A winter cruise to the Caribbean islands, and how the season works

The Caribbean has a calendar that suits the British almost too well. Its official hurricane season runs from 1 June to 30 November, and the busiest stretch of it falls in late summer and autumn. Then, as the days shorten at home, the islands settle into their dry season: steady trade winds from the east, warm sea, blue skies broken by the odd short shower, and evenings that never quite cool. That is why the cruise season and the British winter coincide, and why so many voyages leave in December, January and February.

It is not a guarantee. A shower in the Windward Islands can last an afternoon, and the dry season is drier on some islands than others. But from about December to April the odds are on your side, and the sea is at its kindest.

Two ways to get there

The first decision is whether to fly or to sail.

A fly-cruise starts in the Caribbean itself. You fly out from Britain, join the ship in port, and spend the whole voyage among the islands: a fortnight can take in ten ports or so, with few days at sea. Barbados is the usual starting point for British travellers. Bridgetown has a deep-water port, the island has direct flights from the UK, and it lies at the eastern edge of the chain, so a ship leaving it can work its way through the Windward and Leeward Islands with the trade wind behind it.

The alternative is to sail all the way. A voyage from Southampton crosses the Atlantic in both directions, usually by way of the Canaries or Madeira, and so spends many days of a month-long cruise at sea. That is either the point of the holiday or a reason to fly, depending on how you feel about a sea day with a book. What it gives you, besides no flights, is the slow change of season: you leave England in the dark of December and wake one morning in the trade winds.

The season has its own shape, too. December brings the Christmas and New Year sailings, which are popular and worth booking early. January and February are the heart of the dry season, with settled weather and the coolest nights, which in the Caribbean means a light layer after dark rather than a coat. March and April are warm and often quieter, and on several islands the carnivals held before Lent fall in February or March. By May the season is fading, the air is growing heavier, and June, and the start of the hurricane season, is not far off.

The islands on the routes

The ports on these itineraries are a fair cross-section of the Caribbean. Castries in Saint Lucia sits below green volcanic hills. Kingstown, on Saint Vincent, is the gateway to the Grenadines, and Bequia the largest of its own Grenadines. St George's in Grenada is a horseshoe harbour of red roofs. Road Town in the British Virgin Islands, Philipsburg on the Dutch side of Sint Maarten, Basseterre in St Kitts and St John's in Antigua are the northern Leeward Islands, close together and quite different in history and character. And far to the south-west, off the coast of Venezuela, Aruba, Bonaire and Curaçao, the Dutch ABC islands, are drier, flatter and usually out of the hurricanes' way.

Voyages that go there

Ambassador Cruise Line's fourteen-night Caribbean Explorer - Tropical Isles flies from Heathrow and sails from Bridgetown in January. It calls at Kingstown, Castries, Oranjestad in Aruba, Willemstad in Curaçao, Kralendijk in Bonaire, Pointe-à-Pitre in Guadeloupe, St John's, Road Town and Philipsburg, so it reaches both ends of the chain.

A second fourteen-night Caribbean Explorer - Tropical Isles from Bridgetown, departing in February, takes a different line: Willemstad, Fort-de-France in Martinique, Pointe-à-Pitre, Basseterre, Philipsburg, St John's, Roseau in Dominica and Road Town.

For the long way round, Fred. Olsen's thirty-one-night Caribbean Christmas Island-Hopping leaves Southampton in December. Its ports are Santa Cruz de Tenerife, St John's, Philipsburg, Basseterre, Castries, Bequia, St George's, Bridgetown and Funchal on Madeira.

Which to choose comes down to time and temperament. Two weeks and two flights buys the most islands. A month at sea buys the journey, and a Christmas in the sun at the end of it.