From the coast of Florida almost all the way to Venezuela, the Caribbean lies like a narrow chain between North and South America.
The region’s always lured adventurous travellers: often flying the Jolly Roger or planting a flag of nation – some islands are still US, UK, French or Dutch territory. Happily, buccaneering and colonising are mostly consigned to history now, but the remarkable weather, beaches and way of life that appealed centuries ago is just as irresistible today as ever.
There are bits of the Caribbean best left to weekending Manhattanites, trust-fund college students and cruise ships. But that still leaves dozens of islands where kids are the most welcome guests of all and family holidays don’t come much better.
Temperatures seldom drop below 20˚C on Antigua & Barbuda and, in summer, high-30s are not unusual. But the trade winds which first attracted Admiral Lord Nelson to this gorgeous little island in 1784, make for delightful days on the beach and marvellous sailing most of the year. Another former colony with direct flights from the UK, this is the perfect choice for a relaxed, family resort holiday.Take me to Antigua & Barbuda
Less than an hour’s flight from Miami, the Bahamas’ cluster of 700 islands is a weekend break from the city, first port of call for almost every luxury cruise and has family holidays down to a fine art. This is historic pirate territory and they say Atlantis lies beneath the clear blue waters – give it five minutes and that doesn’t seem entirely implausible. Nassau & Paradise Island, Grand Bahama and the Abacos are great for kids with outstanding resorts and endless activity, but not at the expense of traditional Caribbean character or thrilling history. And you can island hop as part of the experience in the Bahamas, so choosing a lively base doesn’t deprive you of gentler, quieter escapes from time to time.Take me to Bahamas
A former British colony, Barbados has direct flights from London all year round. English is spoken everywhere here and it’s one of the least expensive islands for accommodation, activities and eating out. But Barbados is still beautifully Caribbean from flawless beaches and sunshine to amazing history, Creole customs and the gentle, lilting accent, which makes even your mother tongue sound exotic.Take me to Barbados
Cuba is the Caribbean’s biggest island by far, but tourism here is still relatively new. So it’s not the place for big brand attractions and that’s part of the charm. Atmospheric and lovely World Heritage Havana is a grand, colonial city. People really do drive around in 1950s American classics, music plays all the time and entertaining kids endlessly is a matter of civic pride. On the acres of beaches you can have traditional seaside fun packed with water sports, snorkelling, diving and sailing or you can just laze around and take it easy on island time. Touring the smaller cities, dipping into the unspoiled countryside and exploring Cuba’s long and intriguing history makes unforgettable holiday memories for older kids. And most of the country’s accommodation is still state-managed, so whether you want the family-run friendliness of a Casa Particulares or the Cuban version of a luxury resort, staying here is very good value compared to elsewhere in the Caribbean.Take me to Cuba
Spice is part and parcel of the Caribbean, but only Grenada is known as Spice Island. Even the air in the delightful capital, St. George’s, is laced with rich, delicious scents and a history of trade, daring and riches lost and won, infiltrates ever corner of this one-time British colony. For exploring rainforests, a warm and local character and wonderful food, Grenada is perfect. It has some of the region’s most beautiful beaches too and kids love the sea-faring tales, living heritage adventures and astonishing range of outdoor activities on land and underwater.
Jamaica practically invented the concept of the all-inclusive resort holiday and Montego Bay alone has several of the world’s most impressive hotels. But it’s also one of the most popular islands for families and an excellent choice for self-catering villas and holiday apartments. Naturally, the birthplace of several Olympians isn’t short on outdoor fun and an accessible jungle landscape makes everything from rafting and wild swimming to hiking in the mountains a possibility, even for younger kids. Kingston is one of a kind; a brilliant, boisterous city laced through with easy going island spirit that’s a part of everything from museums and galleries to music and plates piled high with amazing Caribbean food – hot sauce comes on the side, so you can ease children gently into the legendary spiciness. And, even if you do nothing but lie on the sand and paddle when it gets too hot, Jamaica is blissful.
St. Kitts is small enough to tour in a day, if you can resist stopping off at the beautiful beaches or avoid the intriguing history. This was one of the first Caribbean islands to be recorded – Columbus set his sights on it in the late 15th century. It has a long pirate legacy and fantastic hill forts to prove it. Young kids love the relaxed, barefoot atmosphere. And the accommodation here covers everything from boutique guesthouses to 5-star, family-friendly resorts.
You can have one without the other, but the most southerly of the Caribbean islands are almost always linked in the imagination. In reality, they’re vastly different but share a warm friendliness and the type of spectacular weather you’d expect off the coast of South America. Trinidad is bright and modern in parts with a spirited outdoor life, lively beaches and, of course, a Mardi Gras Carnival rivalled only by Rio’s. Tobago does carnival season in September, wins awards for eco-tourism and holidays with much the same passion as its bigger neighbour, just a little less noise. If you had to choose? Trinidad is wildly good fun for older kids and teenagers and has plenty of sand and sea for younger children. And Tobago is the island less hurried and well loved by young explorers, mini-marine biologists and wildlife enthusiasts – but the beaches are just as good and there’s plenty of life, it’s a just a lot more low key and local.