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They say there’s an island for everyone in the Caribbean. Here, the empty white sands of the Turks and Caicos are juxtaposed with the all-inclusive party palaces of the Dominican Republic, while St Lucia’s Creole culture feels a million miles from the yachtie scene of the British Virgin Islands. However, while every island offers something different, they all have landscapes and climates that would fit most people’s definitions of paradise.

Dominating your world view is the Caribbean Sea itself — restless along east coasts, limpid in the west, yet always mesmerising, whether you’re sailing on it, swimming in it or simply staring at it. There’s the exuberance of nature: a grove of wild ginger lilies growing in an orchid-garlanded rainforest; a hawksbill turtle on a moonlit beach; and kaleidoscopic reef life only a few metres away from the shore. Colour is everywhere, and it is reflected in the cultures of people who can be at once devout yet joyful, studious but rhythmic, and rarely less than charming. History is tangible here, from the pirate lookouts of Shirley Heights, high above Antigua’s English Harbour, to the black-rock sugar mills of St Kitts and Nevis.

Apart from lying on white-sand beaches, drinking from a freshly harvested coconut and coping with the dilemma of whether to have grilled snapper or crab cakes for lunch? The Caribbean is an aquatic playground, and while motorised watersports are falling out of fashion in the increasingly climate-conscious islands, greener pursuits such as sailing, stand-up paddleboarding and kayaking have benefited from a massive rise in popularity.

The green theme extends inland, from gentle walks around the botanical gardens of Barbados to the exhilarating ascent of St Lucia’s magnificent Gros Piton and hikes across Dominica’s Morne Trois Pitons National Park*.

Dive sites in the Cayman Islands, Jamaica and Tobago should be on your list if you’re an experienced diver, but if you simply want to get Padi-qualified, you’ll find schools and fabulous places to learn on almost every island.

 Take on the exhilarating ascent of St Lucia’s magnificent Gros Piton

Above all, make time for the people; they’re the route to the true heart of the Caribbean. Seek experiences such as a game of dominoes in a Jamaican rum shop (you’ll lose); a Friday-night barbecue on Anguilla (you’ll dance); a Sunday church service in Bridgetown, Barbados (you’ll cry) — and, if you’re really lucky, an invitation to somebody’s house for dinner (take a cake).

Most holidaymakers plump for a hotel, and there are properties to suit all tastes. For all-inclusive family resort hotels the Dominican Republic and Jamaica are the top choices, while Antigua and Barbados’s Platinum Coast specialise in white-gloved five-star hospitality. St Lucia’s southwestern coast is home to a number of honeymoon favourites — especially anywhere with a view of the Pitons — as is Anguilla’s West End. For the castaway experience, albeit in comfort, try the North and Middle Caicos or St Vincent, and if you seek a beach with French chic, choose Saint Barthélemy (usually shortened to St Barths) or Guadeloupe. Tobago and Dominica are good for eco-lodges, Nevis is the best at antique-filled plantation houses, and Cuba’s casas particulares offer guests utterly unique homestay experiences. The alternative is a villa, with or without a butler, driver and private chef. St Barths leads the region in choice, Jamaica’s Ocho Rios is top for luxury, and Barbados has a villa or a house for every budget.

Wherever you choose, remember that the Atlantic-facing eastern shores of the Lesser Antilles — that’s the arc of islands from the British Virgin Islands in the north to Trinidad and Tobago in the south — have significantly rougher seas than their sunset sides.

Given lots of time and money you could go island-hopping in the Caribbean from one party to the next, with the Trinidad and Tobago Carnival the first big event of the year. Held in the week of Mardi Gras, the party was taken from the gentry by the people after the 1833 Emancipation Act and is now considered the root of calypso.

In April, English Harbour hosts Antigua Sailing Week, the Caribbean’s biggest regatta. May brings the beginning of St Lucia’s summer celebrations, starting with the Roots and Soul Festival, continuing with Carnival in July and ending with the internationally famous Jazz Festival.

You could go island-hopping in the Caribbean from one party to the next

In Barbados, Crop Over is a party that originated in the celebration of the completion of the cane harvest. It’s since become a five-week festival of music, culture, food and drink, taking place over July and August, and would be the most important event in the Caribbean were it not for cricket.

Peak season across the Caribbean runs from December to the end of April. Prices are at their highest, humidity and rainfall are at their lowest and average temperatures bask in the late 20Cs. By June that average is in the early 30Cs and the air is getting wetter, and come August you can expect rain most days. That said, the showers, which can be spectacularly heavy, tend to coincide with afternoon nap time and leave spectacular sunsets in their wake. The Atlantic hurricane season runs from June to November, with frequency and intensity peaking in September and October, and many hotels and tourism businesses close for the period. That leaves the shoulder months of May and November — known in the trade as secret season — when prices are low and weather, but for the odd shower, is lovely.

Which Caribbean island has the best beaches?
It’s a matter of considerable debate, but, having visited 33 of the islands, I would pick the Middle Caicos for wildness, Antigua for choice (it has 365 beaches, as you’ll certainly be reminded), and Anguilla for beauty.

Which is considered the most beautiful Caribbean island?
Beauty is in the eye of the beholder, but it’s hard to think of any part of the Caribbean more picturesque than southwestern St Lucia, where lush, jungle-covered slopes plunge from the flanks of the smoking Qualibou volcano into a turquoise bay and the Pitons jut from the sea like green dragon’s teeth.

Currency
Anguilla, Antigua, Dominica, Grenada, Montserrat, St Kitts and Nevis, St Vincent and the Grenadines: East Caribbean Dollar
Guadeloupe, Martinique, St Barths, St Martin: Euro
Bonaire, BVI, Puerto Rico, Turks and Caicos, USVI: US Dollar
Bahamas: Bahamian Dollar
Barbados: Barbadian Dollar
Cuba: Cuban Peso
Dominican Republic: Dominican Peso
Jamaica: Jamaican Dollar
Trinidad and Tobago: Trinidad and Tobago Dollar

Details

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