Miami to San Juan

Miami is a pulsating modern city, a cultural crossroads where Cuban émigrés rub shoulders with affluent New Yorkers topping up on winter sun, and where you're just as likely to hear Spanish or Caribbean patois being spoken as you are English. Downtown Miami is a destination in its own right, with a host of world class galleries including the fantastic MOCA (Museum of Contemporary Art), but it's still Miami Beach that draws the biggest crowds. The Art Deco district around South Beach is very much back in vogue, with new restaurants, bars and luxury developments sprouting up all over the place.

St John is the quietest and least developed of the US Virgin Islands, with two thirds of the island designated as a National Park. There are several hiking trails that showcase the island’s unspoilt natural beauty, and it’s a popular spot for aquatic pursuits including snorkelling, kayaking and scuba diving.

Philipsburg is the gateway to an intriguing little Caribbean island with a dual personality: the Dutch side, St. Maarten, is the livelier of the two, with shopping malls, casinos and more of a nightlife scene, while French-speaking St. Martin is a more refined (and more expensive) affair, with a laid-back, continental air and a host of exclusive resorts and restaurants.

Laid back and low key, Saint Kitts is an island typified by rolling green hills, characterful beach bars and the lingering remnants of the sugar cane trade that once dominated here. Attractions include the UNESCO-listed Brimstone Hill fortress, the 18-mile Scenic Railway and the faded Georgian elegance of the capital, Basseterre.

Eight tiny islands make up the Iles des Saintes, a sparsely inhabited archipelago off the southern coast of Guadeloupe. The most interesting island is hilly Terre-de-Haut, almost entirely populated by the fair-skinned descendants of Breton sailors and home to a beautiful bay reminiscent of a mini Rio de Janeiro.

The volcanic French Caribbean island of Martinique is a land of contrasts, from the lush rainforests of the north to the busy streets of the capital, Fort-de-France. There are plenty of lovely beaches geared towards relaxation, and the French influence also means that the cuisine is a cut above the usual Caribbean fare.

Montserrat garnered global attention in 1995 when the Soufrière Hills volcano erupted, burying the island’s capital, Plymouth. Although an exclusion zone is still in place in the south, visitors are often surprised by how lush and unspoilt the rest of the island is, home to a colourful variety of birdlife.

The idyllic island of Jost Van Dyke, named after an early Dutch settler, is known for its laid back vibe and friendly beach bars, including the famous Foxy’s, which counts Keith Richards amongst its past customers. It’s a place to kick back and relax, and the clear blue waters are also perfect for snorkelling.

Founded by the Spanish in 1521, Puerto Rico’s capital is the second oldest European settlement in the Americas. Modern San Juan is a bustling city, home to over a third of the island’s population, but the cobbled streets of the Old Town remain the biggest tourist draw.