14-Day Windward & Leeward Islands

Miami is a pulsating modern city, a cultural crossroads where Cuban émigrés rub shoulders with affluent New Yorkers topping up on winter sun, and where you're just as likely to hear Spanish or Caribbean patois being spoken as you are English. Downtown Miami is a destination in its own right, with a host of world class galleries including the fantastic MOCA (Museum of Contemporary Art), 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.

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.

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.

The beach at South Friars Bay is a lovely sweep of golden sand at the southern end of St Kitts, although it can get a little busy when the larger cruise ships are docked on the island. There are several bars and restaurants along this half-mile stretch, with watersports equipment and loungers available to rent.

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.

The island of Dominica stands out from the rest of the Caribbean, a rugged natural paradise that remains blissfully free of mass market tourism. The capital, Roseau, is pleasant enough, but the island interior offers so much more, including thick jungle, bubbling hot springs, cascading waterfalls and abundant birdlife.

Montserrat garnered global attention in 1995 when the Soufrière Hills volcano erupted, burying the island’s capital, Plymouth. Although an exclusion zone is still in place in the south, visitors are often surprised by how lush and unspoilt the rest of the island is, home to a colourful variety of birdlife.

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.

Tiny Anguilla is home to no less than 33 beaches, blessed with some of the most gloriously white sands in the Caribbean. A clutch of high end hotels and gourmet restaurants attract a well-to-do crowd, but the island has a more low key, laid back vibe than its glitzy neighbours, St Martin and St Barths.

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.

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.