How to choose a Caribbean island

The ultimate tropical getaway, the Caribbean conjures images of palm-fringed beaches, rum-fueled dancing and lush jungle excursions. Pick any of the 700-odd islands that form an arc between Florida and Venezuela and you’ll get all these things and more.

Rich in African culture brought to the region by the trade of enslaved people, the islands are also steeped variously in British, Spanish, French and Dutch heritage, making the Caribbean one of the most culturally diverse places on the planet and lending each island its own idiosyncrasies. 

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It’s to be expected, then, that you find yourself in the same position as Christopher Columbus, who wrote in his journal in 1492: “I saw so many islands that I hardly knew…to which I should go first.” Whether you’re looking for a party city or a family-friendly destination, we’ll help you decide where to go. Here are the eight best places to visit in the Caribbean.

1. Antigua

Best for beaches

Boasting a beach for each day of the year, low-lying Antigua in the Leeward Islands delivers a multitude of postcard-perfect beaches, with coral reefs just a flipper-kick from shore. Depending on where you are, the hue shifts from brilliant white through rose gold to cotton-candy pink. 

Choose between a beach lined with lively bars blaring out soca tunes, or a near-deserted strip of sand where it’ll be just you and the odd pelican diving for fish. If you want to join picnicking locals, head to Jolly beach on the west coast; for solitude, try Half Moon Bay in the southeast, and for tree-shaded golden sands, head to Pigeon Beach on the edge of Falmouth Harbor. 

The World Heritage Twin Pitons are framed by sunlit flowers in the early morning. Focus on flowers, with Pitons fading into background.The iconic twin Pitons are St Lucia’s most photographed attraction © Getty Images

2. The Pitons – St Lucia

Best for hiking

These iconic twin peaks are St Lucia’s most photographed attraction, which isn’t surprising, as they tower more than half a mile above sea level and can be viewed from as far north as the capital Castries.

Gros Piton, the largest of the peaks, is the one to scale (Petit Piton has near-vertical slabs and climbing is restricted). Start at sunrise and you’ll be at the top before the heat of the midday sun. January, February and March are great months to visit because the soil will be dry. 

Wake to an up-close view of these verdant volcanic plugs by staying at Ladera Resort, which offers rooms that are completely open to the rainforest.

Planning tip: Book a guide from Gros Piton Tour Guides Association and you’ll not only make it to the summit without losing the path, you’ll also learn the history of Fond Gens Libre, a settlement that played an important role in the 1748 slave rebellion (and the hike’s starting point), and find out about the flora and fauna of the rainforest you pass through. 

Old sign of the Lafayette restaurant and bar in the Old Havana districtWander the narrow streets and admire the architecture in Habana Vieja © Getty Images

3. Habana Vieja – Cuba

Best old town

The most populated and most visited city in Cuba and one of the best cities in the Caribbean, beguiling Havana is associated with Hemingway and Cadillacs, music-filled theaters and grand rum bars.

The Havana you’re looking for is the old town, known in Spanish as Habana Vieja, where you can wander narrow streets, admire the architecture of restored Spanish buildings, stop to listen to a street-side salsa or son band and dip in and out of the various museums, churches and palaces that make up this Unesco World Heritage Site. 

The city hums in the day, but at night it’s all-singing, all-dancing. To soak up the vibe head to Plaza Vieja, pull up a chair on the terrace of one of the many bars and cafes and be entertained by roving bands. Then head to the 200-year-old bar El Floridita, where Ernest Hemingway famously knocked back daiquiris after a day at the typewriter. 

4. Bonaire Marine Park

Best for snorkeling

Bonaire is the B in the Dutch ABC islands and lies to the east of Aruba and Curacao, just off the coast of Venezuela in the southern Caribbean. Something of a trailblazer, the island turned its entire coastline – and that of neighboring Klein Bonaire – into a 6400-acre marine park in the late 1970s.

The island has about 90 dive and snorkel sites where you can explore the protected underwater world, mostly situated among the sheltered coral reefs off the west coast. This is a good place to visit in July, because it is south of the hurricane belt. 

Planning tip: Divers and snorkelers must pay the marine park nature fee, which is $25 for non scuba and $45 for scuba divers and is valid for a year. You can purchase it directly from the National Parks Foundation.

5. The Grenadines

Best for sailing

An archipelago stretching 60 miles from St Vincent in the south to Grenada in the north, the Grenadines feel remote and largely untouched by tourism – a far cry from the commercialization of the US or British Virgin Islands.

With the challenge of occasional strong Atlantic winds and the reward of calm waters on deserted beaches (minus the odd rum shack), this is some of the best sailing in the world for the competent sailor. Passages between the islands only take an hour or two, so you’ll get plenty of downtime too.

Planning tip: This is a good place to visit in July, August, September or October, because it’s south of the hurricane belt. Start your charter in St Vincent and finish in Grenada for an easier sail. Easterly trade winds make it harder to sail north up the chain. 

6. Inagua – The Bahamas

Best for wildlife lovers

The southernmost island group in the Bahamas is made up of two islands. Despite its name, Great Inagua only has a population of about 1200 people, but its flamingo population exceeds 80,000 birds, flocking around aptly named Lake Rosa. And Little Inagua is the largest uninhabited island in the Caribbean, becoming a national park in 2002.

These remote islands are a haven for ecotourism, and visitors come to see the flamingos, parrots, pelicans and 140 other native and migratory birds that can be spotted here.

Planning tip: Travel by mail boat from Nassau, which is 320 miles northwest, or fly into Great Inagua airport. To visit Little Inagua, a nesting ground for endangered sea turtles, you’ll need to ask a fisherman to take you by boat. The best time to see the turtles hatching is between August and September. 

Tourist learning to windsurf at a busy Punta Cana beachPunta Cana is one of the best places for a family holiday in the Caribbean © Getty Images

7. Punta Cana – Dominican Republic

Best for families

The glut of family-friendly hotels that hug the “coconut coast” on the east of the Dominican Republic make this one of the best places to go if you’re looking for a family holiday in the Caribbean. The childfree may want to actively avoid the area, because it’s more built up than other Caribbean coastlines, but if it’s an all-inclusive hotel with a waterslide you’re after, then you’ll find no shortage among the popular brands jostling for attention. 

Whether you want five-star luxury, such as that found at Bahia Principe Fantasia Punta Cana, which has a fairytale palace astride the swimming pool, or the recognizable cartoon characters found at the Nickelodeon resort, you’ll find a hotel to please the whole family. 

8. San Juan – Puerto Rico

Best for partying

Wherever you are on the US Commonwealth island of Puerto Rico you’re never more than a couple of hours by car from San Juan, the island’s capital. Which means there’s no excuse not to spend at least one night of your holiday partying Puerto Rico style. A night out in San Juan is a raucous affair, generally centered around the old town, which has the highest concentration of bars and clubs. 

You’ll find piña coladas served until the early hours, but not in La Factoria, which is taking the island’s mixology to the next level (and often features on lists of best bars). Here you can try signature cocktails such as the lavender mule, made with ginger tea, lavender cordial and Ketel One vodka.

For a street-party vibe, head to La Placita de Santurce, which by day is the location of the fruit and veg market and by night filled with the sounds of salsa. This is one of the best places to visit in the Caribbean in December or early January because the Christmas period (from December 15 to January 6) is even more of a party than usual. 


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