Top 10: Caribbean holidays with culture
2. Charlestown, Nevis
Nevis has one of the most charming capitals in the Caribbean. Unspoilt by development, Charlestown still has attractive Georgian buildings and a sociable, village-like atmosphere. Park at the northern end near the Alexander Hamilton Museum then make a clockwise loop walking down Main Street and back along the seafront. On the way you can buy fruit at the market and follow signs leading to historic sights such as the Methodist Church, built by freed slaves in 1844, and the somewhat forlorn Jewish Cemetery. The Four Seasons hotel is just up the coast from Charlestown (01 869 469 1111; fourseasons.com/nevis; from £237 room only). Nigel Tisdall
Charlestown, Nevis (Fotolia/AP)
3. Bermuda
Bermuda might share the same latitude as South Carolina, but it has a Caribbean soul. The climate is sub-tropical, 60 per cent of islanders are of West Indian heritage, and there are good beaches and rum. It is also Britain’s oldest and most prosperous overseas territory with a rich maritime history – the 1814 Royal Naval Dockyard houses absorbing museums. In the capital, Hamilton, the 44-room Rosedon Hotel (rosedon.com) is set in a stylish 1906 mansion with gardens and a pool. Booked through Prestige Holidays (01425 480400; prestigeholidays.co.uk/bermuda): from £1,857 with breakfast. Nigel Tisdall
4. Island tour, Cuba
Travel the Unknown (020 7183 6371; traveltheunknown.com) knows Cuba very well. Its 13-day escorted Eastern Cuba Explorer tour takes in the island’s well-trodden highlights such as Havana, Trinidad and Santa Clara, but also goes off the beaten track for Matanzas, rich in musical and cultural history, and Guantánamo. The final stop is beautiful Baracoa, my favourite place in Cuba after Havana. All nights are in casas particulares (private BBs) – staying with locals is one of the best ways to understand this complex island nation. Arranged as a private tour for two, from £2,295 per person, including breakfasts. Claire Boobbyer
Wall art in Matanzas, Cuba (Fotolia/AP)
5. Ponce, Puerto Rico
Puerto Rico is an engaging Caribbean-US fusion, where salsa, rum and tropical beaches are married with baseball, malls and multi-lane expressways. The island is best explored on a self-drive holiday. Follow the Ruta Panorámica through the interior and relax on the west-coast surfer beaches. Don’t miss Ponce, with its ornate buildings and the Museo de Arte de Ponce, which has one of the finest art collections in the Caribbean. Stay at the Ponce Plaza Hotel Casino (001 787 813 5050; ponceplazahotelandcasino.com): from £112 room only. Nigel Tisdall
6. Jamaica
There’s something effortlessly cool about the bushbar at Geejam (geejamhotel.com) in Port Antonio. Part hotel, part recording studio, Geejam is set among vast trees slung with rampant greenery, with scarlet drapes and cushions inside and the turquoise sea below – plus the ever-present, laid-back vibe of culture reggae. On Saturday nights, the Jolly Boys (mostly in their seventies) sing mento, an earlier Jamaican rhythm. Booked with Black Tomato (0207 426 9888; blacktomato.com): from £1,982. James HeTop 10: Caribbean heritage holidaysnderson
The Castillo Serrallés museum mansion in Ponce, Puerto Rico (Fotolia/AP)
7. Trinidad Carnival
People leave their jobs to get back for Carnival in Trinidad (February 8-9 in 2016). You can dance for days – at the pre-Lenten weekend of calypso singing and steel band competitions, at J’ouvert on the Monday before dawn, and the street parade on Lundi and Mardi Gras. Unlike Rio and New Orleans, you can join the street parade: contact a band (carnivalinfo.com), reserve a costume, turn up and dance. Stay in uptown Port of Spain at the cool Coblentz Inn (00 1 868 621 0541, coblentzinn.com): from £75 low season. James Henderson
• Trinidad and Tobago travel guide
8. Havana, Cuba
Hedonistic Havana is so much more than cigars, cocktails, classic cars and crumbling architectural grandeur. Delve deeper on a tailor-made city break organised by Audley Travel (01993 838 685; audleytravel.com), with salsa classes, a photography tour and a horticultural tour of one of Havana’s organic gardens. Your base is the Iberostar Parque Central, between the Old City and the fascinating streets of residential Centro with a rooftop pool. From £2,090, including breakfast. Claire Boobbyer
9. Guadeloupe/Martinique
The French Caribbean islands of Martinique and Guadeloupe have long been competitors, with Guadeloupe recently hitting our TV screens as the fictional Saint-Marie, location for Death in Paradise. You can stay close to the police station, at the Habitation Grande Anse (hotelhga.com) in Deshaies, a cool spot nestled in greenery. Onyx Travel (0118 947 2830; onyxtravel.co.uk) offers a week there in a studio, room only, from £780, flights via Paris, includes car hire. James Henderson
Nelson’s Dockyard, Antigua (Fotolia/AP)
10. Nelson’s Dockyard, Antigua
Atmospheric Nelson’s Dockyard – a national park in Antigua’s English Harbour – is the world’s only continuously working Georgian dockyard. It includes a museum, marina, shops and hotels – The Admiral’s Inn (admiralsantigua.com; £160 room only) has attractive, quirky rooms (best are the Gunpowder Suites). Fred Mawer
Tell us about your favourite Caribbean family holiday destination at telegraph.co.uk/caribbeanawards
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