Caribbean: The perfect 10

1. St Barts & St Martin: A tale of two islands

'Puddle jumpers' are coming in over the bay. For tiny twin-prop planes, they aren't short of noise but I'd wager the sound system banging out zouk (Guadeloupean carnival music) is winning. I'm eating rice and peas with johnny cakes and the bass is bouncing these fried cornbread spheres across my plastic plate like popcorn in a pan.

As the sun sets on St Martin, things are hotting up. Outside Talk of the Town, one of the lolo food shacks lining Grand Case Bay, a crowd is gathering. The beach-tousled and barefoot punters pad in off the sands, gathering in swaying groups around roadside speakers, beer in one hand, flip-flops in the other.

I pay up, parting with around a tenner (two beers included) and make for the beach, stepping over a mass of cables where a band is setting up on the sand. Next to the bay's crumbling pier, a group of teens climb aboard a ferry, only to hurl themselves off the top deck into the sea.

If you've come from the pristine, packaged resorts of neighbouring St Lucia or Antigua, the beachfront at Grande Case, flanked by peeling-paint restaurants with names such as l'Atlantique and Le Cottage, feels like a faded fantasy of Aznavour-era St Tropez. Yet their kitchens are stocked with produce flown in daily from Paris. Bien sur. And while St Martin receives the delivery first, you can bet St Barts gets the choice cuts. It's less than 10 minutes by puddle jumper to St Martin's exclusive neighbour. The island's 640-metre runway, sandwiched between a cliff and a sunbathers' beach, is a YouTube sensation ('the world's most dangerous runway!'), thanks to the white-knuckle ride landing here it can entail. Grocery stores here stock Champagne and foie gras and paparazzi decamp in winter to snap A-listers on yachts. I hope to spot a few during my stay at Eden Rock — 'Ultra Beach Villas' here start at £20,000 a night.

In Corossol, one of St Bart's few traditional fishing villages, I buy a bag woven from dried lataniers (palm leaves) from an old woman. Her shutters are open, framing fishing boats, sand and the sea, stretching west to St Eustatius and Saba islands. The only sound is the rustle of palms, the chink of spinnakers and her chatter. Until, that is, a puddle jumper buzzes overhead and I can't help but wonder what prized goods it's carrying. Words: Sarah Barrell

How to do it: Carrier offers seven nights from £2,905, including one night, B&B, at La Samanna, St Martin, and six at Eden Rock, St Barts, with breakfast, one lunch or dinner, wine on arrival, a rental car, sunset cocktail, return economy British Airways flights from Gatwick to Antigua, inter-island flights with Tradewind Aviation and transfers. carrier.co.uk

2. Monserrat: The Pompeii of the Caribbean

The warped, dying trees are stripped of their leaves and choking in the ashy maelstrom. The grey dust coating the Belham Valley, turning it into a sinister beach of decay, is whipped into an eerie cloud by the slightest breeze.

This was once a place of golf courses, luxury accommodation and lush greenery. But the monster looming to the east changed all that. Between 1995 and 1999, the Soufrière Hills volcano erupted repeatedly. Two-thirds of the island, once the wealthiest in the Caribbean, had to be evacuated. Over half of the islanders decided to start a new life elsewhere, leaving around 5,000 to forge new homes in the hilly northern patches once thought fit only for goats.

If you take a trip up to the Montserrat Volcano Observatory, where a multinational team of scientists still monitors Soufrière Hills, you can learn about the eruptions and consequent disruptions. But this is an island of amateur volcanologists. Pull up a barstool, and someone will tell a tale of losing everything and sleeping in what amounted to refugee camps. Almost all the stories are told not in sadness, but with good humour and positive visions of the future.

Montserrat is an island of rocky, black sand coves rather than sunbed-dotted white beaches; of small guesthouses rather than resorts; of gently ambling over ridges and down valleys rather than being bussed around cruise passenger-swarmed tourist attractions.

It's as low key as the Caribbean gets, yet it's one of the most extraordinary places on earth. The frog-in-your-throat impact of seeing the Belham Valley's burial builds as the taxi struggles out of it and along the furiously bumpy track up to Garibaldi Hill.

At the top, I get out and peer down at what lies beneath. Here, under a deluge of mud and ash are the remnants of Plymouth, Montserrat's capital. A new one is slowly being built in the north of the island, but the church steeples and occasional rooftop sticking out of the abandoned city are a chilling reminder of what succumbed to nature's ferocity. It's a small-scale, modern-day Pompeii, taken in from a lonely observation point where the birds no longer sing. And the vision stays seared in the mind long afterwards. Words: David Whitley

How to do it: Virgin Atlantic flies to Antigua from £547, and regular ferries connect to Montserrat (visitmontserrat.com has timetables). Stay at Gingerbread Hill (volcano-island.com) from $48.15 (£31.35). Tours are best arranged informally through Gingerbread Hill. virgin-atlantic.com

3. Cuba: Hit the revolutionary trail

There aren't many men I'd follow up a mountain — especially one on the other side of the world, with a guerrilla camp at the top. But then, this isn't any old bloke we're talking about; it's 'El Che' (rough translation: 'The Dude') — as the locals call him; Ernesto 'Che' Guevara to you and I.

