Most holidays to the Caribbean begin with a juicy question: which island should we go for? It’s a delicious debate best done with a tot of rum in hand and a map showing the 29 options, and the good news is they all have their charms. These start with guaranteed warmth, bountiful sunshine, scenic splendour and charismatic people. Then comes the dream beaches, upbeat music, spiced-up cuisine, exuberant carnivals and a rich and diverse history reflected in 21 World Heritage Sites.

It was with these delights in mind, and the fact that this popular getaway is heading into its first full winter season for two years without Covid protocols, that Telegraph Travel crunched the data to identify the greatest Caribbean island of all.

Donning our best straw hats and floral shirts, we’ve compared the contenders across 24 criteria from bird species and golf courses to the cost of living and threat from hurricanes (see ‘Our methodology’, below). 

In the end, just a handful of points separated our top ten islands and the winner was a worthy one – it is one of the most distinctive and engaging destinations in not just this balmy region, but the world.

“The chance to snorkel and dive at over 70 sites is a chief lure.”

Forty miles north of Venezuela, this beach-dotted Dutch island is the perfect all-rounder and clocked up good scores for its plentiful five-star resorts, having little rain and being outside the hurricane belt. The colourfully-painted World Heritage-listed capital, Willemstad, offers a wealth of historic buildings in the Pietermaai neighbourhood while a steady stream of visiting cruise ships means the shopping is above average – health and beauty products using island-grown aloe vera are a top buy.

The chance to snorkel and dive from the shore at over 70 sites is a chief lure while Christoffel National Park has hikes and self-drive routes centred on the 1,239ft Christoffel Mountain, the island’s highest point. Curaçao is best reached via Amsterdam, with the journey taking around 12 hours. Accommodation options include the 351-room Sandals Royal Curaçao resort, opened in June, and the family-friendly Papagayo Beach Resort at Jan Thiel Beach with self-catering bungalows.

Sandals Resorts (0800 597 0002; sandals.co.uk) offers seven nights at Sandals Royal Curaçao from £2,810 all-inclusive per person, including KLM flights from London Heathrow via Amsterdam departing on December 7 with transfers.

“The island is blissfully free of brash resorts and mega-cruise ships.”

Two thirds of mountainous Dominica is rainforest, so it makes sense that it tops the ‘tree cover’ category. Rising up between the French territories of Guadeloupe and Martinique, the island is blissfully free of brash resorts and giant cruise ships, and suits active travellers who like to hike, dive and birdwatch. Thrills include the strenuous ascent to Boiling Lake, where the water steams like a witches’ cauldron due to volcanic activity, and snorkelling at Champagne Reef, where the sea is enlivened with bubbles for the same reason.

The hillside Jungle Bay resort, near Soufriere, makes it easy to explore with its ‘adventure wellness’ package that includes daily yoga and a 30-minute spa treatment plus activities such as hikes, kayaking and cooking classes. In the capital, Roseau, the recently upgraded Fort Young Hotel offers adventures including treks to waterfalls and lionfish hunting. Dominica is also the only country in the world where sperm whales reside year round – sightings are most common from November to March.

Elegant Resorts (01244 897581; elegantresorts.co.uk) has seven nights at Jungle Bay from £3,895 full board per person, including British Airways flights to Barbados departing London Heathrow on March 8, 2023, inter-island flights, transfers and activities.

“The Pitons are the eye-popping wonder in this Caribbean favourite.”

St Lucia’s iconic twin peaks, the Pitons, are the eye-popping wonder in this Caribbean favourite with the bonus that Gros Piton can be climbed in a couple of hours. The island would rank higher were it not one of the rainiest in the region, the flip-side being that its rich green interior is ideal for the cacao tree – the seeds of which are the chief ingredient in chocolate. Hotel Chocolat’s Rabot Estate has an excellent cacao-themed restaurant and hotel overlooking the Pitons while Sugar Beach enjoys a billion-dollar location sandwiched in between them.

Flights to St Lucia land at its southern tip, while most resorts are in the northwest. As a result the transfer provides a 90-minute scenic tour of this lush and mountainous island that offers plenty of adventures including hiking, biking and 22 dive sites. Unexpectedly, St Lucians have a love of country music (a legacy from the 1940s when there were two US military bases here) and their cuisine is a tasty fusion of French, British and Indian influences. New this winter is Kawabé Krawl, a collection of 12 bars dotted around the island that the tourist board has picked out for their authentic flavour.

Turquoise Holidays (01494 678400, turquoiseholidays.co.uk) has seven nights at Sugar Beach from £4,659 per person, including British Airways flights departing London Gatwick on March 19, 2023, transfers and breakfast. Book by October 31.

“British travellers are attracted to its easy-going style and a coastline fringed with 365 beaches.”

