An Extended Journey of Secluded Isles & Coastal Havens

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.

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.

Providenciales, known locally as ‘Provo’, is the most developed and most populated of the Turks and Caicos islands, home to high end luxury resorts and mile after mile of stunning white sand beach. The surrounding reefs offer spectacular snorkelling and scuba diving, with turtles, dolphins, rays and sharks lurking amongst the coral.

Colourful and eccentric, the island city of Key West stands apart from the rest of Florida. A strong Caribbean influence reflects the city’s proximity to Cuba and the Bahamas, and it has long been known as a bohemian hangout, a welcoming and open-minded place that Ernest Hemingway once called home.

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.

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.

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.

St John is the quietest and least developed of the US Virgin Islands, with two thirds of the island designated as a National Park. There are several hiking trails that showcase the island’s unspoilt natural beauty, and it’s a popular spot for aquatic pursuits including snorkelling, kayaking and scuba diving.

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.