Sailing yacht charter in Anguilla puts one of the Caribbean most consistent trade winds to work across a setting of extraordinary beaches and clear reef-lined waters. The island sits at the northern end of the Leeward chain, where steady 15 to 20 knot easterly trades give sailing yachts a reliable passage throughout the winter season. The Anguilla Channel between the island and St Maarten can build a steep chop in the afternoons, but morning departures give sailing yachts a clean approach to the island from almost any direction.
The sailing fleet available for charter around Anguilla counts approximately 19 yachts, spanning modern performance cruisers, classical ketch-rigged vessels and a handful of sailing catamarans suited to families and larger groups. Sailing yachts of 15 to 25 metres offer the greatest agility in Anguilla shallower anchorages, particularly around the cays to the west, while larger yachts are better suited to the deeper water off Road Bay and Meads Bay. All carry the water sports packages expected in the Caribbean.
Weekly charter rates for sailing yachts around Anguilla begin at approximately 50,000 euros for a 15-metre crewed vessel and reach around 250,000 euros for the largest sailing superyachts. The advance provisioning allowance, covering fuel, food, berthing and drinks, adds approximately 30 percent to the weekly fee.
Sailing itineraries from Anguilla traditionally include a passage north toward the Dog Island anchorage, a lazy reach down to Little Bay past the dramatic southwest cliffs, and a day-sail across to St Barths on a broad reach.
