The beach at the Rosewood Little Dix Bay hotel on Virgin Gorda

How Virgin Gorda Is Making a Comeback After 2 Devastating Hurricanes — and What's New on the Island

Virgin Gorda has a history of attracting free spirits — and after two catastrophic hurricanes, this visionary thinking is exactly what helped three iconic resorts bounce back.

This is a story that begins with a pioneering charter skipper, a modern-day pirate, and a conservation-minded New York financier. It was the early 1960s, and the British Virgin Islands — a lush strand of 50-odd Caribbean islands, islets, and cays 130 miles east of Puerto Rico — had begun to emerge as a plum destination for sailing and diving. Those pursuits were what drew these men to Virgin Gorda, an eight-square-mile dot of land, where they laid the groundwork for some of the region’s most legendary resorts.

By 1978, a few dozen hotels had popped up throughout the BVI, along with a smattering of bars and restaurants that catered to the hardy sailors renting crew-free vessels in what were the nascent days of the bareboat charter industry. Today, travelers to the BVI can take their pick of accommodations. But three resorts — the Bitter End Yacht Club, Saba Rock, and Rosewood Little Dix Bay — introduced a blueprint for hospitality in the region, ushering the British overseas territory into the era of modern tourism.

Two photos from Virgin Gorda, one showing a man in an outdoor shower, and one showing a woman relaxing in a hammock on the beach
From left: Open-air showers overlook the marina at the Bitter End Yacht Club; a beachside hammock.

Amanda Villarosa

Early last March I traveled to the BVI — a place I adore — for a weeklong stay on Virgin Gorda. My last trip had been in the spring of 2018, just seven months after back-to-back Hurricanes Irma and Maria had pummeled the archipelago, leaving hillsides covered in nothing but gray-brown trunks and branches. But nature fought back, as it tends to do, and through the window of the twin-engine Piper on this latest visit, I could see that the islands below had once again erupted into leafy abundance.

Three resorts — the Bitter End Yacht Club, Saba Rock, and Rosewood Little Dix Bay — introduced a blueprint for hospitality in the region, ushering the British overseas territory into the era of modern tourism.

As the little plane cruised northward, away from St. Thomas, in the U.S. Virgin Islands, I watched the coastline undulate in sweeping curves, forming the secret bights and sheltered anchorages that sailors have cherished since pirates and privateers roamed these waters in the 17th and 18th centuries. On previous trips, I had experienced the magic of these sailing grounds primarily on charter boats, hopping from island to island, sipping Painkiller cocktails, and snorkeling around reefs that spread across the ocean floor in Rorschach-like swaths. For days after disembarking, I would feel the motion of the sea when lying in bed at night, a sensation both nostalgic and unnerving.

But this time, I’d be based on terra firma, spending a couple of days at each of those bellwether resorts. All three had been decimated by the hurricanes, and each had recently reopened following a full-scale rebuild. I’d come to hear their stories and see how their legacies had been carried into the future.

The Bitter End Yacht Club

In the late '60s, Basil Symonette, a renegade yacht captain from St. Thomas, settled with his partner on 30 secluded acres of Virgin Gorda’s North Shore. He built a handful of spartan cottages and a pub that became a hangout for his yachting contemporaries and dubbed it the Bitter End, which, in nautical speak, refers to the end of a boat line that’s tied to the ship. Fittingly, the rustic camp was also the last outpost before the Caribbean met the open waters of the Atlantic Ocean.

I first visited the resort in 2002 on a sailing trip with my husband and a group of friends. By then, the resort’s current owners, the Hokin family, had spent decades transforming Symonette’s ramshackle settlement into the Bitter End Yacht Club, a seaside hamlet with 47 breezy bungalows, a world-renowned sailing school, and a fleet of boats for guests to rent.

Two photos from Virgin Gorda, one showing a man on a floating dock, and one showing a canopied guest bed
From left: A floating dock at the Bitter End; a canopied guest bed at the hotel.

Amanda Villarosa

On our 2018 charter, my family and I motored a dinghy up to the North Sound from nearby Leverick Bay, a cove that, at that time, had the only intact mooring balls in northern Virgin Gorda. Though the entire territory had suffered the hurricanes’ wrath, the North Sound arguably took the worst beating. The sapphire waters, normally full of boats and thrumming with revelry, were deserted. The Bitter End’s waterfront village lay in splintered heaps. The remaining bungalows sagged on the hillside, looking more like Dorothy’s twister-ravaged Kansas farmhouse than the cherished cottages they’d once been.

I spent the bulk of my time doing what one is supposed to do at the Bitter End — messing around in boats.

“It was just totally devastating,” Lauren Hokin recently told me over the phone. She runs the property with her father, Richard, who took the helm in the late '90s. “But my dad and I just said, ‘Okay, this is what it is right now. We can either walk away or we can move forward.’ We’d owned the property for fifty years at that point and it needed some updating, so we thought, well, here’s our opportunity.”

