Meet Arabella at Soper’s Hole

Most guests begin their adventure by flying into St. Thomas which has direct flights from the NYC area. Then you hop on a 45-minute ferry ride directly to the West End of Tortola. This is a small, friendly customs port, so you’ll clear entry quickly and easily. From there, you can stop by Pussers for a Pain Killer and get picked up by our tender which will whisk you across the turquoise water to your home for the week—Arabella, anchored gracefully in one of the most beautiful harbors in the Caribbean. If you prefer to fly directly to Tortola’s Beef Island Airport (EIS), simply take a taxi across the island to the West End to meet the tender and begin your unforgettable voyage.

Cooper Island & Marina Cay

Mid-day, we’ll pause at Cooper Island for a leisurely lunch by the sea. The Cooper Island Beach Club is a true culinary highlight — from fresh, local seafood and bold island-inspired flavors to handcrafted cocktails, solar-powered craft beers, and a relaxed, open-air dining vibe right on the sand. After lunch, we’ll set sail toward Marina Cay, where we’ll anchor for the evening and choose among dining ashore or aboard.

Marina Cay itself is a charming, intimate island just off Scrub Island, offering a cozy Bar & Grill atmosphere under the stars. Their menu features island classics and shareables — think tropical seafood, ceviche, burgers, and flavorsome cocktails that pair perfectly with sunset views. Walk to the top of Marina Cay just at sunset to see the magical lure of this quaint island.

North Sound & The Bitter End

Sail into the stunning North Sound of Virgin Gorda, a sailor’s paradise surrounded by turquoise waters and island charm. Drop anchor at the iconic Bitter End Yacht Club, recently rebuilt and better than ever, where you can enjoy a waterfront lunch, explore boutiques, or sip cocktails with fellow sailors. Just across the channel, Saba Rock offers a lively after-hours scene — grab a seat for their famous sunset fish feeding, then stay for music, rum drinks, and the best nighttime vibe in the BVI.

Anegada

If the weather is fair, we’ll make the unforgettable sail to Anegada, the BVI’s only coral island — a low, shimmering atoll surrounded by brilliant turquoise shallows. Unlike the other mountainous islands, Anegada feels like another world, with endless white-sand beaches and a wonderfully laid-back vibe. We’ll spend the afternoon at Cow Wreck Bay, a legendary beach bar where the water is impossibly blue, the music is mellow, and time seems to slow down. As the sun sets, prepare for one of the Caribbean’s most celebrated meals — a fresh-caught Anegada lobster dinner, grilled on the beach under the stars, perfectly paired with island cocktails and good company.

If the weather or swell makes Anegada unreachable, our alternative is the elegant Peter Island Resort, where guests can enjoy a peaceful anchorage, indulge in treatments at the island’s renowned spa, and dine overlooking one of the most picturesque bays in the British Virgin Islands. Whether it’s Anegada’s barefoot charm or Peter Island’s quiet luxury, this day always becomes one of the voyage’s most memorable highlights.

Jost Van Dyke & White Bay

A visit to White Bay on Jost Van Dyke is pure Caribbean bliss. Spend the afternoon barefoot on the powdery white sand, floating in the crystal-clear shallows with a frosty Painkiller from the world-famous Soggy Dollar Bar in hand. The scene is lively but relaxed — beach music, laughter, and sailboats bobbing just offshore. As the sun dips low, we’ll weigh anchor and make our way around to Great Harbour, where the night begins at Foxy’s, the legendary beach bar known for its live music, island barbecue, and irresistible energy. Whether you dance under the palm trees or enjoy a laid-back dinner ashore, Jost Van Dyke always delivers a great Caribbean night.

Norman Island

Our final anchorage brings us to The Bight at Norman Island, one of the most storied harbors in the Caribbean and said to be the inspiration for Treasure Island. Drop anchor in the calm, turquoise bay and spend the afternoon swimming or taking the scenic hike up the hill for breathtaking views across the Sir Francis Drake Channel. Ashore, enjoy margaritas and island fare at the laid-back Pirate’s Bight beach bar — a perfect spot to unwind in the sun. As evening falls, the energy shifts seaward toward the famous Willy T, a floating bar and restaurant known for its lively parties and unforgettable nights under the stars. Whether you’re relaxing on deck or joining the fun, a night at Norman Island is the perfect finale to a week of adventure aboard Arabella.

The Royal BVI & the West End Yacht Clubs

One of the great joys of joining the Manhattan Yacht Club flotilla in the BVI is the lively camaraderie that fills every evening. There’s always a party somewhere — whether it’s cocktails on deck, music ashore, or dancing under the stars. Along the way, we’re joined by fellow sailors from the Royal BVI Yacht Club and the ever-spirited “loyal” West End Yacht Club, creating instant friendships across islands and burgee lines. On Saturday morning, all three clubs come together for a friendly regatta, blending fun competition with island adventure. That evening, we’re invited to their yacht club for dinner and a trophy celebration, where laughter, stories, and toasts continue long into the night — the perfect finale to a week of sailing paradise.