Explore the British Virgin Islands Via an Upscale Yacht Charter

Choose your own British Virgin Islands adventure and indulge in all the best of a Caribbean getaway — without the crowds — on a bespoke yacht.

Would-be island hoppers are often left to choose between two less-than-thrilling options: Take a crowded commercial cruise or plan a complicated DIY vacation that makes you want to bury your head in the sand. Even the fantasy of escaping to the British Virgin Islands — arguably the most beautiful locale in the Caribbean — can be ruined by the thought of endless logistics, mediocre food, or a fixed schedule with no escape.

“It may change how you vacation forever.”

Thankfully, there is another way to indulge in the aquamarine waters, dazzling harbors, and white-sand beaches of the British Virgin Islands (BVI) — and it may change how you vacation forever. In recent years, the rise of be-spoke yacht charters has offered sun-seekers a more intimate, flexible, and accessible way to vacation, allowing travelers to tailor their destinations, activities, dining options, and company to their exact preferences.

The Moorings is an upscale yacht charter company with a fleet of more than 400 vessels across nearly two dozen destinations around the globe, including a new service to La Paz, Mexico, that launched in December 2024. But the company truly hangs its captain’s hat in BVI, where it has operated since 1969 and more than half its vessels are based. If the idea of packing your family up for a vacation that involves a lot of screaming and hauling beach chairs sounds less than appealing, let the freeing relaxation of a five-day BVI escape on a private, 10-person catamaran melt those fears away. And there is zero beach-carting or amusement park line-waiting involved.

- Advertisement -

beach

Getting Started

For Westchester travelers, JFK Airport remains the best hub for direct flights to St. Thomas, which is the easiest connection point for BVI. An early morning flight guarantees an extra day of sailing, so consider starting your vacation overnight at The TWA Hotel. Since opening in 2019, the retro-themed hotel in a former TWA flight center has won the elusive approval of aviation nerds, design fans, and 1960s obsessives alike.

While a rooftop pool, the world’s largest hotel gym, and a variety of onsite dining from Mister Softee to the Paris Café by Jean-Georges to Connie, a 60-year-old plane outfitted with a vintage cocktail bar, will win many plaudits, the hotel’s biggest style point may be its location. The TWA Hotel sits on the grounds of JFK, just a few feet from the terminals. After watching planes take off from your hotel bed, nothing may be more gratifying than avoiding the stress and chaos of a morning airport run by simply walking to your flight as the pilots do.
yacht

Arrival

After the four-hour flight, most of your work to get onto the open ocean is complete. Once you arrive in St. Thomas, a taxi whisks you to Red Hook on the island’s east end, where you board a private, high-speed water taxi to The Moorings marina.

By the unhurried standards of the islands, it is an efficient ride, aided by a cooler of seltzers, a steady breeze, and local Carib beer. Just get your passport checked and you’ve officially made it to BVI.

- Partner Content -

On Board

Upon arrival at The Moorings marina, your chariot — aka catamaran or monohull — awaits. In our case, it was a 58-foot vessel named the Laurel Lee, outfitted with six cabins. Each room had its own bathroom and shower and, crucially, air conditioning, which makes it easy to retreat in comfort no matter the time of year.

Ample seating and covered lounging spaces on the stern, deck, and behind the elevated cockpit make for collegial gatherings, group meals, and easy lookout points for giant turtles and sweeping sunsets. The vessel can easily transition from motor power to sail when a slower pace of life appeals and, no matter what the speed, a Bluetooth-enabled stereo system allows for plenty of yacht rock.

Dining

For many seafaring vacationers, the biggest worry about sailing isn’t calm waters, but rather, calm stomachs. But fear not: The Moorings crew personalizes its onboard offerings for meals, cocktails, and snacks based on an in-depth survey each passenger fills out weeks before setting sail. The survey goes far beyond food allergies, covering everything from preferred cuisines to portion sizes to favorite wines, beer, and spirits. The Moorings staff then loads up the larder for every occasion, from grand dinners to packaged snacks.

What the company profoundly undersells is how good the eating will be. Up against the beach burger shacks and the precious portions of island resorts, Chef Kay, our trained onboard gourmand, carefully works around all lifestyles and allergies to create sophisticated, balanced, and satisfying meals for every passenger to enjoy after long days in the sun. French toast, omelets, and fruit plates help to greet the day while whipped-up snacks like bruschetta and crudité appear after off-boat excursions. Ahi tuna, seafood pasta, jerk chicken, and burgers fortified the group before the short swims to shore or nights out at the beach bars. No gourmet detail is overlooked — even the breads and pastries are baked fresh on the Laurel Lee while guests go ashore or enjoy a dive off the boat.
yacht dock

“No gourmet detail is overlooked.”

Perhaps more importantly, for those on a friends’ trip or girls’ getaway, the drinks are endless: welcome drinks, breakfast drinks, post-swim drinks, pre-dinner drinks, and wine pairings. Assisting Chef Kay, two other members of the three-person crew stand ready to ferry passengers from destination to destination, or to consult about popular attractions, while also suggesting drink choices from classic island cocktails (don’t pass up the BBC, a banana, Baileys, and coconut cream dream shake) and bloody mary’s to mimosas and Aperol spritzes.

- Advertisement -

Destinations

One of the bigger challenges of the British Virgin Islands — admittedly a terrific dilemma — is deciding between all the destinations and activities at your disposal. But one of the benefits of creating your own BVI adventure through a private yacht charter is the opportunity to balance your choices between must-see natural attractions, island hotspots and institutions, and quiet places where you can indulge in relaxation. Here are some of the many iconic options for a getaway among the islands.