Two photos from Virgin Gorda, one showing a man resting on a dock, and one showing a guest room deck
From left: Cooling off in the North Sound, just off the Bitter End Yacht Club’s main building; a seating area in one of the waterfront accommodations.

Amanda Villarosa

Now, almost five years and a pandemic later, it was clear that the revelry had returned. From Virgin Gorda’s tiny airport, I took a taxi to the snug settlement of Gun Creek, where one of the Bitter End’s rigid inflatable boats waited to dash me across the bay. As we zipped along, I listened to strains of reggae float across the sound on the balmy afternoon breeze. Dozens of sailboats bobbed on shiny new moorings, dinghies zipped to and fro, and kiteboards and Hobie Cats skimmed over the sea, their sails billowing with the islands’ famous trades.

Related: the 25 Best Resorts in the Caribbean, Bermuda, and the Bahamas

The Hokins tailored the first phase of the Bitter End’s resurrection to serve the nautical community that put the property on the map, reviving the village, marina, and mooring field so that boaters could once again enjoy the splendor of the North Shore. Visitors like me, who arrive sans yacht, have the option of bunking in one of two waterside bungalows. This airy pair, modeled after traditional sailmakers’ lofts, sits on the edge of the marina; each has a double-decker terrace that juts out over the Caribbean and swim ladders that drop down into the sea.

I arrived in time to catch Richard and his wife, Wendy, at the tail end of a three-week visit. Richard has mastered the art of the sailor’s yarn, and over a dinner of crispy conch fritters and fragrant chicken roti in the resort’s chic new Clubhouse restaurant, he vividly recounted the Bitter End’s history.

Two photos from Virgin Gorda, one showing waterside cocktails, and one showing nautical ropes hanging on a building
From left: The Bitter End 2.0 cocktail and a rosemary-mezcal negroni; nautical ropes.

Amanda Villarosa

Around the time Symonette set up shop, Richard explained, his parents, Myron and Bernice, began taking regular sailing trips up to the North Sound from their winter base in St. Thomas. The couple befriended the eccentric skipper, and one evening over cocktails Bernice asked if he might sell them a piece of land where they could build a cottage of their own. Symonette upped the ante and offered them the whole place. Three years of rather unorthodox negotiations followed — at one point, Richard said, Symonette wanted to be paid in gold bullion — and in 1973 the Hokins took ownership.

“What we didn’t realize was that the bareboat industry had started up on Tortola,” Richard said of those intervening years. Amateur sailors soon caught wind of the North Shore’s magic and began arriving in droves. But those early rental boats lacked the creature comforts of today’s elegant charter yachts. “The wannabes weren’t accustomed to life aboard a small, crowded yacht,” Richard continued. “They started asking if they could rent a cottage so they could have a shower, sleep in a real bed, and indulge in intimate activities that were uncomfortable in two-foot-wide bunks with shipmates in the same space.” He smiled and said, “I suspect the latter is the principal reason the Bitter End became a resort.”

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In its previous incarnation, the Bitter End offered a robust menu of diversions, including sailing classes, weekly regattas, day trips around the archipelago, and sunset cruises. As the Hokins have rolled out Bitter End 2.0, they’ve curated a collection of Caribbean experiences inspired by those same adventures. I spent the bulk of my time doing what one is supposed to do at the Bitter End — messing around in boats. I ventured out on a paddleboard to snorkel in a mangrove cove and kayaked to Prickly Pear Island, where I lolled on a Gilligan-style beach among hundreds of pink conch shells. One afternoon I took my first-ever sailing lesson with Joe Lund, a watersports instructor, and for an hour we coasted through the sound on a 14-foot Hobie Wave with the sea spraying our faces.

Another morning, I met up with Nick Putman, the Bitter End’s assistant marina and watersports manager, for a snorkeling tour. “There’s just been this overwhelming feeling that, man, it’s so good to be back,” he said as we cruised to the Baths National Park. “It’s taken a long time to get to where we are, and it’s been a struggle, but here we are, doing what we love to do.” He smiled and gestured as the ocean went by in a blur.

We picked up a mooring at Devil’s Bay, a scimitar of alabaster sand. Later Putman and I would investigate the Jurassic warren of saltwater pools and sunlit grottoes that define this geological wonder, but first I wanted to explore the granite metropolis the boulders formed beneath the sea. Hovering on the surface, I watched a school of sergeant majors glide among sea plumes while two parrotfish, polychromatic scales glinting, crunched mouthfuls of coral. In the shallows, three iridescent reef squid with comically large eyes observed my progress before disappearing into the aperture between two rocks.

