Foxy Callwood opened his first bar at Jost Van Dyke in the 1960s when the only way to arrive was by sailing vessel, and the island has maintained that affinity with sail ever since. A classic yacht anchored in Great Harbour draws admiring glances from the beach and is treated with genuine interest by the community: locals can usually name the yard, the designer and the approximate year of build by the shape of the bow and the cut of the rig.
The classic charter fleet in the BVI numbers around eight vessels across any given season, including gaff-rigged ketches, traditionally planked sloops and a small number of performance racing yachts built in the 1980s and 1990s that have aged into classics in their own right. Jost Van Dyke suits all of them: the passages are protected, the anchorages are predictable, and the trade wind delivers a proper sailing experience without the demands of open-ocean passage-making.
Weekly rates for classic charter yachts in the BVI range from 50,000 to 120,000 euros, depending on length, specification and crew quality. The advance provisioning allowance of around 30 percent covers provisioning, marina fees and fuel for engine passages. The classic charter season in the BVI peaks between January and April, when the northeast trades blow at their most consistent and the sea state in Drake Channel is manageable for any classic vessel.
From Great Harbour the classic yacht circuit visits Sandy Cay and Green Cay on the eastern tip of Jost Van Dyke before pressing south toward Norman Island’s Caves, a beam reach in 18 knots that suits any well-found ketch. The return passage north, beating into the trades past Peter Island and across to Jost Van Dyke, is the kind of windward work that reminds crews why these boats were designed the way they were.
