The BVI Spring Regatta & Sailing Festival: Enthralling Racing and Shoreside Pleasures

Sailing fast double-handed on a catamaran near Bitter End Yacht Club, in the British Virgin Islands, I noticed the winds were less predictable than I expected. So, I was doing pretty well, taking care to trim the mainsail and manoeuvre the tiller while artfully dodging mooring balls and yachts. 

Until a sudden gust caught me by surprise, overpowering the sail and causing the boat to flip. Clearly, I wasn’t being careful enough. When I clambered back on board, all I could do was laugh at my foolishness.  

I was in the Caribbean nation, which consists of more than 50 islands, for the BVI Spring Regatta & Sailing Festival. Considering I hadn’t even stepped aboard the boat I would be racing on, it was an inauspicious start to my first participation in the annual event. I was merely having some fun on one of the Hobie Cats available to guests of Bitter End, situated in the well-sheltered North Sound on the island of Virgin Gorda. 

A cherished port of call for sailors, Bitter End has been completely revamped and is gradually reopening, since it was flattened when Hurricane Irma viciously ripped through the BVI in September 2017. The Category 5 storm left a trail of massive destruction in its wake, leveling homes, ravaging the land and destroying livelihoods. The rebuilding of Bitter End, and other outposts beloved of sailors and locals alike, stands as a testament to the resilience of the BVI people. 

Following my misadventure, I headed to the resort’s swish The Clubhouse restaurant for lunch, where I ordered my first Painkiller, not only because I needed something sweet and refreshing but also to do away with any sense of embarrassment. This classic cocktail was born in the BVI, namely at the legendary beachfront Soggy Dollar Bar on the island of Jost Van Dyke, which suffered a similar fate to Bitter End and reopened following reconstruction. Made with dark rum—usually Pusser’s, pineapple juice, orange juice, and cream of coconut and served over ice with a sprinkle of freshly-grated nutmeg, the Painkiller is as deliciously lethal as it sounds. While I rarely drink alcohol, it was hard to resist ordering this sweet temptation wherever I went in the BVI.

From the breezy indoor section of The Clubhouse, where I sampled crisp conch fritters with a spicy rum sauce to the tune of Latin-influenced house music, a sea-facing open window framed palm trees, and a quartet of Maxis docked at a jetty like a living painting. Almost two weeks had passed since the five-day invitational North Sound Maxi Regatta, in its second year, had ended in mid-March, yet four yachts, namely Wally Cento Galateia, Leopard 3, Deep Blue, and striking black V, along with several crew members had stayed on to revel in the sunshine and relaxation. 

Meanwhile, in Tortola, the BVI’s largest island and capital, Nanny Cay Marina was a hive of activity as crews prepared for the start of the BVI Spring Regatta and Sailing Festival, held in March or April. Wooden homes on stilts, boutique hotels, stores, restaurants, and cafes in shades of powder blue, candy pink, and sunshine yellow surround the marina, with pockets of green where sailors gathered at tables to savor a leisurely breakfast before heading down to the docks. With masts as far as the eye can see, I felt like I was in heaven. 

This was not only my first time racing in this event but also visiting the BVI. When the BVI secured the trademark for the phrase “The Sailing Capital of the World™” in 2025, I wanted to find out if the territory could live up to this bold claim. 

2026 marked the 53rd edition of the BVI Spring Regatta. I found myself among the hundreds of passionate sailors who had gathered from around the world to compete in what some argue are the most beautiful sailing waters on earth. 

As a Greek-Australian who has lived in Athens for three decades and spent much of that time exploring Greece’s islands, I was interested to see how the BVI compared in terms of scenery and lifestyle. And, as a sailor, albeit a newbie, competing in weekend races and week-long regattas in Greek waters, I was curious to experience BVI sailing conditions.

Stepping onboard Panacea X, a royal blue, race-optimised Salona 45, blonde, curly-haired skipper Ben Daniel welcomed me with a broad smile. Fate clearly matched me with a boat named after the Greek goddess of universal healing. 

Panacea X belongs to Vancouver-based Royal Yachting Association training center Sea to Sky Sailing. Owner Katy Campbell, an RYA Chief Instructor and lead race skipper, and her team offer cruising instruction and yacht racing training in British Columbia in spring and summer and the Caribbean in winter. Sailors can sign up for individual berth places on a pay-to-play basis to crew in Caribbean races ranging from the BVI Spring Regatta to the St Maarten Heineken Regatta.

In race one on day one, Mount Gay Race Day, we sported the sought-after, sponsor-provided red caps recognized by sailors everywhere. Panacea X darted ahead of division rivals in steady 15-plus knots and flat, sapphire-hued seas. Upon hoisting the spinnaker, the sail hourglassed but skilled bowman Flynn managed to swiftly untwist it. Race two entailed a rather hairy start, with some near-kisses between bows, but we surged ahead of the fleet once again, and scored the top spot. As we doused the spinnaker, Ben said: “Great work, everyone!” Having raced with one or two skippers who were critical rather than encouraging, it was a breath of fresh air to be led by someone with a calm demeanour, who trusted his crew and was generous in his praise. 

