it.” My heart sank, but they were a crack team already, and I was the newcomer.

Now, just minutes from the start, Rory has changed his mind. “I couldn’t just let you sit there,” he says.

For the upwind leg, I’m bowman, a job I share with Jeff. Each tack, I’m climbing across the coachroof on my hands and knees, careful to duck the swinging boom. On the high side, once the tack’s complete, I scurry forward, keeping my center of gravity low to skirt the genoa over the guardrails while Misty grinds it in. The decks are wet, and several times I slip, steadying my footing on the 2-inch toerail. I’m glad to have my life vest, and when Ondeck’s sister boat Eira races past, I note that its crew is all in life vests too.

“Good job!” Rory shouts. The crew are cheering me on, and I feel very much a part of the team.

The racing classes set sail at different times. First is the Performance Multihulls, led by TF10 foiling trimaran Thunder and Lightning, the Gunboat 72 Layla and the 63-foot Nigel Irens trimaran Sophia. They are the kinds of boats I’ve only ever seen in magazines. To watch them fly around the course is thrilling.

Trailerable, foldable Corsair trimarans dominate the Sports Multihull class. A 31-1D, Airgasm, leads the fleet, followed by F-31 Ting-A-Ling II and Sprint 750 Lucky 7, crewed by a father-daughter team.

Kent Lowell takes the helm, despite recovering from a broken toe. Ali Wood

I’d always assumed these events were for serious racers: zinc-sunblocked men with bulging biceps and designer shades. There are plenty of professionals around, including Olympian Terry McLaughlin, America’s Cup winners and J/105 North American champions, but there are many amateur sailors too.

Most of the competitors are friends and families on vacation. It’s why the regatta has a bareboat division, and allows time for lay days. Sailors can visit the sleepy coral paradise of Anegada, or explore the tidal pools of Baths National Park, with its rocks that look like giant marbles dropped from the sky.

Hurricane Memories

Today’s race is around Tortola, which I’m excited to see from the boat because yesterday, we toured it by car. Our host, Harmony Turnball, swung around hairpin bends with the ease of a Formula One driver.

“The roads are a bit extreme. It’s why my mom doesn’t visit me,” she said with a laugh as we descended at an angle I’d never experienced, passing dainty colonial homes toward Long Bay, a mile-long stretch of affluent villas and postcard-white sands. We returned via a roadside shell museum and Harmony’s beachfront house. She explained how she’d escaped Hurricane Irma in 2017.

“There was a 30-foot wave,” she said. “I was swimming, my dogs were swimming, my son was swimming; he was 11 at the time, and now he’s in the U.S. Coast Guard. You have to know how to swim here. Really, you don’t need to live by the beach if you don’t swim.”

Misty Wilmot aboard Blueprint is an experienced racer back home in Connecticut. Ali Wood

Harmony’s story of survival is one that many islanders share, including BVI Regatta sailor Richard Wooldridge, competing on his trimaran Triple Jack. The Category 5 hurricane destroyed more than 80 percent of the homes. Wooldridge and his young family sheltered in their bathroom.

“Afterwards, when we opened the door, three walls were completely gone,” he recalls. “The glass from the sliding doors was everywhere. … No one knew we were alive until three days later. There were no phones, no services. The roads were blocked. Every school had gone.”

When Richard finally made it to Nanny Cay, he found the marina full of sunken wrecks.

“I was certain we’d never see Triple Jack again, that she’d been blown away,” he says. “There were big cats flying in that storm. The trees were polished white, the bark sandblasted by 200-mile-an-hour winds.”

The blustery upwind start required a reefed main. Ali Wood

But there she was, upside down on the bridge, her mast broken in four places, coachroof destroyed and the sponsons barely hanging on.

Richard, together with co-owner Steve Davis, couldn’t bear to part with the boat they’d owned for 20 years. With the help of friends and family, they spent five years rebuilding Triple Jack at Nanny Cay, and here she is today, racing once more in the BVI Spring Regatta.

Spinnaker Launch

Blueprint is sailing well, and as we round the rocky outcrops of Tortola, the wind fills in from behind. Misty, an experienced racer, jumps to the bow and explains to Jeff how to launch the spinnaker. It’s the first time they’ve done this on Blueprint, and they nail it. No preventer, just me (slightly terrified) on the mainsail as we surf dead downwind. A couple of times, I sheet in fast, arm over arm, as Rory taught me, the boom teetering overhead, but never flipping.