Antigua crowned the ‘Luxuries’ category, scoring well for its dependable five-star hotels such as Jumby Bay, Carlisle Bay and Curtain Bluff. It’s one of the easiest Caribbean islands to reach and this summer welcomed a record number of British travellers attracted to its easy-going style and a coastline fringed with 365 beaches.

New attractions for this winter seem well tuned to our tastes. The Antilles Stillhouse near Falmouth Harbour has introduced tours that demonstrate how it crafts its backyard gins flavoured with local sorrel and lemongrass, while the Antigua Vintage Teahouse on Fig Tree Drive brings a tropical twist to classic fare like Eton mess and Victoria sponge. English Harbour, on the south coast, is the most attractive base with its World Heritage-listed Nelson’s Dockyard and a waterfront bristling with classic sailing boats and constantly-polished superyachts. The adjacent national park has over 11 miles of hiking trails while the Sunday afternoon barbecue and party at Shirley Heights is a memorable spot to watch the sunset to the sound of live steel pan music.

British Airways Holidays (0344 493 0787; britishairways.com/antigua) has seven nights at Carlisle Bay from £3,289 per person, including flights from London Gatwick on March 9, 2023, and breakfast. Book by November 6. 

“It is home to more than 500 bird species – the most of any Caribbean nation.”

Birds are a key reason why this duo of islands makes our top ten, being home to more than 500 species – the most of any Caribbean nation.

Most British travellers only visit the small and peaceful isle of Tobago, which is easily reached on flights from London with Virgin Atlantic (until January 9, 2023) and British Airways. Here the star attraction is the Main Ridge Forest Reserve which has been protected since 1776 and has walking trails, along with Little Tobago, an offshore haven for birds near Speyside.

Port of Spain, the capital of Trinidad, is just a 25-minute flight south so a trip to both islands is feasible. Head there to see parrots, motmots and woodpeckers at the Asa Wright Nature Centre, 1,200 feet up in the northern mountains, which is due to reopen in December after a two-year closure. Geodyssey has a twin-island tour that visits this and the Caroni Bird Sanctuary, home to thousands of scarlet ibis, plus a garden where you can spot up to 14 species of hummingbird. Trinidad’s world-famous carnival will hit the streets on February 20, 2023, while British Airways introduces a direct service from London Gatwick to Port of Spain on March 26, 2023.

Geodyssey (020 7281 7788; geodyssey.co.uk) has a private 14-day ‘Trinidad & Tobago Odyssey’ from £4,440 per person, including flights from London Gatwick departing January 20, 2023, accommodation, all transport, guided excursions, breakfast and nine lunches.

“Top of the to-see list should be the Blue Mountains, a dramatic range of lofty peaks.”

This spectacular island has much more to offer than its numerous all-inclusive beach resorts, a concept born here in 1978. Top of the to-see list should be the Blue Mountains, a dramatic range of lofty peaks north of Kingston that produces sublime coffee – for an introduction visit the Craighton Coffee Estate near Irish Town which has a Great House dating from 1805.

Jamaica’s capital offers insights into the story of reggae at its Bob Marley Museum, where your tour guide may well burst into song, and other rewarding stops are Port Antonio, famous for its jerk stalls, and Negril with a four-mile beach that catches the sunset. Explore offers a small group tour that bundles these together along with forest hikes, river-rafting and – new for this season – some time in Charles Town where the descendants of freed and escaped slaves maintain their distinctive culture.

Explore (01252 883101; explore.co.uk) has a nine-night ‘Explore Jamaica’ group tour from £2,259 per person departing Kingston on February 6, 2023, including accommodation, transport, activities and breakfast. Flights are extra. British Airways (ba.com) flies from London Gatwick to Kingston from £653 return.

“Britain and Barbados share a mutual love of cricket, churches and gardens.”

The easternmost island in the Caribbean is a firm favourite with British travellers for good reason: we’ve been visiting its gentle shores since 1625 and share a mutual love of cricket, churches and gardens. Barbados is also the birthplace of rum, has a thriving restaurant scene and – as our survey reveals – gets top points for its density of five-star hotels. Long-established flagship properties on the west coast, such as Sandy Lane, Coral Reef Club and Cobbler’s Cove, have set a benchmark for civilised luxury by the sea that attracts a well-heeled band of regulars every winter.

Barbados also scores well on the Human Freedom Index, which assesses the degree of civil liberty in a nation, and the 2022 Environmental Performance Index that monitors achievements in sustainability. Few visitors are aware of the island’s impressive ‘green’ side, which is manifest in the excellent free hikes organised by the Barbados National Trust, the biodynamic PEG Farm with camping and a superb restaurant, and regeneration projects such as Walkers Reserve, Coco Hills Forest and the Barbados Trailway.

