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Where to go in the Caribbean for the first time, and off-the-beaten track islands

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Your first time in the Caribbean?

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Palm trees, white-sand, an umbrella-swizzled cocktail… Sure, that’s the brochure view of the Caribbean. And if sipping rum from a coconut is what you’re after, these tropical islands will deliver. But more than 20 countries make up this sun-soaked region, each with its own culture, quirks and flavours. Take time to choose the right piece of paradise for you.

The region stretches from Trinidad & Tobago – a stone’s throw from the Venezuelan coast – north to the Bahamas and is, by and large, seaside holiday heaven, its beaches exquisite, the laid-back vibe infectious.

But which island to choose? Temperatures are broadly similar year-round, never moving much outside the blissful 25-30°C bracket, with rain ("liquid sunshine") falling fairly frequently, but a bit less so December-April. There’s the hurricane season to consider: officially June-November, with the worst storms usually occurring from mid-August to October. The southernmost islands – such as Trinidad & Tobago, Barbados and Grenada – sit below the so-called hurricane belt and are less likely to be troubled (though nothing is guaranteed). July and November can be good months to pick up off-season bargains.

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For Caribbean first-timers St Lucia is a lovely choice. English-speaking, left-hand-side driving and served by direct flights from the UK (around nine hours), it’s one of the region’s most naturally beautiful islands: largely rural, heavily rainforested, volcanically rumpled. Most of the development is in the north, especially along the western coast, between Pigeon Island (site of an 18th-century fort) down to capital Castries. The south, where you’ll find the emblematic twin peaks of the Pitons, is sparsely populated and gorgeously green.

Sugar beach sits beneath St Lucia's Pitons (Photo: AFP/Getty)

The nature of St Lucia means it has something for most types of holidaymaker. Honeymooners can find privacy in high-end hotels and restored plantations – for example, the secluded cottages at historic Fond Doux estate, which overlook the Pitons (doubles from $189/£145). Families will find plenty of diversions, from snorkel and boat trips to jungly zip-wires to messing about at the Splash Island Water Park or finding out about chocolate - and making a bar - on Hotel Chocolat’s Rabot estate. For the adventurous, there are hiking and mountain-biking trails, sulphur springs to dip in and opportunities for sailing, SUP-ing and diving – not least the 10m-deep wreck of the Lesleen M. Sporty types could stay at The BodyHoliday, where not just food and drink but all manner of exercise classes, activities and spa treatments are all-inclusive; Destinology has one-week packages from £1,820pp.

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Inside track: St Lucia beyond the beach

“Spend time exploring St Lucia. Head to the south, to the Tet Paul Nature Trail. You get the best view of both Piton mountains from here. The trail is an easy amble up the hill and along the way you can walk through the organic farm that the local community tends. Look out for the Stairway to Heaven and then you've reached the platform at the top for the most stunning panoramic view across the island and out to sea.” - Patricia Charlery-Leon, Director of SLTA UK and Europe

Off-the-beaten track options

If you find the Caribbean as intoxicating as its ubiquitous rum punch, you’ll probably want to return for another hit – perhaps with an alternative angle.

Dominica is a good example. The wild “Nature Isle” defies timeworn images of Caribbean islands by proffering mountains, rainforest, waterfalls and a distinctive culture rather than fly-n-flop resorts – indeed, while Dominica has good beaches, many have black sand. You come to Dominica for something different; for a more authentic immersion in the tropics.

Pigeon Point, Tobago (Photo: Visit Tobago)

It’s more than two years since Hurricane Irma ravaged the island and recovery is underway. The opening or revamping of some prestigious properties – such as Jungle Bay and the Kempinski Cabrits – is a good sign. These add further depth to the island's varied accommodation offering, reinforcing that it’s one of the best Caribbean islands for those on all budgets. You can go cheap-rustic in a forest cabin (try Hibiscus Valley) or splurge on eco-luxe (like secretbay.dm).

Read More:

Tobago's wildlife glitters at every hour

Despite the devastation of Irma, no other Caribbean island can compete when it comes to hiking – Dominica’s Waitukubuli Trail remains the Caribbean’s only long-distance hike and the Boiling Lake Trail is arguably the region’s greatest day-hike. New for 2020, an official Hiker’s Log Book and Passport has been launched, encouraging walkers to record their adventures. Also new, Hike Caribbean is offering a five-night Eco-Friendly Dominica package from £989pp.

Tobago's Main Ridge Forest Reserve (Photo: Visit Tobago)

Tobago has a wild edge, too. Despite being accessible by direct flights from the UK, it remains remarkably untouched by mass tourism. Many hotels are small-scale and family-run and the tone feels authentically Caribbean. The dazzling beach at Pigeon Point might get crowded, but elsewhere the idyllic white sands remain peaceful. Tobago is also brilliant for birding, from the hummingbird-buzzed Forest Reserve (one of the world’s oldest protected rainforests) to Little Tobago, an uninhabited isle where boobies and red-billed tropicbirds gather, and turtles fin offshore. Contact Newton George, Tobagonian birder extraordinaire, who runs tours. Just Tobago arranges all types of holiday here; its Tobago Trio, including five nights each in the west, south and wilder north, costs from £1,960pp. For an eco-treat, stay in a treehouse-style cabin at Castara, where guests are encouraged to get involved with the community (doubles from £105).

Inside track: hiking Dominica

“Stubbornly off the beaten path, Dominica is replete with hiking trails, pristine coral reefs, sleepy villages and coastal waters so deep that whales reside here year-round. Also living here are the Kalinago – descendants of the region’s first people who eke a living from traditional bushcrafts such as canoe-building and basket-weaving. Culture and nature combine to deliver something offbeat to travellers who seek unforgettable adventures.” - Paul Crask, Editor and Publisher of Dominica Geographic magazine, author of the Bradt Travel Guide to Dominica

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