The Leewards are the heart of Caribbean charter — St. Barths at New Year, Antigua’s sailing heritage and harbours, and short hops between islands in steady trade winds. The winter season delivers some of the finest sailing anywhere, with glamour and seclusion within the same week.
The marquee anchorages and harbours of Leeward Islands. Select a point on the map to read about it.
The most glamorous island in the Caribbean, peaking around New Year when Gustavia’s harbour fills with the world’s finest yachts.
365 beaches and deep sailing heritage — English Harbour and Nelson’s Dockyard are the historic heart of Caribbean yachting.
Low, quiet and ringed with dazzling beaches — a serene, exclusive contrast to St. Barths just across the channel.
A dual-nation island and practical hub, with excellent provisioning, lively harbours and a great anchorage at Marigot.
The difference between a good charter and an unforgettable one is knowing where to be, and when — the anchorages worth the detour, the timing that avoids the crowds, the table worth booking ahead. Tell us your dates and we’ll send a sample itinerary built around them.
The yachts that sail these waters are among the finest afloat — and the best weeks are taken early. Tell us your dates and we’ll match you with crewed yachts available for Leeward Islands, and send a considered selection.
Enquire about chartering Leeward Islands