Going forward, the Hokins plan to develop the Bitter End in a way that has the lightest possible impact on the environment — bottling their own water, installing solar power, and capitalizing on natural ventilation. Three more waterside bungalows will be built in the coming months, along with a collection of timber-frame structures reminiscent of their predecessors. “We really tried to preserve the spirit of the place,” Richard said. “It may look a bit different, but the heart and soul are the same.” 

Two photos from Saba Rock resort, one showing the hotel's bar, and one showing the hotel's red boat used to ferry guests to the island
From left: The small bar on the small island; the Saba Rock ferry.

Amanda Villarosa

Saba Rock

Just 300 feet across the sound from the Bitter End yet a world away in vibe, Saba Rock sits like an oasis in the middle of the sea. The one-acre island curls into itself like a nautilus shell, palm trees fringing its perimeter, ultramarine water in every direction.

My seat on Saba’s little red ferry, which I picked up from the Bitter End, provided an excellent view of the new resort. The two-story structure wraps around the island in a sleek semicircle of storm-proof concrete and honey-colored wood. A dock traces its curve and dinghies bump against it, two deep in spots. I could hear the high-energy thump of Soca music coming from the restaurant where a lively lunch crowd filled the tables ringing the water’s edge. It seemed I’d arrived just in time for the party.

More Trip Ideas: Why a Sailboat Journey Is the Best Way to Explore the British Virgin Islands

That spirit of bacchanalia has been part of Saba’s DNA for decades, originally nurtured by a free-spirited New England expat named Bert Kilbride. He bought Moskito Island, an uninhabited bump of land off the northern coast of Virgin Gorda, built a 12-room dive resort he named Drake’s Anchorage, and spent his days scouring the treacherous reef surrounding Anegada for sunken ships. In 1967, Queen Elizabeth II appointed him Her Majesty’s Receiver of Wreck, tasking him with salvaging maritime debris and cementing his reputation as the “Last Pirate of the Caribbean.”

In 1970, Kilbride moved across North Sound to Saba Rock, which in those days was little more than a windswept volcanic spit covered in dry scrub and organ pipe cactus. He cobbled together a house from stone and driftwood that doubled as headquarters for his new diving venture, Kilbride’s Underwater Tours. For decades afterward curious travelers came calling, intrigued by tales of the treasure hunter who called the rock home.

A guest room at the Rosewood Little Dix Bay resort on Virgin Gorda
A Tree House suite.

Amanda Villarosa

Hurricane Hugo struck in 1989, putting a temporary kibosh on Kilbride’s diving business. To make ends meet, he and his wife, Gayla, converted the space into Pirate’s Pub, hawking burgers and Bushwackers to passing boaters. In true buccaneer spirit, Kilbride greeted guests — who ran the gamut from itinerant old salts to Walter Cronkite — with a blue and yellow parrot on his shoulder and chains adorned with gold coins around his leathery neck. The pub flourished until 1997, when Kilbride sold Saba to a restaurateur from Hawaii who rebuilt the place from the ground up, adding a hotel — and a smidge of refinement — to the island’s brand of debauchery. After Irma, billionaire investor Petr Kellner stepped in, working with Czech architect Petr Kolář to redesign the place.

In each of Saba’s nine guest rooms, sliding doors open to a balcony overlooking the waterscape outside. After unpacking, I walked around the island’s perimeter and then, because that took all of 10 minutes, I did it again. This time I slowed down, spiraling up from the pretty beach to the Sunset Bar and back down again, charmed by the beguiling spaces and nautical design details I encountered along the way. The diminutive island is immensely photogenic, with swings hanging by the upstairs bar, hammocks swaying beneath coconut palms along the water’s edge, and British phone booths that add crimson pops to the endless turquoise panorama.

Whenever I began to feel moored on the island, which in theory I suppose I was, I made my way down a sandy path and dove into the sea.

Had I been on a sailing charter, my visit would likely have been short-lived — a few minutes in the afternoon watching tarpon being fed from the dock, a rum punch or two at sunset, dinner at the waterfront restaurant, then back to the boat to sleep. In the morning we would have dropped our mooring and started the long sail up to Anegada, the traditional stop after an overnight in the North Sound. Instead, my two days at Saba Rock stretched into a miniature retreat. I rolled out my yoga mat on the oceanside pavilion. I had a treatment at the spa that blended massage, essential oils, and a sound bath into an experience so restorative it felt like a hug. One afternoon I lounged in a hammock and counted the sea turtles popping up from the reef for breath. And whenever I began to feel moored on the island, which in theory I suppose I was, I made my way down a sandy path and dove into the sea.

Two photos from Virgin Gorda, one showing The Baths rock formations, and one showing a palm tree on the beach
From left: The Baths National Park, a famous geological formation on Virgin Gorda; a palm tree on the beach at Rosewood Little Dix Bay.