Not only that, we were fortunate to not only have skilled sailors and several sailing instructors on board, who knew the BVI well and clued me in on sailing and weather conditions. Also on board were two enthusiastic young dinghy sailors from Tortola who darted around the boat barefoot, excited to be racing “on a big boat”. They knew the name of every islet and rocky outcrop we passed and brought us home-baked cake. 

Jamie Grayson, a retired maritime chief engineer from Chesapeake, Virginia, who has been racing since age 12, said he thoroughly enjoyed racing in the regatta for the first time. “Panacea X is a very well-maintained, tight boat, ” said Jamie, who served as mainsail trimmer. “Sailing is enjoyable, but the other great thing is that you meet a whole cast of characters on the boat.”

Nalini Ambiavagar, a semi-retired Singapore-born GP who flew in from Wexford, Ireland, says she enjoys the camaraderie and excitement of racing. “It’s nice to have this really experienced crew to tell me what to do,” she says. “I like racing around islands rather than marks, as we have at home.”

And while I might have felt a little nervous ahead of the regatta about joining a new crew on a new-to-me boat, as I hadn’t raced in about three years, my concerns had dissipated by the end of day one. 

On day three, we were first off the blocks again, harnessing steady 14-plus knots. Crew-member Jen Kneale, who lives between the BVI and the Isle of Man in the Irish Sea, says she never needs to check the weather when she wakes up in the morning, as “it’s always easterlies, 14 to 16 knots”. Winding between Tortola, Peter Island and jagged rocks known as Dead Man’s Chest, it was a glorious feeling to see the fleet trailing behind us. With the spinnaker up, going downwind, we clocked a very respectable maximum speed of 11 knots.

Back at the docks, as racing wound up, I watched as crews from around the world exchanged hearty congratulations, lent tools to one another and shared a drink. It felt more like a gathering of friends old and new, rather than a sporting event. More like an annual gathering of individuals who have found, in these islands, their place and their people. That sense of place, of the BVI as a destination that gets under your skin.

Panacea X finished first in the CSA Performance Cruising division with seven points after scoring five first places and one second. As we celebrated our win on the podium at the lively final prizegiving ceremony and collected the trophy, our rivals, the crew of First 40.7 Popombi, who finished second with sixteen points, clapped and whooped with joy for us. I thought, there must be something in the water here in the BVI. It’s not just about the beauty of the archipelago or the thrilling racing around the islands. I realized that the BVI represents the true spirit of sailing: sportsmanship and sharing a pure love for simply being on the water. 

Getting to the BVI

This paradisiacal destination has never been more accessible. American Airlines offers several non-stop flights daily from Miami to Tortola’s Terrance B. Lettsome International Airport on Beef Island, the main airport serving the BVI. I flew in from the UK with British Airways on a non-stop flight from London Gatwick to Antigua, from which I took a short flight with interCaribbean Airways to Beef Island.   

Where to Stay

Scrub Island Resort, Spa & Marina

Situated on a private island a short boat ride from Tortola, this resort comprises 52 rooms and suites, a collection of villas, two private beaches, restaurants, a spa, and a 55-slip marina. 

Long Bay Beach Resort

Set on a mile-long stretch of powder-white sand, this 36-room resort on Tortola features oceanfront accommodations and inspired Caribbean cuisine at its restaurant 1748.

Where to Dine 

Island Roots

Arrive early to beat the inevitable queue at this popular cafe in Nanny Cay, which serves hearty breakfast burritos, homestyle cakes, and muffins, nutritious smoothies, and the best coffee in town. 

The Clubhouse

Located within Bitter End Yacht Club, this stylish, nautically-themed all-day restaurant, built from the remains of a racing yacht in 1969, turns out delectable shrimp creole and Thai-inspired grilled mahi-mahi, among other highlights.

Cardamom & Co.

This elegant fine dining restaurant, located at Scrub Island Resort, Spa & Marina, focuses on fish and seafood, with highlights including seared crab cakes, spicy grilled octopus, and Caribbean lobster in a coconut red curry sauce.

CocoMaya

A popular, family-friendly bar-restaurant on the beach in Spanish Town, Virgin Gorda, with views of the Sir Francis Drake Channel, the menu melds flavors from southeast Asia and Latin America and features exotic cocktails.

Marina Cay Bar & Grill

Located on a tiny, private island with a sandy beach and mooring ball facilities, this lively bar-restaurant, best-known for its freshly-caught lobster and live reggae, is open for lunch and dinner. 

Bananakeet Cafe

Local couples book this casual restaurant high up in the lush hills of Tortola for a romantic dinner with sunset views over Jost Van Dyke, Great Thatch and Great Tobago.

Don’t Miss 

The Baths National Park 

At the southwestern tip of Virgin Gorda, follow a one-way trail that winds through leafy forest and towering granite boulders, ending at a sandy beach. 

Virgin Gorda tour

Book driver Toots, who will take you on a tour of Virgin Gorda, featuring stops at Savannah Bay and Hog Heaven, which looks out over islands including Anegada, Necker and Moskito, the latter two owned by Richard Branson.