We come in sixth and would have done better if not for some confusion at the finish line. Not to worry, this was a learning experience, Rory says. The main thing is we had a brilliant time.

“We doused the spinnaker and got it up and down again,” he says. “We really worked well as a team, and now we’re getting into the nonverbal.”

Competition heats up in the bareboat division. Andrea Azzopardi/Tidal Pulse Media/BVISR

We join the crew of Eira (also racing with Ondeck) for a debrief. Seated in a circle, we’re asked to give one word that sums up our feelings. I opt to go last, which means I have to come up with something a dozen other people haven’t said. “Cherished,” I blurt out, feeling my cheeks redden.

Is that too much? Somehow, “accepted” or “included” doesn’t capture the intensity of it all. I’m grateful to Rory for making me one of the crew. I feel so close to these people who this morning were strangers. Isn’t that a great thing about sailing?

I return to the marina village, where euphoric sailors spill rum punch as they dance to live reggae. It’s been a thrilling day. I’ve learned new terminology such as “railmeat” and that to “burp” a line is to ease it through the clutch just a tiny bit. I know that a “bullet” is a win, though confusingly also a gust, and yes, I really am feeling cherished.

Now that I’ve found my tribe, I am relaxed, ready to join in the celebrations, and can’t wait to do it all again tomorrow, on a new boat and with a completely different crew.

All smiles among the Blueprint crew after the Round Tortola Race. Andrea Azzopardi/Tidal Pulse Media/BVISR BVI Spring Regatta

The BVI Spring Regatta & Sailing Festival is a two-part event. The Spring Regatta is three days of racing around marks and islands. The Sailing Festival comprises the 37-mile round-Tortola race and the Scrub Island Invitational, a 12-mile upwind race with a barbecue, music and pool party at the island’s resort. Sailors can participate in all five races, or either the two-day festival or three-day regatta.

While many sailors compete in their own boats, some charter a bareboat or an individual berth with other paying crew and a professional skipper.

All boats are rated in accordance with the Caribbean Sailing Association rules. The event is organized by the Royal BVI Yacht Club with various classes. The courses use a combination of islands and buoys depending on conditions, ensuring the right classes get the right courses and plenty of variety.

Most entries come from the United States and Caribbean, but also competing in the 2026 regatta were sailors from Puerto Rico, Canada, Switzerland, Germany, the UK and Finland.

Dock space and accommodations are available at Nanny Cay. There are also marinas a short taxi ride away in Road Town, Manuel Reef and West End.

Private villas and apartments are also spread across islands, with water taxis being the main mode of transport.

Charter Options Whole Boat 

Charter prices vary in the BVI according to the season, but a Sunsail bareboat, for example, starts at $4,314 for seven nights for two passengers.

• Sunsail offers Beneteau or Jeanneau monohulls, and Robertson & Caine and Lagoon catamarans, from 32 to 52 feet. sunsail.com
• The Moorings offers Beneteau or Jeanneau monohulls and Robertson & Caine catamarans from 38 to 58 feet. moorings.com
• BVI Yacht Charters offers catamarans and monohulls from 31 to 55 feet. bviyachtcharters.com
• LV Yachting has a range of charter options from Grand Prix racing yachts to racer-cruisers. For the BVI Spring Regatta, it offers a Grand Soleil 46 and J/133. lvyachting.com
• Horizon Yacht Charters offers Diam 24 trimarans at 24 feet long. horizonyachtcharters.com
• Caribbean Races offers a 40-foot J/120 racer-cruiser. The owner’s representative must be present on all races. No overnight accommodation. caribbeanraces.com

Individual Berth

When chartering a berth, you’ll be on a boat with a qualified skipper and other individuals, friends or couples. An individual berth for five days of Caribbean racing on Ondeck’s Farr 65 Spirit of Juno, for example, would cost about $2,300.

• Panacea X is a Salona 45 racer-cruiser. seatoskysailing.com
• Emily of Cowes, a 45-foot Rob Humphries design, is available for whole boat and individual charters. emilyofcowes.com
• Escapado is a Beneteau First 40.7. sailracingacademy.org
• Spirit of Juno, a Farr 65, is available for whole boat and individual charters, as is a Beneteau First 36.7. 
• ondecksailing.com
• Various yachts are available from Ocean Racers for skippered charter or individual berths. oceanracers.net
• Cannonball, a 73-foot Mini Maxi, plus a Volvo 70 and Swan 45, are available for whole boat or individual berth charter. sailracecrew.com

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