British Virgin Islands

The British Virgin Islands are the most-chartered cruising ground in the Caribbean, and one of the most-chartered anywhere in the world. The chain is around sixty islands and rocks scattered between the eastern end of Puerto Rico and Anegada, of which only sixteen are inhabited. The islands have been British since 1672, and they sit close enough together that a charter mostly sails by sight: the next island is rarely more than an hour away, which is what makes the BVI the easiest first crewed charter most clients ever take.

Norman Island, at the western end of the chain, is one of several islands claimed as the inspiration for Robert Louis Stevenson's Treasure Island, and the connection isn't entirely fanciful: in 1750, a mutinied Spanish galleon called Nuestra Señora de Guadalupe really did bury its silver there, and locals from Tortola really did dig some of it up. The Bight, the natural harbour at Norman Island, is still one of the best first-night anchorages in the Caribbean. From there, most charters work east along the chain, taking in The Baths on Virgin Gorda, where massive granite boulders form sea-pools you swim through, and Anegada at the top, the only coral atoll in the chain and the source of what charter regulars argue is the best lobster in the Caribbean.

The trade winds blow steady from the east through the dry season, which runs December to April, and they are the reason most charters here run a counterclockwise loop with the wind on the beam most days. Most BVI charters pick up in Tortola at one of the marinas around Road Town or West End. A week is the standard charter; the BVI is small enough to do it well in that time, and big enough to make you want a second one.