Che Guevara apologist I'm not, but I've always been intrigued by the beatific face that launched a million T-shirts. And, travelling around Cuba, I've been galvanised by the revolutionary propaganda daubed on every dusty corner between Havana and Santiago. When it comes to the cult of personality, Fidel Castro barely registers. Conversely, El Che is represented with an almost religious fervour.

In Santa Clara, the town Che is most associated   with (his 1958 victory there allowed Castro to take Havana), I visit his tomb. Here, atop a concrete pillar, a huge bronze Che in combat gear and brandishing a rifle, improbably, moves me to tears. When, in Bayamo, I learn the Cuban Revolution had begun from a hideout on a nearby mountain, Pico Turquino, I make straight for the trailhead — 3,116ft up, with jungle-clad peaks all around, a sliver of Caribbean Sea below and Jamaica a dark line on the horizon. Even from up here, it's a slog to La Plata, which Castro called his 'best loved' camp — an hour up and down past wild pigs, mules, pygmy owls and hummingbirds. The sun blazes through pines, palms and thick foliage (there are 450 types of fern).

Suddenly, a hut swaddled in palm fronds emerges out of the undergrowth: Che's 'hospital'; a rusting lantern still swinging from a rudimentary beam. Che was a trained doctor, but preferred to work on revolutionary radio, says Jorge, my guide. In the next hut sits his original broadcasting equipment — along with Fidel's fountain pen and pair of trousers.

Sixteen more huts perch over a nearby gully. Jorge walks me through a dorm, storeroom and kitchen; its cupboards stocked with equipment abandoned by the rebels. Teetering over the gorge, surrounded by bullet hole-riven trees, is the one place I'm not allowed to set foot in: Castro's hut, complete with bed, desk, kerosene-powered fridge and ensuite privy. I ask why Fidel lived so much more luxuriously than the others. "He was the leader," says Jorge, looking astonished. But as we start the slog back, I'm thinking it's no wonder it's man-of-the-people El Che — not luxury-loving Castro — whose legend lives on. Words: Julia Buckley

How to do it: Journey Latin America offers an 11-day tailor-made Cuba itinerary, including Santa Clara, Bayamo and La Plata, from £3,690 per person including flights, accommodation and most meals. journeylatinamerica.co.uk

4. Tobago: Sleepy charm

Englishman's Bay does not look very English. Forest, thick with branches and leaves, swarms almost to the water's edge. The beach is perfectly shaped — a curve of mathematical purity that might have been drawn on a blueprint by some divine architect. The sand is the dark brown of demerara sugar. Observing all this in the fledgling light of early morning, with the chill of the night still on the air, I'm sure I've found the ideal image of the Caribbean that's so common in holiday brochures, yet tougher to source in reality.

But then Tobago specialises in such snapshots. Englishman's Bay is just one of several coves (Parlatuvier Bay and Bloody Bay are two others) dotted along its north coast that's as remote as it is beautiful, bereft of much in the way of development, noise or modernity.

In part, this is down to location. Tobago is the forgotten child of the Caribbean — pitched so far south west, it's nearly lost in the shadow of South America. Only Trinidad, Tobago's sibling in statehood, lies closer to Venezuela — and the relationship is a strange one. Blessed with rich oil and gas deposits, Trinidad toils in the sun — pausing only to cast tired glances at Tobago, which snoozes under palm fronds 30 miles to the north east. Of course, Tobago's sleepiness is key to its charm. And the island's unhurried appeal plays out visibly at its southwest tip. The main resorts are clustered here, notably around Pigeon Point, Crown Point and Store Bay — where locals and tourists sip bottled beer together at shack bars on the beach. The theme continues in nearby Scarborough, where island-capital status does not translate into urban cacophony. When I wander through the daily market, filling a bag with papayas and mangoes, the ambience is relaxed and quiet.

But even this seems like a riot compared with the east of the island. Tobago Main Ridge Forest Reserve is a slice of natural wonder, where kingfishers and hummingbirds flit in the canopy. Then there's Speyside, where divers explore the depths of Batteaux Bay, and Jemma's Seaview Kitchen — a restaurant built around the boughs of trees on the shore — which is true to its name. As I devour a bowl of spicy shrimp while staring at the ocean, I can't be certain — the whirr of the generator aside — what century it is. Words: Chris Leadbeater

How to do it: A seven-night stay on a B&B basis, including flights from Gatwick, costs from £599 per person. dialaflight.com

Read more in the Nov/Dec 2013 issue of National Geographic Traveller (UK)