The British Virgin Islands: Explore The Sailing Capital Of The Caribbean

Having lost her dad to cancer three years ago, Camilla Hewitt sets sail across the British Virgin Islands to live out the Caribbean yachting trip of his dreams.

Your Guide To The British Virgin Islands

Cooper Island

If you’ve ever been to the Caribbean, you’ll know that for every beach bar serving frozen cocktails, there’s a slogan T-shirt waiting to be bought, proof that you really have ‘been there, done that, got the T-shirt’. My dad took this saying seriously, spending every holiday collecting them, his wardrobe proudly announcing to anyone he met that he was permanently ‘On Island Time’. I lost him to cancer three years ago, and travelling to the British Virgin Islands felt like a way to revisit the trips we once took together, perhaps with a slight upgrade in accommodation. 

As a family, we island-hopped through the Abacos in the Bahamas, spending most days exploring the coral reefs and meeting their kaleidoscopic residents. The BVI feel similar in that respect; each new island provides another opportunity to spot parrotfish, stingrays, and hawksbill turtles. The child in me felt the familiar urge to buy one of those laminated fish identification cards, just so I could report back to Dad exactly what I’d seen. Compared to the vast archipelago of the Bahamas, the British Virgin Islands are far more compact, made up of around 60 islands, 16 of which are inhabited. Short passages between the hilly silhouettes mean calm, sheltered sailing. I remember navigating the low-lying Abacos with Dad, eyes glued to the depth finder as we crept through the shallow waters. In contrast, the BVI coves feel more forgiving, and even the quietest bays are equipped with mooring buoys. With such a well-established yachting culture, the popular anchorages around Jost Van Dyke and Virgin Gorda are rarely empty, so it’s best to claim your spot early.

BEYC Sailing

We were being shown all the BVI has to offer by Horizon Yacht Charters, who are based in Nanny Cay on the island of Tortola. With a fleet of monohulls and catamarans, Horizon operates a range of barefoot, captained, luxury crewed and learn-to-sail charters. On our first day, a gentle hour-long sail brought us to Norman Island, where we took the tender ashore for lunch at Pirates Bight. True to most Caribbean beachside restaurants, the menu featured conch fritters, coconut shrimp, jerk chicken and mahi-mahi burgers, all washed down with rum-laced daiquiris. After lunch, we motored over to Willy T’s, the legendary floating barge once known for handing out free T-shirts to anyone brave enough to leap from the top deck. Word spread quickly though, and when faced with crowds like my T-shirt-enthusiast dad, the deal disappeared. 

Later that afternoon, we made our way to the northwest shore of Cooper Island for dinner at the Beach Club, a family-owned eco-resort with eight beachfront rooms and an elevated restaurant offering one of the best menus in the BVI. Lobster season had just begun, and with eyes bigger than my belly, I ordered enough to feed two. As we headed to our berths for the night, we agreed on an early start so we could reach Little Harbour on Peter Island, a lesser-known anchorage that offered our best chance of spotting turtles. For me, this was the highlight of the trip, perhaps because my dad’s name was Peter and it felt serendipitous to spend the morning there, or perhaps because of the turtles themselves, who seemed blissfully unaware of our company as they grazed on the seagrass below. I happened to be reading God Is An Octopus by Ben Goldsmith, a beautiful reflection on loss and finding solace in nature, and that morning a line from the book felt perfectly timed: ‘If you sit quietly anywhere, it doesn’t take long for wildlife to become comfortable enough in your presence to resume their usual bustle round you.’

Bitter End Yacht Club

That afternoon, we made our longest crossing, heading for White Bay beach on Jost Van Dyke, home of the Soggy Dollar Bar and its famously potent Painkillers – a delicious blend of dark rum, cream of coconut, pineapple, and orange juice, finished with freshly grated Grenadian nutmeg. It felt like the right place to buy a T-shirt in honour of my dad. ‘A Sunny Place For Shady People’, it reads, and I’m sure he would have approved. Relaxed by a few Painkillers, we made our way to a floating spa anchored off Jost Van Dyke. Built from lumber salvaged across the BVI after Hurricane Irma, the Ocean Spa offers massages aboard a glass-bottom barge, where you can watch the water drift by beneath you. That evening, we joined the BBQ at Foxy’s, a characterful bar adorned with flags, caps, T-shirts, and stickers left by visitors since it first opened in 1968. It’s easy to dance your way into the early hours here, but with one more full day of sailing ahead, we decided to keep our heads clear.

At dawn, we enjoyed another breakfast on board, watching the sun rise from the deck. We then picked up a mooring buoy at Monkey Point, located on the southern tip of Guana Island. This protected spot is known for its calm, clear waters, and we were soon joined by other groups snorkelling around the rocky outcrops. Even as an adult, I’m captivated by the busy world beneath the surface: schools of blue tang darting about, unbothered parrotfish grazing calmly, quick flashes of eyes disappearing into crevices before I can see who they belong to, and coral fans swaying with the current. I could happily spend hours watching these underwater scenes unfold.

Bitter End

From Guana, we set sail on our final passage to the Bitter End Yacht Club on the eastern end of Virgin Gorda, a route that offers views of Richard Branson’s Necker and Mosquito Islands. Stretching along a mile of beach and waterfront, the Bitter End looks out over the sheltered waters of North Sound. Its prime position has made it a popular outpost for watersports enthusiasts, offering ideal conditions for sailing, diving, and foiling. Rebuilt gradually after Hurricane Irma, Bitter End now features over-water accommodation in two-storey timber-clad Marina Lofts and a four-bedroom Marina House, as well as airy Beach Bungalows that open directly onto soft white sand. In an effort to revive the resort’s vintage nautical charm, materials have mostly been upcycled, with massive amounts of hurricane debris incorporated into the new buildings. That evening, after a rum tasting in The Quarterdeck bar and dinner at The Clubhouse restaurant, we turned in for the night, no longer rocked to sleep by the gentle sway of the boat, but drifting off all the same.

On our final morning, we took the short ferry to Gun Creek and drove to The Baths National Park. Not to be missed, this natural geological wonder features enormous granite boulders that form a maze of caverns and rock pools that fill with the turquoise waters of Devil’s Bay. After lunch at Saba Rock, a nine-room private-island resort just a stone’s throw from the Bitter End, I spent the rest of the afternoon on the beach, letting the emotions of the trip settle in. It felt as if I’d been spending time with my dad, doing what he loved and, inherently, what I loved. Along the way, I’d heard stories of how residents rebuilt the British Virgin Islands after the devastation of Hurricane Irma, and a passage from God Is an Octopus seemed to echo both their journey and my own through loss and grief:

To every thing there is a season, and a time to every purpose under the heaven:

A time to be born, and a time to die; a time to plant, and a time to pluck up that which is planted;

A time to kill, and a time to heal; a time to break down, and a time to build up;

A time to weep, and a time to laugh; a time to mourn, and a time to dance; 

ECCLESIASTES 3:1-4

Starting rate for a 6-cabin Lagoon 51 2025 catamaran in the Horizon BVI fleet is $2,599 per day (low season). horizonyachtcharters.com. Nightly rates for Bitter End Yacht Club starting from $650 (low season).