San Juan to Fort Lauderdale

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. The colonial-era fortifications have been awarded UNESCO World Heritage status, crowned by the imposing waterfront El Morro fortress, and the Old Town is full of attractive, brightly coloured houses. Outside of the Old Town you can find designer shopping on Avenida Ashford, and the north of the city is fringed by beautiful beaches, including fashionable Condado with its hip hotels and bars.

Marigot 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.

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.

Punta Cana is the broad swathe of coastline where the majority of the Dominican Republic’s resorts are clustered. The beaches are stunning, if rather overdeveloped in places, while inland attractions include the beautiful Ojos Indígenas ecological reserve.

Montego Bay is Jamaica’s tourism capital, and is the second largest city on the island after Kingston. The beach bars along the ‘Hip Strip’ offer a taste of the Jamaican way of life, with the ubiquitous Bob Marley providing the soundtrack; alternatively you may prefer an excursion to nearby sights such as Dunn’s River Falls or Seven Mile Beach.

Far more than just an offshore tax haven, Grand Cayman boasts the staggeringly beautiful white sands of Seven Mile Beach and some fantastic snorkelling in crystal clear waters. The capital, George Town, is a compact and friendly place, home to some interesting architecture and a suspiciously large number of registered companies.

Cozumel first made its name as an off the beaten track destination for divers, thanks to the crystalline waters and low key beach vibe. These days the cat is very much out of the bag, but get away from the craft shops and jewellery stores of the busy port and you’ll find a welcoming island community that is still authentically Mexican.

These days Fort Lauderdale is a sophisticated place awash with upmarket hotels and excellent restaurants. The glorious weather and swathes of golden beach are still a huge draw, but there are also plenty of cultural attractions, such as the Museum of Art and the Museum of Discovery and Science.