BVI Flotilla: Boats, Beaches, Buddies & Beyond

My mother swears a perfect vacation requires three Bs: “books, booze, and my butt on a beach!” The British Virgin Islands certainly delivered on those, however, our 2026 BoatU.S. Member Flotilla with The Moorings in early June added a few more ingredients to my mom’s recipe: boats, breathtaking scenery, beach bars, a boatload of new buddies, and one-on-one time with the star of Bravo’s “Below Deck Sailing Yacht,” Capt. Glenn Shephard. The result was seven magnificent days of cruising aboard luxurious powercats, exploring hidden coves and colorful harbors, sharing great meals and so many laughs, and discovering why this compact archipelago in the northeastern Caribbean remains one of the world’s most beloved charter destinations.

The Boats

Our glorious week started at The Moorings base in Road Town, Tortola, where we welcomed 24 BoatU.S. members joining us for a tropical adventure. The base was a hive of excitement with guests checking in, provisioning underway at the market on base, and our skippers being briefed on the ins and outs of BVI cruising.

After dropping our bags aboard Sea Señora, our floating home for the next seven days, the trip suddenly felt real. My boyfriend, Griff, and I soon met the rest of our crew aboard our lead boat: Tina Huewe, The Moorings marketing manager; Marlon, our experienced captain from The Moorings; and, of course, Capt. Glenn, whom everyone wanted to meet.

Our 46-foot Leopard catamaran was spacious enough that the five of us never felt cramped, yet intimate enough that we’d quickly learn each other’s routines over breakfast egg-and-cheese sandwiches and evening sundowners. Like the other boats on the flotilla, ours was equipped with everything needed for a week of island hopping – from comfortable cabins with private heads to a well-equipped galley, generous outdoor living spaces, and plenty of room to gather under the shade of the hardtop after a day on the water.

Even for those of us accustomed to our own boats, there’s something uniquely liberating about chartering. Once our bags were unpacked and we’d stowed our provisions, all that remained was to cast off and explore in the company of others.

Beauty

The BVI seem almost purpose-built for cruising. More than 50 islands and cays lie close enough together that often we could see tomorrow’s destination from today’s anchorage. Short passages and easy line-of-sight navigation allowed us to enjoy breakfast in one bay, snorkel over coral reefs by midday, and be tied to a mooring ball with a Painkiller in hand before sunset.

Cruising here isn’t about making miles, however; it’s about discovering anchorages, each with its own personality – from towering granite boulders and hidden sea caves to palm-lined beaches and lively waterfront beach bars. Nearly every stop invited us into the water, whether to snorkel among colorful reef fish, watch sea turtles swim leisurely by, or simply float in water so clear we could see bottom. Somehow every dinghy trip ashore turned into another memorable afternoon.

Beaches

BVI beaches aren’t necessarily bigger or flashier than elsewhere in the Caribbean, but each is distinct. Norman Island’s rocky shoreline, dramatic cliffs, and hidden sea caves lend it a wild and mysterious feel, while the expansive powder-white sands of Anegada’s Loblolly Bay and Cow Wreck Beach seem to stretch endlessly into turquoise shallows. On Virgin Gorda, The Baths offers a landscape unlike almost anywhere else in the world, where house-sized granite boulders form winding passages, hidden pools, and pockets of white sand sculpted by centuries of wind and waves. Together, these beaches created a coastline that we breathed in one anchorage, one dinghy ride, and one barefoot stroll at a time.

Bars, Brews & Bites

Wherever there are beaches in the BVI, you’re likely to find a beach bar. Many are a short dinghy ride from the mooring field, and it’s common to arrive barefoot, tie up at the dock, and sidle up to the bar to people-watch or swap sea stories with fellow flotilla members and cruisers over fruity beverages or cold local lagers.

