14 January

Sint Maarten: Philipsburg

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.

15 January

Guadeloupe: Terre-de-Haut

Eight tiny islands make up the Iles des Saintes, a sparsely inhabited archipelago off the southern coast of Guadeloupe. The most interesting island is hilly Terre-de-Haut, almost entirely populated by the fair-skinned descendants of Breton sailors and home to a beautiful bay reminiscent of a mini Rio de Janeiro.

16 January

Bermuda: St George's

St George’s was the first permanent British settlement in Bermuda and the first capital, situated at the eastern end of the islands. The town's charming historic architecture has earned it UNESCO World Heritage Site status, and there are several interesting museums, forts and churches.

17 January

Saint Lucia: Castries

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.

18 January - At sea

19 January

Dominican Republic: Puerto Plata

20 January - At sea

21 January

United States: Miami

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.

22 January to 23 January - At sea

24 January

U.S. Virgin Islands: Charlotte Amalie (St Thomas)

The busiest and most developed of the Virgin Islands, St. Thomas is nevertheless blessed with typically Caribbean good looks. The main town, Charlotte Amalie, is situated on a perfect natural harbour, and in its colonial heyday its warehouses were filled with indigo, tobacco and cotton.

25 January

Anguilla: Road Bay

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.

26 January

Martinique: Saint Pierre (Martinique)

27 January

Saint Kitts and Nevis: Basseterre (Saint Kitts)

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.

28 January

Sint Maarten: Philipsburg

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.

29 January

Arriving in 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.