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.