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
Famous for the mysteries of the Bermuda Triangle, Bermuda is a British Overseas Territory in the Atlantic Ocean. Although referred to in the singular, there are actually 181 islands making up the country; the largest of which is known as Main Island. Travellers flock to sit on the famous beaches of pink sand with vibrant blue water, or to try their hand at scuba diving to explore the coral reefs and shipwrecks that are littered on the seabed. Attractions for visitors include the Crystal Caves complete with stalactites and underground saltwater pools, the Botanical Gardens and glass bottomed boat tours. Those who like to try something a little bit different will be pleased to find that they can try ‘helmet diving’; walking along the seafloor with a weighted glass helmet through which to view the brightly coloured ocean life. Bermuda is an easy country to visit with children; there are plenty of kids’ playgrounds around Main Island as well as family focused resorts. From London, flights to Bermuda take seven and a half hours.Take me to Bermuda
Like the Cayman Islands, the British Virgin Islands (‘BVIs’) are a British Overseas Territory in the Caribbean Sea and consist of over 50 regions; four main islands with over 50 smaller ones. Only around 15 of these are inhabited and the largest of the islands is just 20 km long. Number one on the list of Tripadvisor’s recommended attractions is visiting The Baths in Devil’s Bay National Park on Virgin Gorda island; these are incredible rock formations (created by volcanic eruptions) that allow sunlight to beam in, creating beautiful patterns in the cave-like spaces underneath. Other family friendly days out include visiting flamingos flocking at the salt ponds on Anegada; chartering a boat to see the islands from the water; and taking a hike around Biras Creek Trail to spot colourful birds and bright green iguanas. Accommodation on the British Virgin Islands is good, with plenty of family resorts along with a few smaller hotels. Flights from London to the British Virgin islands takes around 14 hours.
A British Overseas Territory nestled in the warm waters of the Caribbean Sea, the three Cayman Islands are where many people visualise when they think of paradise. This trio is perfect for a multi-island holiday, as each has its own unique vibe and activities. The smallest island is a haven for many kinds of wildlife, from the comically named red-footed Boobie birds to endangered species of lizard. Little Cayman has a tiny population of just 170 people, giving it an almost deserted island feel; that is until Mardi Gras or Pirates Week celebrations kick off! Cayman Brac has a dramatic landscape of rugged rock-face and wild flora and fauna as well as limestone caves and sinkholes to explore. If you’re looking for more of a traditional family holiday, Grand Cayman is the largest of the three and offers attractions such as swimming with stingrays, visiting a plantation home from the 1700s and snorkelling in crystal clear waters. Flights from the UK take around a day with one or two stops.Take me to Cayman Islands
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
This Caribbean nation shares the island of Hispaniola with Haiti and is set just west of Puerto Rico. Well-known to golf enthusiasts, there are several five-star courses for those looking for a relaxing day without the kids. There are seven international airports that make hopping across the pond a breeze, and the warmth and friendliness of the locals towards tourists is well known. Dominican beaches are stereotypically Caribbean, with white sand and vivid blue water. There are hotels for every budget, from all-inclusive family resorts to hostels and homestays for those happy with more basic accommodation. The Dominican Republic is home to some unique wildlife, notably the smallest gecko in the world and the rhinoceros iguana. Check out the old town of Santo Domingo for picturesque architecture and an insight into the country’s history and traditional Hispanic culture. Flights from the UK take around 12 hours.Take me to Dominican Republic
A postcard-worthy tropical paradise, St Lucia is a sovereign island nation nestled like an emerald in the Caribbean Sea. Historically rich in sugar plantations, nowadays the island has turned to tourism for one of its main sources of income. Visitors can still stay among 250 year old working sugar plantations and get a feel of old-world island life, or cosy up in one of the luxury all-inclusive resorts. Nature is the main attraction here, with stunning national parks, waterfalls and botanical gardens to hike through. The usual scuba diving and snorkelling is on offer, as well as more relaxing ways to see the island such as Segways or private coach tours. Water parks and horse riding are popular family friendly activities and the locals welcome children with warm smiles and an easygoing nature. Kids will jump at the chance to explore the chocolate making process from one of St Lucia’s cocoa estates; Hotel Chocolat has a hotel on the island and runs courses teaching chocolate-lovers all about the process of making the sweet treat from bean to bar. Flights from London to St Lucia take around 12 hours.Take me to St Lucia
Voted home to the ‘best island in the world’ as well as the ‘best beach in the world’, the Turks and Caicos archipelago takes breathtaking beauty to another level. Despite these high accolades, the islands are still relatively uncrowded and provide enough space for travellers to visit without it impacting on the laidback vibe. Enjoying a multi-centre holiday by hopping around the 40 islands, only eight of which are inhabited, is a great option for people who like variety and want to see a lot in a short space of time. The tourist centre of Providenciales is busier than some of the other islands and this is where you’ll find the acclaimed Grace Bay as well as plenty of family resorts and hotels. Grand Turk is the cultural and historic capital, where visitors can see Bermudian architecture and enter the National Museum to find out about the history of the islands and their inhabitants. Middle and North Caicos are home to lush woodlands, caves and ponds; perfect for families who want more of an unplugged break among beautiful nature. Flights from London take around 12 hours.Take me to Turks and Caicos
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.
South of the British Virgin Islands lay the US counterparts; the United States Virgin Islands. Previously central to the slave trade, now the islands have a thriving tourist trade with visitors learning all about the history and cultural roots of the inhabitants through local tours. Artisans and crafters sell beautifully decorated homeware and mahogany pieces, and daily cultural demonstrations include how to cook on a coal pot over an open flame. Music lovers will enjoy the sound of ‘scratch’ bands, a traditional sound created when the ban on drums and dancing was imposed by strict Dutch laws. African twists have been put on European dances such as the jig and the quadrille, with the dancers wearing madras costumes and hand made head ties. Animal lovers will enjoy taking a bird watching tour, spotting dolphins and whales off-shore and hiking the plentiful trails in the national park. During your stay be sure to try the local cuisine, with delicacies such as pumpkin fritters and potato stuffing making regular appearances in eateries around the isles. Flights from London take around 15 hours.