Amanda Villarosa

Rosewood Little Dix Bay

From the water, the conical wooden roofs of Rosewood Little Dix Bay appear to rise from the lush, jasmine-scented foliage like something out of Robinson Crusoe. I presumed the resort was just as Laurance Rockefeller had envisioned it when he sailed into the idyllic half-moon bay in 1958 on board his yacht, the Evening Star. By then, the philanthropist had been on the ecotourism trail for a while, having built resorts like Dorado Beach, in Puerto Rico, that, in his words, aimed to “go to the frontiers of natural beauty and keep them in harmony with the locale.”

On the pier I met my butlers, Altamash Khateeb and Hubert Hall, who whisked me away for a tour. Walther Prokosch, the resort’s original architect, wrote that his goal was to evoke “coconut palms in a strong breeze…storm-tossed, irregular, tropical.” When Irma left the property literally storm-tossed in 2017, Little Dix had been on the cusp of unveiling an 18-month refresh. Although the resort’s open-air Pavilion restaurant, with Prokosch’s zigzag of soaring roofs, had been spared, the damage to the rest of the property was catastrophic.

Two photos from Virgin Gorda, one showing the Rosewood Little Dix Bay bar, and one showing a hand on a palm leaf
From left: The Rum Room bar; a Bismarck palm at Rosewood Little Dix Bay.

From left: Amanda Villarosa; Brian DiDio

“All of the rooms were rebuilt on the original foundations,” Khateeb told me as we looped past the Farm, the resort’s new organic kitchen garden. The reimagined property exudes a sleek, vintage aesthetic that harks back to Rockefeller’s philosophy of keeping the environment intact and the resort itself simple and informal. My suite, a midcentury-style haven with vaulted ceilings and a huge wall fashioned from local stone, sat amid an Eden of frangipani and bougainvillea. Just off the patio, a sandy path snaked beneath a bower of sea grapes to the beach, and as I strolled the tawny crescent I spotted a juvenile black-tipped reef shark cruising the translucent water near my feet.

I rose early each morning, wanting to spend every moment possible absorbing my surroundings. Hall made sure I had milk for my tea, which I brewed in a porcelain pot and sipped on the patio while listening to waves lap the sand. Later, I wandered to the Pavilion for breakfast, where I devoured plates of ambrosial mango and papaya and far too many chocolate croissants. One day, Khateeb arranged for Captain Avery Baptiste to drop me at Little Trunk Bay, a secluded beach not far from the Baths, where I swam and sunbathed for hours, living out a castaway fantasy that included the unlikely additions of a gourmet picnic and a chilled bottle of Moët.

A dining pavilion and terrace at the Rosewood Little Dix Bay hotel on Virgin Gorda
The Pavilion, an alfresco dining area.

Amanda Villarosa

My bed at Little Dix was huge and plush — a far cry from the modest bunks of my boating trips. Still, I did miss the mobility that sailing affords. To remedy that, I booked a day on Midnight Moon, a sleek power boat. As we set off, a brief morning cloudburst left a huge rainbow in its wake. In the distance, the Dogs, three jagged islets known for some of the territory’s best snorkeling, rose from the sea. But the current that morning was a bit too rough. Instead, we headed to a tranquil spot called Diamond Reef, where I spotted a surly barracuda lurking near a jetty carpeted in coral. We spent the rest of the day hitting the BVI highlight reel: Sandy Spit, a miniature cay that was almost washed away by the hurricanes; dreamy White Bay, on Jost Van Dyke, home to the famed Soggy Dollar Bar and a chic new hotel, the Hideout; and Norman Island, where I snorkeled near a triptych of caves said be the inspiration for Robert Louis Stevenson’s Treasure Island.

I snorkeled near a triptych of caves said be the inspiration for Robert Louis Stevenson’s Treasure Island.

Later that afternoon, as we approached the southern tip of Virgin Gorda on our way back to Little Dix, I could see the towering boulders of the Baths. I remembered something I’d heard from Elwin Anderson Flax, an 81-year-old lifelong resident who’d given me a history tour earlier in the week. As we wound along the North Sound Road in his pickup truck turned open-air jitney, he shared countless tales of life on the island. The ones that stood out most were his memories of the hurricanes. “That morning after Irma, the whole island was gray,” he said. “And I told myself that for the first time, I was seeing Virgin Gorda as it really is. Naked. And with all that nakedness, the beauty of the rocks."

Now those rocks peeked above the velvety emerald foliage enveloping the hillside. Snorkelers and sailboats filled Devil’s Bay. On the beach, Poor Man’s Bar buzzed with the energy of a happy hour that had started before lunch. Virgin Gorda had risen once again. 

A version of this story first appeared in the December 2022/January 2023 issue of  Travel + Leisure under the headline "Starting Fresh."


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