Island Hopping in the British Virgin Islands: A Seven Day Sojourn by Catamaran

Looking for an unforgettable tropical escape packed with adventure, white-sand beaches, vibrant beach bars, fresh seafood, world-class snorkeling, and sunsets that melt into turquoise waters? Welcome to the British Virgin Islands (BVI). This stunning British territory—home to over 50 islands and cays including Tortola, Virgin Gorda, Anegada, and Jost Van Dyke—offers the ultimate destination for travelers seeking fun and festivity, as well as rest and relaxation.

While some travelers prefer to stay at a posh resort, my husband and I, along with two other couples from Koa Kai Marina in San Diego, opted to explore the BVI aboard a private power catamaran charter from The Moorings. The company offers over 300 sail and powercats ranging in size from 40’ to 53’. Our floating home for the week? A Moorings 534 powercat. Enjoy a tour of this magnificent vessel in The Moorings video below!

Arrival in Tortola – Getting Ready to Cruise

After a red-eye flight from Phoenix to Miami, a layover, and a short hop to Tortola, we were greeted by the warm Caribbean air and The Moorings’ professional team. While our yacht was being prepped, we enjoyed lunch nearby then stocked up on provisions at the local market and liquor store.

That afternoon, the designated captains in our group attended a thorough charter briefing—covering safety, mooring procedures, navigation tips, and island-specific advice (including what to do in case of sea urchin pricks, jellyfish stings, or coral cuts). We boarded Seafit at 4 PM for our sleep-aboard night, a great option for those wanting to settle in early.

Seafit was a dream. At 53’ long and 25’ wide, this power cat felt like a luxurious floating villa, with four spacious staterooms, ensuite heads, a fully equipped galley, a plush salon, ample outdoor lounging space, an upper deck with grill and fridge, optional WiFi, and even a water maker, which converts salt water to fresh water for showers and dishes.

After storing provisions, we toasted the start of our journey with handcrafted margaritas on deck and dined at Charlie’s, the on-site marina restaurant, reveling in anticipation of the island adventures ahead.

Jost Van Dyke – Painkillers, Pools, and Party Vibes

After a short morning weather delay, we left The Moorings marina and cruised to Jost Van Dyke, the most relaxed and legendary island in the BVI. Our first stop was Diamond Cay, where we moored and took the dinghy to Foxy’s Taboo for our inaugural Caribbean cocktail—the renowned Painkiller.

Back aboard, we cruised around to Great Harbor and scored a mooring ball before taking the dinghy to the famous Soggy Dollar Bar in White Bay, famous for the original Painkiller recipe. We lounged on beach chairs with our feet in the surf, then walked next door to Hendo’s Hideout to enjoy another Painkiller and conch fritters—my favorite island snack. Conch fritters are made from the meat of conch shells, mixed with Caribbean spices, then battered and deep fried like hushpuppies.

That evening, we dined on Rum Ribs and fresh fish at The Tipsy Shark , then danced late into the night at nearby Foxy’s, a legendary beach bar known for its lively music and spontaneous fun.

 Virgin Gorda – Celebrity Hotspot and Saba Rock Splendor

After sleeping in and enjoying homemade breakfast burritos on board, we made our way to Virgin Gorda, cruising past Necker Island (owned by Sir Richard Branson). We docked at the renowned Bitter End Yacht Club, a marina resort perfect for relaxing after a night on the hook.

Snorkeling, cocktails on the beach, and chilling in swaying hammocks made for a perfect afternoon. Later, we dinghied to Saba Rock, a tiny island with a big reputation. The resort has been beautifully rebuilt post-Hurricane Irma and features nightly tarpon feeding—a mesmerizing sight!

Dinner at Saba Rock was divine. Afterwards, the upstairs bar came alive with DJ music and dancing. We even ran into a fellow group of boaters following the same itinerary. Connections like these are one of the many joys of charter life.

Exploring The Baths & Pirate Fun at Leverick Bay

In the morning, we headed to Leverick Bay for a slip at the marina and took a lively open-air taxi to The Baths — a must-see natural wonder. Giant granite boulders create hidden pools, sunlit grottos, and winding trails that feel like something out of a fantasy novel.

After our hike and a cool-down at Top of The Baths - which includes a restaurant, bar, and refreshing pool, we returned to Seafit to rest up before a night of entertainment on the beach at Leverick Bay.

That evening, we joined the crowd at Michael Bean’s Happy Arrrr Show—a pirate-themed musical performance full of island songs, conch-blowing contests, and lots of laughter. We closed out the night with dinner and cocktails on deck, as we watched the sunset paint the sky in oranges and gold.

