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.

Port Royal was once known as ‘the most wicked and sinful city in the world’, a den of vice that was home to pirates, slave traders and other undesirables. A huge earthquake in 1692 destroyed much of the city, with the ruins submerged under the sea. Port Royal is also close to Jamaica’s capital, Kingston, a must visit for fans of Bob Marley.

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.

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.

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.

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.

Gustavia is the chic and petite capital of Saint Barths, a tiny French Caribbean island that’s renowned as a haunt of the rich and the famous. You can certainly live well here if you’ve got the means, with an array of gourmet restaurants and luxury boutiques aimed squarely at the A-list. The beautiful beaches, on the other hand, are free and open to all.

Situated on Colombia’s Caribbean coast, Santa Marta is the oldest surviving Spanish colonial city in South America. The modern city lacks some of the charm of nearby Cartagena, but tourism has come on leaps and bounds in recent years, with a number of ambitious regeneration projects and a host of new restaurants and bars.

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.