Caribbean

The Caribbean is shorthand for at least four different yacht charter regions, each with its own rhythm. The British Virgin Islands are the close-knit chain of around sixty islands where line-of-sight sailing was made famous, and which still anchor the largest charter fleet in the region. The Bahamas, technically Atlantic rather than Caribbean, run from Bimini to Inagua across 800 kilometres of clear bank water, with the Exumas in the middle as the headline. The US Virgin Islands offer Trunk Bay on St John, one of the best-rated beaches anywhere, and the easiest first port if you're flying in from the United States. South of those, the Windward and Leeward chain runs from Anguilla and Sint Maarten down to Grenada, with Antigua, St Barths, St Lucia, Dominica and the Grenadines as the main charter stops along the way.

Each chain has its own character. St Barths is the celebrity-and-yacht-show one, busy through the winter event weeks. Antigua is the racing capital, with Antigua Sailing Week and the Caribbean 600 drawing fleets every spring. Dominica is the wild one, with mountains rising to 1,400 metres straight out of the sea and whale-watching off the west coast year-round. The Grenadines (Mustique, Bequia, the Tobago Cays) run for about 60 nautical miles between St Vincent and Grenada, and they offer some of the best small-island anchorages in the eastern Caribbean.

The high season for all of it is December to April, when the trade winds blow steady from the east and the rain backs off. Most charters pick up in St Maarten, Antigua, St Lucia or Grenada depending on the route. A week works for any one chain; two weeks lets you string two together, with a positioning passage or a flight in the middle.