The British Virgin Islands is the sailing capital of the Caribbean — the island group where the protected Sir Francis Drake Channel between Tortola and the outer islands has produced the most concentrated bareboat and crewed charter sailing circuit in the world. The Bitter End Yacht Club at North Sound, the Soggy Dollar Bar at White Bay on Jost Van Dyke (the beach bar most associated with the Painkiller cocktail and the BVI sailing life), and the luxury villa and resort culture of Virgin Gorda combine to produce a wardrobe context that is simultaneously more nautical and more relaxed than most Caribbean destinations.

For the BVI sailing circuit. The charter yacht between the islands — natural swim shorts and a white PP linen shirt for the boat deck; leather deck shoes. The anchorages: the Bight at Norman Island, the Caves, the Dog Islands. Natural swim shorts for the snorkelling stops; the PP linen shirt back on for the boat.

For the Bitter End Yacht Club and the North Sound. The sailing hub of the BVI — the marina, the moorings, the water activities of North Sound. The most actively nautical and most relaxed social context in the BVI. White PP linen over natural swim shorts throughout.

For Virgin Gorda. The Baths — the extraordinary boulder-strewn beach at the southern tip. Natural swim shorts and a white PP linen shirt for the approach; the same combination for the beach. The Rosewood Little Dix Bay for the luxury resort context of Virgin Gorda — white PP linen for the beach, navy for the resort evening.

For the Jost Van Dyke. The island beach bar culture — the most relaxed and most social context in the BVI. White PP linen over natural swim shorts, leather sandals.

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