Oil Nut Bay Luxury and Dinner at Cocoa Maya

After a restful night at Leverick Bay, we cruised a short distance to Oil Nut Bay, a resort on Virgin Gorda reachable only by boat or helicopter. This upscale destination offers stunning snorkel spots, a serene beach club, an infinity pool, and luxurious tranquility.

In the evening, we boarded a water shuttle for dinner at Cocoa Maya, one of the most romantic restaurants in the BVI. Nestled right on the sand with candlelit tables, craft cocktails, and unbeatable views of the sunset, this was a highlight of the trip. The whole fried red snapper was exquisite, and the ambiance was pure Caribbean magic.

Anegada – Beach Bars, Flamingos, & Lucious Lobster

Our early departure led us to Anegada, the only coral island in the BVI chain. Flat, remote, and encircled by the sprawling Horseshoe Reef, it feels like another world.

After mooring, we went ashore to rent mini mokes, which are fun open-air cars, and explored the island, spotting Caribbean flamingos, goats grazing roadside, and sparkling pristine beaches. We bar-hopped from Big Bamboo to Cow Wreck to Tipsy’s, sampling lobster fritters and, of course, more Painkillers.

Dinner was reserved at Sid’s Pomato Point, known for the freshest lobster in the BVI. Each plate came with two enormous tails—succulent, sweet, and grilled to perfection. We lingered with cocktails, meeting Sid, the owner, before heading back to the boat under a sky full of stars.

Stormy Seas and Norman Island Shenanigans

This was our longest leg—around 3 hours—and Mother Nature had a surprise in store for us. We knew some rain was passing through our path but soon found ourselves facing 4–6 foot swells and heavy sheets of rain with minimal visibility. Thanks to the teamwork of our experienced crew, we made it safely to Norman Island in time for lunch.

After mooring, we made a beeline for Willy T’s, a floating pirate ship bar and restaurant, infamous for its wild atmosphere and daring guests who leap from the top deck 20 feet into the sea. Of course, I had to join them! It’s a popular respite for fun, comradery, and a bit of good old pirate debauchery.

Dinner this evening was at Pirate’s Bight on Norman Island, beautifully rebuilt after Hurricane Irma. While the ambiance was great, this was our only disappointing meal—mediocre food and slow service. Still, the laughter and stories at our table made the night quite memorable.

Peter Island Paradise and Return to Tortola

Our final day included a visit to Peter Island, a luxurious private resort that epitomizes tranquility. With access to exclusive beaches, a beautiful pool, a world-class spa, pickleball and bocce courts, and dreamy hammock-filled gardens, this was the perfect place to unwind before heading home the next day.

After one last morning trip across the sea, and a final mimosa toast aboard Seafit, we returned to The Moorings marina on Tortola. Packing up was bittersweet—but we left filled with gratitude, friendship, and sun-kissed memories that will last a lifetime.

Trade Your Desk Chair For a Captain’s Chair: Charter a Boat in the BVI

Whether you’re an experienced boater or a first-time charter guest, a Moorings power catamaran offers a luxurious, customized way to explore the BVI.

The Moorings power and sailboat charters are open to everyone with a passion to learn and a yearning to take on the adventure of cruising the Caribbean Sea.

Each island offers something unique for everyone - from lobster feasts and DJ dance parties to secret coves, pirate legends, and barefoot sunset walks. It is the perfect blend of ocean adventure, island relaxation, and tropical indulgence.

The Moorings 534 Power Cat Seafit

Plan Your BVI Yacht Charter Adventure

• Best Time to Visit: December–May for dry weather and cooler trade winds

• Charter Base: The Moorings Marina, Tortola

• Must-Pack Items: Reef-safe sunscreen, water shoes, dry bag, camera, binoculars, swimsuits, sunglasses, layered shirts. If your hometown has stickers, be sure to bring them to commemorate your visit on a wall at each beach bar!

• Local Favorites: Painkillers, conch fritters, lobster, fresh fish, and Bushwackers

• Shopping: Each island has an array of fun and fabulous logo’d merchandise and tropical apparel for sale. Save room in your suitcase to bring home a collection of memories!

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Join me on my next voyage aboard NCL’s Jewel as I return to one of my favorite islands, Bermuda.

I’ll spend some time in Boston before embarkation, discovering one of the historic city’s most creative communities.

Till then, keep cruisin’ through life, discovering your own special Things!

CHEERS!