Norman Island

Though the option to spend your first night at The Moorings marina after the flight might appeal to some travelers, a better choice may be to set sail for a nearby outpost in BVI. Norman Island at the southern tip of the BVI archipelago provides a picturesque opening salvo.

Spend a few hours snorkeling through lush coral gardens and train your goggles toward reef fish of all sizes and colors. Or swim toward other-worldly rock formations at the base of the island’s cliffs. Then, back on board, catch your first sunset and dinner before a short ride to William Thornton’s celebrated floating watering hole and grill — aka Willy T — where fist-pumping BVI nightlife pulsates around the barge’s large bars. Between the natural beauty and natural chaos, Norman Island is a perfect capsule of island life.

Anegada

For those seeking a truly remote type of paradise, Anegada beckons. The northernmost island in BVI is as out of the way as it gets. After dropping anchor, you’ll feel like you have the run of the island’s low-key beach bars, restaurants, and hotels.

While some new arrivals tend to light out for Anegada’s walking trails, secluded beaches, jaw-dropping lookout points — or its Instagram-worthy flamingo pond — just opt for a pina colada under the thatched palapas of the Anegada Beach Club, a handsome, unassuming resort on the island’s north end. As the afternoon slowly drifts toward dusk, a secluded white coral sand beach behind the club awaits. Take a local’s advice: Reserve a dinner spot at the Anegada Reef Hotel, which hosts a lavish lobster feast on the beach.

Virgin Gorda

Seemingly no trip to BVI is complete without a pilgrimage to The Baths, part of the iconic Virgin Gorda National Park, where a unique outlay of dramatic boulders, caves, and rock pools waits to be conquered (even by the most barefoot of casual visitors).

The Baths are just one draw of the island of Virgin Gorda, which has an abundance of harbors, properties, water sports, and attractions vying for attention. The marina at Leverick Bay offers a low-key resort, bar, and a family-friendly barbecue buffet, along with live music and performances by Moko Jumbies — lavishly costumed stilt walkers and fire dancers. Meanwhile, just across the bay, the bustling scene at the sleek, shiny Bitter End Yacht Club is Southamp-ton-meets-South-Beach and the exclusive resort at nearby Saba Rock continues to attract masters of both the kiteboard and the boardroom.

ocean
For The Moorings 46.3 – 3-cabin monohull, pricing starts at $4,304 for four passengers staying five nights.

Jost Van Dyke

Even before dropping anchor at Jost Van Dyke, it’s easy to realize you’re on your way to someplace so special it feels forbidden. From the east, yachts of all sizes drift past Sandy Cay, an idyllic nature preserve (formerly belonging to a Rockefeller) that plays host to onshore fauna explorers. From the water, you’ll pass Sandy Spit, a sunbathers’ tiny oasis made famous (and rightly so) by a series of Corona commercials; consider your beach officially found.

Although many travelers visit BVI’s smallest island for its sheltered harbors, postcard vibes, and bottlenose dolphin sightings, the highlight of Jost Van Dyke may be its party spots. Shaded under a tamarind tree, Foxy’s Bar is a legendary haunt among the many casual dives and cafés of Great Harbour — while in nearby White Bay, visitors flock to the Soggy Dollar Bar, where the classic Painkiller cocktail bar was invented (or so they say). The scene is festive and carefree — a Jimmy Buffett song come to life — as it should be on a drop of sand surrounded by crystal-blue water.

Tortola

If the sunbathing is getting to you and you need a break from the beach scene, Tortola is a short sail away from its neighbor Jost Van Dyke. While the laid-back island certainly holds its own with beach bars and black sand, it also boasts Sage Mountain National Park, the largest park in BVI. A few hours spent among the hiking trails, sweeping vistas, and wild varieties of plants and animals will remind anyone that paradise has plenty of definitions.

After breaking a sweat, Cane Garden Bay on Tortola’s northside offers a variety of hotels, shopping, and quiet beaches away from the chaos of noisier ports. Renting a beach lounger and munching on some conch fritters in the breeze may be in order. Or amble over to the Callwood Rum Distillery and sample some offerings from the Caribbean’s oldest rum maker.

“Consider your beach officially found.”

beach water

No Bad Days

Choosing from the bounty of BVI may feel like an impossible feat until you realize it’s truly difficult to make a mistake in paradise. And that’s what makes a yacht-based island vacation so special when the water or the vibe is just right, or when you’re ready for a change of scenery or a new adventure.

Whether you hunker down in one place or tackle several dozen BVI islands, cays, and outcroppings, the chances are good you won’t regret your decision. The Moorings makes vacationing so smooth you’ll never have to worry about details (someone is always three steps ahead of you with a snack or a snorkel), and with relaxation and family time at full throttle, there is not much left to concern yourself with, other than building precious memories and putting on sunscreen.

Adam Chandler is a journalist and author based in New York. His work has appeared in The New York Times, The Wall Street Journal, The Washington Post, WIRED, Vox, New York Magazine, Esquire, TIME, and elsewhere. Chandler is the author of Drive-Thru Dreams.

Related: 7 Stunning Getaways Worth a Drive Along I-95

Our Best of Westchester Readers' Ballot is open through January 15!

Our Women in Business Awards event is November 21!

Our Best of Business event is October 30!

Our CEOs & Business Leaders Golf Outing is August 5!

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.