Tropic Breeze (01752 880880; tropicbreeze.co.uk) has seven nights at Tamarind by Elegant Hotels from £2,745 per person all-inclusive, including British Airways flights from London Heathrow on December 11 and transfers.

“Scenic versatility includes tropical rainforest, arid desert and a profusion of glorious beaches.”

The Dominican Republic is home to the highest and lowest points in the Caribbean – the 10,174ft Pico Duarte, which can be climbed on a two-day trek, and Lago Enriquillo, which lies 151ft below sea level. This scenic versatility, which includes tropical rainforest, fertile valleys, arid desert and a profusion of glorious white-sand beaches, is reflected in a top score for biodiversity.

Nature-related adventures include admiring humpback whales on the Samaná Peninsula, white-water rafting on the Río Yaque del Norte and trying to spot 31 unique bird species such as the Hispaniolan woodpecker.

Holidays from the UK are principally geared to the fly-and-flop market using direct services from London Gatwick to the beach resorts of Punta Cana, on the eastern tip of Hispaniola, with British Airways and Tui (the latter also fly from Manchester). On the south coast, Santo Domingo, the capital, is a popular port of call for Caribbean cruises with a compelling heritage dating back to its founding in 1496 by Bartholomé Columbus. Even here, amongst its monumental churches and fortifications, nature’s splendour shines through at Arroyo Hondo, the largest botanical gardens in the Caribbean with an arboretum containing 1,500 trees.

Tui (020 3451 2688; tui.co.uk) has seven nights at Impressive Punta Cana from £1,616 per person all-inclusive, including Tui Airways flights from London Gatwick to Punta Cana departing February 12, 2023, and transfers.

“Magnificent Pink Sands Beach is one of the best in the Caribbean.”

With its 700 islands and 2,400 cays stretching south east from Florida for 760 miles, The Bahamas easily tops our Natural Wonders category and also has the lowest population density of the contenders. Even more impressive is its 32 national parks – more than double its closest rival.

To make the most of a trip to this affluent archipelago, which was a British colony for 325 years, it’s essential to travel beyond the gateway island of New Providence, dominated by the cruising hub of Nassau. A 30-minute flight east, Eleuthera is a narrow, 110 mile-long island with pineapple farms, surfing spots and a tranquil vibe. Alternatively, join the partying on Harbour Island, just a five-minute water-taxi ride from North Eleuthera airport. This is the quintessence of the small, moneyed Bahamas escape with smart hotels, classy restaurants and the magnificent Pink Sands Beach – one of the best in the Caribbean.

Bon Voyage (0800 316 0194; bon-voyage.co.uk) has seven nights at Valentines Resort on Harbour Island from £3,795 per person room only, including British Airways flights from London Heathrow to Nassau on November 5, inter-island flights, ferry transfer and golf cart rental.

“Cuba has an atmosphere like nowhere else, born out of revolution and reflected in faded grandeur.”

Cubans have many talents – music, dancing, rolling cigars and just getting through the day in a state-run economy recently whacked by Hurricane Ian. Form-filling is clearly another, judging from the surprising fact that the largest country in the Caribbean boasts nine World Heritage sites, plus another three on Unesco’s ‘tentative’ list, which is by far the greatest tally in the region.

This is one reason it’s made it to the top of our survey as the greatest Caribbean island, plus the fact that it tops the closely-contested ‘Experience and Environment’ category. Oh yes, Cuba has an atmosphere like nowhere else, born out of revolution and reflected in its glossy vintage cars, seductive soundtrack and the faded grandeur of its Spanish colonial cities. Cuba is also safe, with one of the lowest crime rates, and being 750 miles long it offers plenty to enjoy from the nightlife of Havana to horse riding in Viñales and diving the clear waters off Isla de Juventud. The island’s political and economic isolation has an obvious impact when it comes to luxury spas and fine dining, but it makes up for this by delivering a Caribbean experience like no other.

With no sign that Virgin Atlantic will reinstate its pre-pandemic flights to Havana, the only direct route to Cuba is aboard Tui’s charter flights from Manchester to the beach resorts of Varadero; fares from £749 return. Intrepid Travel, which has been running small group tours here for over 15 years, recommends travelling via Madrid. This winter the operator has introduced a ‘Premium Cuba’ tour visiting four cities with a salsa lesson and ride in a classic car included. Note that UK travellers who visit Cuba may not be eligible for the United States’ Esta visa-waiver programme, and could instead need to apply for a more expensive tourist visa that requires a trip to a US embassy.

Intrepid (0808 274 5111; intrepidtravel.com) has an eight-night ‘Premium Cuba’ group tour from £2,561 per person departing Havana on March 18, 2023, including accommodation, transport, activities, breakfast and some meals. Flights are extra. Air Europa (aireuropa.com) flies from London Gatwick to Havana via Madrid from £698 return.