Easy Island Living: The British Virgin Islands
Short Sails, Legendary Anchorages and the Laid-Back Spirit of Caribbean Island Life
Introduction
Your journey begins at the quietly elegant Nanny Cay Resort & Marina on Tortola, a calm palm-lined harbour set within a relaxed boutique hotel complex. For a gentler start or a slower finish, you can extend your holiday with a stay at Nanny Cay beside your embarkation point.
From here, you sail towards Virgin Gorda’s sheltered bays, the soft sands of Anegada and the sunlit anchorages of Jost Van Dyke—Caribbean sailing at its most relaxed, luminous and effortlessly elegant.
British Virgin Islands Sailing Itinerary
Total distance 78 nautical miles · average 2–3 hours sailing daily
Day 1 - Tortola
Embark in Tortola, the BVI’s largest island and sailing hub. Explore Road Town’s colourful streets, shop for island crafts, or relax with a rum punch by the marina. Tortola’s lively spirit is the perfect introduction before casting off into the surrounding isles.
Day 2 - Spanish Town (Virgin Gorda)
Sail to Spanish Town on Virgin Gorda, gateway to the island’s famous Baths. Wander among giant granite boulders, hidden pools, and sandy passages. In town, enjoy a relaxed evening with local dining and harbourfront charm.
Day 3 - Virgin Gorda (North Sound)
Continue exploring Virgin Gorda with a visit to the sheltered North Sound. Anchor in idyllic bays such as Leverick or Bitter End, where calm waters and luxury resorts meet beach bars and island hospitality. Snorkelling and watersports abound in this famous sailing haven.
Day 4 - Anegada
Anegada is unlike the other BVIs — a flat coral island surrounded by reefs and white-sand beaches. Explore by scooter or jeep, spot flamingos in salt ponds, and feast on freshly caught lobster grilled on the beach at sunset.
Day 5 - Jost Van Dyke
Known for its barefoot beach bars, Jost Van Dyke is the BVI’s party isle. Anchor in White Bay, home of the famous Soggy Dollar Bar, or explore Great Harbour’s laid-back vibe. It’s the perfect mix of fun, relaxation, and Caribbean rhythm.
Day 6 - Norman Island
Believed to have inspired Robert Louis Stevenson’s *Treasure Island*, Norman Island is rich with legends and hidden caves. Snorkel at The Indians, swim through sea caves, and dine aboard a floating bar — a true sailor’s playground with a dash of adventure.
Day 7 - Tortola (Return)
Return to Tortola for a final evening ashore. Wander the lively streets of Road Town, shop for souvenirs, or toast your voyage with a rum cocktail overlooking the marina — a fitting finale to a week of Caribbean island-hopping.
Optional Onshore Experiences
Enhance your voyage with hand-picked experiences ashore, blending the region’s rich culture with its celebrated cuisine.
Cultural Moments
The Baths, Virgin Gorda: Wander through giant granite boulders, sandy tunnels, and hidden pools in one of the Caribbean’s most iconic natural sites.
Anegada Wildlife: Spot flamingos and explore salt ponds on the BVI’s only coral island, where reefs and white sands create a unique landscape.
Road Town, Tortola: Visit historic sites and colourful streets in the BVI’s capital, blending island heritage with vibrant markets and marina life.
Cuisine Journeys
Anegada Lobster: Feast on freshly caught lobster grilled on the beach, paired with sunsets over turquoise seas.
Soggy Dollar Bar: Sip rum cocktails in Jost Van Dyke’s legendary barefoot beach bar, the birthplace of the Painkiller.
Norman Island Dining: Dine aboard a floating bar after snorkelling sea caves and reefs, a perfect mix of flavour and adventure.
View the Elysian Experience
Sail & Stay – Extend Your BVI Escape
Make your holiday 10–14 days by adding a stay at the relaxed, palm-fringed Nanny Cay Resort, set within the calm marina where your yacht awaits.
Begin with a soft arrival—a gentle way to settle into Caribbean warmth before you set sail. Or choose a slow departure, unwinding for a few extra nights after your week exploring the BVI’s quiet bays and luminous turquoise waters.
A Sail & Stay extension offers the perfect blend of boutique comfort and relaxed indulgence, completing your journey with ease, elegance and the soft, sunlit charm of the British Virgin Islands.
Continue Your Journey
Explore the yachts selected for this itinerary, or view the sailing route in more detail.
