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.

Antigua is famously home to 365 beaches - one for every day of the year - and there is an undeniable allure to the many white sand coves dotted along the coast. The capital, St John's, is worth a look, but if you've got time to visit the south coast you'll find historic Nelson's Dockyard a lot more interesting.

Castries, Saint Lucia’s diminutive capital, is home to some interesting markets and colonial buildings. The island’s highlights are situated elsewhere, however, and we’d recommend either heading south towards Soufrière, where the iconic Piton mountains guard a beautiful bay, or north to the bars, restaurants and beaches of Rodney Bay.

There’s more to Barbados than just beaches; the delightful architecture of the old garrison in Bridgetown, the capital, is fully deserving of its UNESCO World Heritage status, and the island interior is littered with old sugar plantations and natural wonders such as Harrison’s Cave.

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.

Tortola is the largest and most populous of the British Virgin Islands, and the bustling port at Road Town is a magnet for sailors from around the world. The island is blessed with some gorgeous beaches and secluded coves, and it’s a great place for a spot of snorkelling.

Downtown Miami is a destination in its own right, with a host of world class galleries, 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.

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.

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.

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.

The port at Costa Maya is a purpose-built facility for cruise passengers, with amenities including swimming pools, restaurants and bars. The neighbouring village of Mahahual will give you a slightly more authentic taste of the Yucatán, and the ruined Mayan city of Chacchoben is an hour’s drive away.

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.