San Juan to San Juan

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.

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.

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.

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 volcanic French Caribbean island of Martinique is a land of contrasts, from the lush rainforests of the north to the busy streets of the capital, Fort-de-France. There are plenty of lovely beaches geared towards relaxation, and the French influence also means that the cuisine is a cut above the usual Caribbean fare.

Browse the markets of charming St George’s, fragrant with the scent of cinnamon and nutmeg, and you’ll soon understand why Grenada is known as the ‘isle of spice’. This is one of the Caribbean’s most enchanting islands, fringed by gorgeous beaches and largely unsullied by mass market tourism.

The quiet, cactus-covered Dutch Caribbean island of Bonaire is internationally renowned for its diving, ringed by spectacular coral reefs that teem with life. The capital, Kralendijk, is home to some pretty colonial architecture, and the island is also known for its flamingos and pink sand beaches.

The gabled houses of Willemstad lend an undeniably Dutch feel to the capital of little Curaçao, with a splash of Caribbean colour thrown in. The island itself is not your typical lush tropical paradise - the landscape is characterised instead by thorny shrubs and cacti - but there are some fantastic beaches and quaint little villages.

The tiny Dutch Caribbean island of Aruba, located just off the coast of Venezuela, lies outside of the hurricane belt, meaning it enjoys a largely dry climate, and boasts some of the best beaches in the region, if not the world.

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.