The 10-Point Caribbean Escapes Plan

With more than 30 major islands to choose from — from the lush wilderness of Dominica to the desertlike terrain of Curaçao — the Caribbean can be almost all things to all people. Want a back-to-nature hiking experience? You got it. Want to be pampered in a five-star resort where the staff-to-guest ratio runs at two to one and the toughest decision you will make each day is whether to have a hot stone or an ayurvedic massage? No problem. Or do you just want to chill at a place where there’s no TV, no cellphone service and where dinner is no more elaborate than the catch of the day? Consider it done.

But choosing the right Caribbean vacation is not as simple as blocking out the dates and going online to find the best airfares — for the infinite possibilities of the Caribbean can cut both ways.

You can end up with the trip of a lifetime or a vacation from hell. Just ask a newly married couple who have planned a romantic getaway only to find themselves sharing the pool with dozens of screaming children, or the adventure-seeking windsurfer who has ended up on the windless side of the island, or the party animals who didn’t realize that the hot spot they had heard so much about is already so last year.

That’s where this guide comes in — a 10-point primer on some of the best island getaways, geared to the kind of vacation you might want to take this winter, whether it’s a week filled with nonstop golf or an escape to a remote island that feels all your own. Just one thing: Don’t forget your passport. Americans are now required to carry one for air travel within the Western Hemisphere including the Bahamas, Bermuda and the Caribbean (except for the Virgin Islands and Puerto Rico). You don’t want your trip to end even before it starts.

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Guide to Tobago

So much more than simply another Caribbean island in the sun, Tobago offers a wealth of reasons to escape winter in Britain. Little sister to Trinidad and, thankfully, still relatively untouched by developers' claws, the island is home to picture postcard-perfect beaches (complete with obligatory palm trees), pristine coral reefs, and an abundance of flora and fauna - as well as the oldest protected rainforest in the western hemisphere.

Tobago, which takes its name from the Carib word tavaco (originally meaning a pipe, then tobacco) also has shack-loads of charm. The ease and pace of Tobagonian life hits you the minute you step off the plane and snake slowly towards immigration - a tiny, scruffy two-roomed affair, utterly unprepared for the arrival of a jumbo jet. Yet, sedately, officials rubber-stamp 400 passports, endearingly greeting each traveller with a grin.

The dimensions of Tobago, 41km long and 12km wide, are uncannily close to those of the Isle of Wight. But Tobago has the advantage of lying just 11 degrees north of the Equator. The island has the Caribbean Sea on its leeward (western) side and the Atlantic Ocean on its windward (eastern) shores. And very different they are, too.

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Buenos Aires - Argentina

Tour-guides like to give Buenos Aires the nickname "Paris of the South". It is, they claim, a smouldering city of tango, barrios and avenidas; a rambling metropolis with sufficient elegance and sophistication to (almost) be European.

On the face of it, the tour guides have a point. Argentina's capital boasts a colourful history; it's got magnificent architecture and culture, together with first-rate shopping, and a lively night-time "scene" to rival any destination on the cosmopolitan traveller's hit-list.

Yet scratch below the surface, and BA offers a very different insight into the land of the gaucho. Every now and then, amid the steak and Merlot and hazy afternoons, the porteños, as locals are known, will provide adventurous travellers with a glimpse into the dirty, chaotic heart of Latin America.

That, at least, was the theory that persuaded my brother and me to hop on to a 14-hour flight across the Atlantic to witness the twice-yearly football match they call El Superclasico. This magisterial name - not just "super," but "classic" too - denotes one of the legendary meetings between the city's biggest clubs, Boca Juniors and River Plate.

Each Superclasico provides an occasion for Buenos Aires to celebrate one of the greatest club rivalries in world football, a fixture that has showcased the exquisite talents of such sporting legends as Batistuta, Palermo, and the maestro himself, Diego Maradona.

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Espiritu Santo Island - Mexico

The wind is getting stronger and the waves higher. As a sailor I can recognise the brisk little squalls charging across the surface of the sea; if I was in a boat, this would be fun. But I'm in a sea kayak. As it's only 14 inches deep, I'm not so much on the water as in it.

This is the first day of a four-day trip up the west coast of Espiritu Santo Island, just off Mexico's Baja California in the Sea of Cortez, and only my second day of sea kayaking ever. Thankfully we have already practised "wet exits", the art of banging on the hull of an upturned kayak before pulling off the sprayskirt to swim out of the cockpit.

The technique is a useful one; beginners can find an eskimo roll, a common method of righting kayaks, tricky in sea-going models. All the same, I'm relieved when we eventually make it to the beach where we will camp for the night.

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Choquequirao - Peru

Peru. Say the name and your imagination will no doubt conjure up the country's geographical wonders, perhaps its recent history of political turbulence and its lost cities. It has long attracted travellers, explorers and treasure hunters, united in their search to uncover the secrets and wealth of ancient civilisations. Indeed, only last year the German explorer Stefan Ziemendorff discovered the third tallest free-falling waterfall in the world in the Amazonas region of Peru; the Gocta Waterfall measured a dizzying 771m high.

What seems remarkable is that in this age of satellite imagery such a vast waterfall had lain undiscovered. But then this is what has attracted thrill-seekers to deepest Peru since the Spanish Conquistadores first set foot here. It was a spell under which I fell 15 years ago.

The early 1990s were not a good time for Peru. The country was plagued by guerrilla warfare waged by the Sendero Luminoso. The aim of this Maoist group, whose name translates as Shining Path, was to replace the Peruvian bourgeoisie with a revolutionary peasant regime. The Sendero Luminoso also engaged in armed conflict with Peru's other major guerrilla group, Tupac Amaru Revolutionary Movement (MRTA). Peru was a war zone: for a wide-eyed gap-year student with an unhealthy interest in Kate Adie and Don McCullin and a thirst for excitement and adventure, it was the perfect place to explore.

For four memorable weeks, I travelled with friends the length and breadth of the country, from the high Andes to the low Amazon. Fresh from six months in tourist-friendly Ecuador we felt like pioneers exploring a new land.

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Cycling in Costa Rica

The compact Central American nation, sandwiched between Nicaragua and Panama, is already well known as a magnet for backpackers and nature lovers.

As well as being wealthier and more politically stable than its neighbours - the military was constitutionally abolished in 1949 - Costa Rica packs an amazing variety of natural beauty into an area little bigger than Switzerland, around one-quarter of which is national parkland.

The country's tourist trade is heavily geared towards outdoors pursuits, whether jungle trekking and bird watching or more vigourous activities such as surfing and white-water rafting.

But every year, one intrepid group - this time including me - goes a step further. They get to see the entire breadth of the country from the saddle of a bicycle.

La Ruta de los Conquistadores (The Route of the Conquerors) has, over the past 14 years, grown from an informal ride organised by an intrepid group of friends into one of Costa Rica's most famous events.

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