The islands’ signature cocktail, the Painkiller, was invented at the Soggy Dollar Bar on Jost Van Dyke but is served everywhere throughout the BVI. If yours doesn’t come topped with a generous dusting of freshly grated nutmeg, you may want to find another bartender. Just a short distance away, Foxy’s in Great Harbour has been welcoming sunburned sailors since 1968. As the sun sets, the music gets louder and the dance floor fills. And, if you’re lucky, as we were, you might even meet “Foxy” Callwood himself, dispensing his trademark island wisdom.

One of the most iconic stops is Willy T, a converted steel-hulled cargo ship anchored in The Bight off Norman Island. The floating bar serves drinks, casual fare, and a healthy dose of entertainment. For the adventurous (including some of our flotilla members as well as Griff and me), the unofficial rite of passage involves climbing to the upper deck and leaping into the clear Caribbean water below.

While most charterers carefully provision before casting off, we greatly overestimated how many meals we’d eat aboard. Waterfront restaurants are plentiful, making it tempting to trade the galley for fresh seafood, Caribbean specialties, and sunset dinners ashore. Look around while you’re there and you’ll notice another BVI tradition: walls, ceilings, and rafters decorated with mementos left behind by visiting boaters. Items included custom boat and business stickers, burgees, T-shirts, hats, license plates, and handwritten notes. Our group left our mementos, too, alongside thousands of other cruisers.

‘Below Deck Sailing Yacht’

Capt. Glenn Shephard

Full disclosure: I didn’t know too much about Glenn Shephard or his show on Bravo before stepping aboard Sea Señora. His many fans, among them BoatU.S.’ marketing manager, my mother, and several close friends and colleagues, assured me he was a super-friendly guy on his show. They were right.

A brand ambassador for The Moorings, Glenn joined the flotilla to spend time with BoatU.S. members and enjoy a little vacation of his own. Wherever we went, someone recognized him, and he never tired of chatting – about his popular show, boats, cruising, or posing for photos. He had a knack for making every conversation feel unhurried, giving each person his full attention.

His enthusiasm for boating is genuine, whether talking about sailing his own boat in the Mediterranean or geeking out over the latest marine gear and technology. He spent plenty of one-on-one time with our members, answering questions, telling stories, talking boats, and musing about future cruising plans.

While underway, Glenn happily left most of the helm duties to our Moorings captain, Marlon, stepping in to help with anchoring when needed. He was always right there rolling up his sleeves to help wash dishes – a gesture that perfectly reflected the kind, unassuming person his fans already knew him to be.

Buddies

Often, one of the best parts of a flotilla is the people. We were all so different, yet we started with key things in common: a love of boating and a sense of fun and adventure. The evening before departure we gathered at a welcome reception at The Moorings base, where everyone received a commemorative swag tote filled with goodies from BoatU.S. and The Moorings, as well as custom BoatU.S. Flotilla sun shirts we’d wear throughout the week. Tina and I welcomed the group and introduced Capt. Glenn, whose participation was one of the main reasons several members had excitedly signed up for the trip.

From there, friendships formed quickly. Our WhatsApp Flotilla Fun group chat buzzed throughout the week with photos, tips, and plenty of good-natured banter – and continued even after we’d all returned home. We gathered for dinners and at beach bars, cheered each other on during a boat-versus-boat giant Jenga championship, and danced the night away at Leverick Bay and Foxy’s.

Every great boating trip generates its share of stories. A couple dinghies untied themselves and – fire drill! – had to be rounded up and returned. One crew accidentally ran over a BuoyBall, wrapping the line around their prop. Thanks to Marlon’s connections, it only cost them lunch ashore to get it untangled by a diver. Another crew discovered a squatter still tied to their assigned mooring ball, prompting Capt. Glenn to step in and smooth things over. Everything ended happily, and we moored alongside them several more times during the week. By the end of the trip, they’d become part of our extended flotilla family.

These moments and many more all became part of our shared adventure, making the stories we still tell and laugh about. We arrived as strangers brought together by a flotilla, but we left as friends who helped each other, played together, and exchanged contact info, many already talking about doing it all again next year.