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Sint-Maarten/ St Martin
If wanting to double dip on the Caribbean's rowdy and sophisticated sides, this island weirdly split between Dutch and French control is the place. Sint-Maarten – the Dutch side – is a popular cruise ship haunt, and capital Philipsburg has more than its fair share of party bars. The French side, however, is much more demure. The best beaches can be found here – Orient Bay is nudist-friendly, while Baie Longue has the sheer gorgeousness. Head to Grand Case for food – some of the Caribbean's best restaurants cluster within a couple of blocks of each other. Stay at chic celeb hangout La Samanna (pictured, see belmond.com/la-samanna-st-martin) from $680.
San Juan – in particular the colonial-looking, rum bar-filled and fortress-flanked Old San Juan section – is the most enjoyably evocative city in the region. But beyond the city, the island's just big enough to pack a variety of adventures in. Kayaking Puerto Rico (kayakingpuertorico.com) runs night paddling tours on Laguna Grande, otherwise known as Bioluminescent Bay due to the micro-organisms in the water that light up when touched. Other day trip options include the world's largest radio telescope at the Arecibo Observatory and the humungous Bacardi factory. Stay on San Juan's best beach at the Intercontinental from $195 (intercontinental.com/Puerto-rico).
With a cultural impact far outweighing its size, Jamaica has an unmatched intensity and sense of feistiness. Lock yourself away in the bland resorts around Montego Bay or Ocho Rios, and you won't feel it, but hippyish Negril in the west has more of a beats-on-the-beach flavour and Portland in the east is green and mountainous – home of both the best rafting trips and best jerk chicken. Climbing the Dunn's River Falls is practically obligatory while, due to geographical oddities, the Appleton distillery tour is the Caribbean's most fascinating rum outing. Stay on the Negril clifftops at the Rockhouse from $115 (rockhousehotel.com).
Dominica flips the Caribbean sun and sand stereotypes on their head, and the beaches are frankly rubbish. It doesn't matter, though – the diving and hiking scenes make up for it. The mountainous interior shoots up pretty much straight from the sea, with trails of varying thigh pain weaving through lush National Parks. The hike through volcanic fields to the Boiling Lake is the most distinctive leg-sapper. This is also the island with the biggest indigenous presence. The Touna village (kalinagoterritory.com) offers a chance to explore the almost extinct Carib culture. Stay in the Jungle Bay Resort's wooden cottages from US$480. See Junglebaydominica.com.
If ever the Côte d'Azur and the Caribbean were to interbred, it'd look a lot like St Barths. A tiny overseas chunk of France, this is where the impeccably well-dressed and outrageously loaded like to compete for chic points. Rocky terrain leads down to a few good beaches, but St Barths is very much about who can show off the swankiest villa and who can moor the most impressive yacht in the marina. Cottages at Eden Rock, consistently voted one of the top 100 hotels in the world, cost from 600 euros. See edenrockhotel.com
Get there before it changes has been the catch-cry for about three decades, and in truth, Cuba has already changed. But the gorgeous colonial buildings of Trinidad evoke Latin America rather than sanitised island getaways, the salsa clubs of Havana still have the steaminess and the revolutionary oddities such as Che Guevara's mausoleum still have pride of place.
It's arguably the only Caribbean island worth tackling on an organised tour, and G Adventures runs a 15-day Colonial Cuba highlights reel for 1019 euros. See gadventures.com
The writer has been a guest of the Puerto Rico, St Martin, Sint Maarten, Dominica and Jamaica tourist boards.