Ease into your sailing adventure with a comfortable downwind run to The Bight at Norman Island, one of the most secure anchorages in the BVI. The holding is excellent, and the bay offers full protection from the easterly trades — perfect for your first night aboard. Spend the afternoon snorkeling at The Caves or The Indians, then head ashore for dinner or a sunset cocktail at Pirate’s Bight, followed by a night of dancing at the infamous Willy T!
Sail north past Peter Island to Cooper Island, a calm and well-protected anchorage ideal during breezy conditions. Moor early to enjoy a relaxed afternoon — snorkel the nearby Cistern Point, browse the Cooper Island Beach Club’s eco-boutique, and enjoy a locally brewed beer or handmade gelato as the sun sets over Salt Island.
A short hop brings you to Spanish Town, where you can pick up a mooring or dock for easy access ashore. Don’t miss a visit to the world-famous Baths National Park — explore the granite boulders, hidden pools, and sandy tunnels before enjoying a leisurely lunch at Top of the Baths. It’s a great day to stretch your legs on land and recharge for the next sail north.
Sail up the scenic coastline of Virgin Gorda into North Sound, one of the BVI’s most sheltered natural harbors. Leverick Bay offers excellent facilities, great protection from the easterlies, and easy access to shore. Spend the afternoon enjoying the swimming pool or beach bar, browse the shops, and don’t miss the Michael Beans Happy Arrr Show for a fun island evening of live music and laughter.
Enjoy a rewarding sail west across the Sir Francis Drake Channel to Cane Garden Bay, one of Tortola’s most scenic beaches. This stop is best in settled weather or light southerlies. Once moored, explore the beach bars and restaurants, sample local rum at the Callwood Distillery, or enjoy live music and dancing as you bar hop down the beach!
Sail west to Diamond Cay on Jost Van Dyke and head ashore to Foxy's Taboo, a lovely spot for lunch and a short walk to the famous Bubbly Pool — a natural seaside jacuzzi that comes alive when the surf rolls in. After exploring and enjoying the refreshing pools, make the short hop around to Great Harbour for the night. This well-protected anchorage is ideal in stronger winds and offers easy access ashore for dinner, drinks, and live music at Foxy’s Bar — the perfect way to toast your final evening on Jost.
Sail back across the channel to Little Harbour, Peter Island, a calm, sheltered cove ideal for your final night afloat. It’s a peaceful anchorage with excellent protection, perfect for swimming, paddleboarding, or simply relaxing on deck. Enjoy a quiet onboard dinner under the stars before returning to Nanny Cay the following morning — a serene end to your windy-weather sailing adventure.
Enjoy a relaxed final sail across the Sir Francis Drake Channel back to Nanny Cay Marina, home of Horizon Yacht Charters. Take your time departing Little Harbour, perhaps with a morning swim or breakfast on deck before raising the sails one last time. As you approach Tortola, you’ll pass the familiar landmarks of the Channel — a perfect moment to reflect on a week of great sailing, island adventures, and new skills gained. Once docked, refuel, refresh, and celebrate the end of your Caribbean sailing journey with a cold drink at Captain Mulligans, Omar's or Peg Legs Restaurant — just steps from the Horizon base.