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.

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 island of Dominica stands out from the rest of the Caribbean, a rugged natural paradise that remains blissfully free of mass market tourism. The capital, Roseau, is pleasant enough, but the island interior offers so much more, including thick jungle, bubbling hot springs, cascading waterfalls and abundant birdlife.

Santo Domingo is the oldest continuously inhabited European settlement in the Americas, founded in 1496 by Bartholomew Columbus (Christopher’s brother). The city’s history is most keenly felt amongst the streets of the Zona Colonial, home to beautiful old churches and colonial era houses.

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.

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.

Belize’s capital does not enjoy the best reputation, and we wouldn’t recommend spending too much time here; use it instead as a jumping-off point to explore the fascinating Mayan ruins of Xunantunich, Lamanai and Altun Ha, or take a snorkelling trip to the beautiful Barrier Reef, including the famous Blue Hole.

The port of Santo Tomás de Castilla sits on Guatemala’s sliver of Caribbean coastline, and serves as a jumping-off point to explore this fascinating country. Nearby highlights include the Mayan site of Quiriguá and colourful, laid-back Livingston, and it’s also possible to take a day trip by air to the famous ruins at Tikal.

Roatán is the largest and busiest of the Bay Islands, which sit off the coast of Honduras in the crystal clear waters of the Caribbean Sea. It’s a fantastic destination for divers and snorkellers, with a stunning reef just offshore, and also boasts some lovely beaches.

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.