26 October to 27 October - At sea

28 October

U.S. Virgin Islands: Cruz Bay (St John)

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.

29 October

Antigua and Barbuda: St John's

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.

30 October

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.

31 October

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.

1 November

Puerto Rico: 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.

2 November

British Virgin Islands: Tortola

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.

3 November

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.

4 November to 5 November

Saint Barthélemy: Gustavia

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.

5 November

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.

6 November to 7 November - At sea

8 November

Arriving in 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.