The British Virgin Islands are the bareboat capital of the Caribbean — and for good reason. The Sir Francis Drake Channel between Tortola and the southern islands is one of the most beautiful stretches of water in the world, and the sailing is uncomplicated: consistent trade winds from the east, short passages between islands, sheltered anchorages, and a comprehensive system of mooring buoys that reduces the need to anchor in coral. This itinerary completes the classic BVI circuit in a week, suitable for skippers with coastal sailing experience and a valid sailing qualification. The BVI season runs November to April; hurricane season runs June to November.
Day 1: Tortola — Arrival
The main charter bases are in Road Town (the capital) and at Nanny Cay and Soper's Hole on the west end of Tortola. Collect the boat, complete the briefing, and spend the first afternoon provisioning. Road Town has a large supermarket; Soper's Hole has a small market and excellent rum shops. Clear customs and immigration if arriving from overseas — the BVI is a British Overseas Territory but requires a separate customs clearance from other Caribbean islands.
Day 2: Tortola to Virgin Gorda — The Baths
The Baths at the south end of Virgin Gorda are the BVI's most famous attraction — enormous granite boulders forming sea caves and grottoes at the water's edge. Pick up a mooring buoy off The Baths (anchoring is prohibited in the protected area) and take the dinghy ashore. Arrive before 0900 or after 1600 to avoid the day-tripper boats from Road Town. Swim through the grottoes — the light effect inside is genuinely spectacular.
Continue north to Spanish Town (Virgin Gorda's main settlement) for the night — the Yacht Harbour marina has good facilities and a waterfront restaurant strip.
Day 3: Virgin Gorda — Gorda Sound (North Sound)
Gorda Sound, enclosed by Virgin Gorda and the outer islands of Prickly Pear and Mosquito, is the finest anchorage in the BVI. The Bitter End Yacht Club (rebuilt after Hurricane Irma in 2017) dominates the north shore; Saba Rock is a tiny island in the middle of the sound with a good bar and restaurant. Pick up a mooring buoy or anchor in the sand. The kitesurfing conditions in Gorda Sound are exceptional.
Day 4: Anegada — The Outer Island
Anegada is the only coral island in the BVI — flat, ringed by reefs, and home to 200 people, a flock of flamingos, and the best lobster in the Caribbean. The passage from Gorda Sound requires careful navigation — the Anegada Reef extends several miles south and east of the island and has wrecked more than 300 ships. Follow the waypoints precisely and do not cut corners. Anchor off Pomato Point or take a mooring in Setting Point. The lobster at Dotsy's or the Anegada Beach Club — grilled whole, with rice and plantain — justifies the navigation anxiety.
Day 5: Anegada to Jost Van Dyke
The longest passage of the week — 25 miles from Setting Point west to Jost Van Dyke. The trade wind is behind you most of the way; in a 15-knot breeze the passage takes 4 hours on a broad reach. Great Harbour on Jost Van Dyke is home to Foxy's — the Caribbean's most famous beach bar, and the reason most BVI itineraries include Jost. White Bay, around the headland to the west, has the Soggy Dollar Bar (allegedly named for the wet currency of swimmers landing from boats at anchor).
Pick up a mooring buoy in Great Harbour or White Bay. White Bay mornings are quiet; the afternoons are not.
Day 6: Jost Van Dyke to Norman Island
Norman Island is the southernmost island in the BVI and the supposed inspiration for Treasure Island. The Bight — a wide, sheltered bay on the north coast — has over 100 mooring buoys and The William Thornton, a converted Baltic trading schooner that serves as a floating bar and restaurant. The caves at the south-west tip of the island are snorkellable from the dinghy — bring an underwater torch.
Day 7: Norman Island to Cooper Island and Return
Cooper Island Beach Club has a craft rum bar and a beachside restaurant that makes a fine final morning stop before returning to Tortola. The passage back to Road Town or Soper's Hole takes 2–3 hours. Hand the boat back clean and fuelled; the charter companies are efficient and the handover is typically quick.
Safety Notes
The BVI trade winds are reliable but the squalls that accompany them are not always predictable. A line of cumulus building to the east in the afternoon means a squall within the hour. Reef in time. The mooring buoy system in the BVI is well-maintained but individual buoys vary in condition — always inspect the pick-up line and through-hull fitting before attaching. Do not anchor in coral; the mooring buoys exist specifically to protect the reef.
Frequently Asked Questions
Q: Do I need a sailing qualification for bareboat charter in the BVI?
A: Yes. Most operators require an RYA Day Skipper (practical) or equivalent, plus a logbook showing recent sailing experience. Some operators run a checkout sail before release — be prepared for this.
Q: When is hurricane season in the BVI?
A: June to November. The BVI was severely affected by Hurricane Irma in September 2017; most infrastructure has been rebuilt, but check the current status of any marina or anchorage before booking. Peak charter season is December to April.