14-Day Windward & Leeward Islands Cruise

Day 1 - Miami

Arrive: Sat 04 December 2027 / Depart: Sat 04 December 2027 at 16:00

Miami is the busiest cruise port in the world, hosting a myriad of ships year-round from all over the globe. Although it is technically not on the Caribbean Sea, no other American city exudes more of the diverse tropical appeal of the Caribbean. The city is home to a large and vibrant immigrant population that blends snowbird refugees from more northern climes with emigres from all Latin America and the Caribbean, as well as sizable groups from Europe, the Middle East and Asia. From the hot-blooded Art Deco haunts of South Beach to the natural wonders of the UNESCO-inscribed Everglades and the laid-back charms of the Keys, South Florida offers a bounty of appealing attractions that make an extended stay in the region nearly mandatory for those either embarking or disembarking here.

Day 2 - At Sea

Day 3 - At Sea

Day 4 - St John's, Antigua

Arrive: Tue 07 December 2027 at 10:00 / Depart: Tue 07 December 2027 at 18:00

Antigua is blessed with an abundance of shining white beaches, and many of these have sprouted top-end resort hotels that engender golf courses and other amenities counted among the best in the Caribbean. A pleasant drive up through farms and tiny villages leads to the commanding fortress on Shirley Heights, from which you can survey the town and the harbor of Nelson’s Dockyard across the island. Once a carenage for British frigates, today it is an enclave of shops and restaurants.

Day 5 - Gustavia, Saint Barthelemy

Arrive: Wed 08 December 2027 at 08:00 / Depart: Wed 08 December 2027 at 17:00

Tiny St. Barts, as it is commonly called, lies 125 miles northwest of the French island of Guadeloupe, of which it is a dependency. Its geographic features include steep, green, once-active volcano hills, deep valleys, and beautiful beaches. Founded by the French, ceded to Sweden then returned to France, the toy-scaled capital of Gustavia is built around the harbor on the island's southwest coast. Many of the island's inhabitants are descendants of settlers from Brittany, Normandy and Sweden. Today they operate small inns, cafes, restaurants and boutiques that are housed in old buildings of Swedish colonial and French Creole architecture. Too small for most cruise ships, Gustavia's harbor is a favorite layover for sailing yachts, and with prices well beyond the means of the masses, visits are mostly limited to a few hours of day-trippers from nearby St. Martin/St. Maarten. The majority of visitors staying on the island still come from among the privileged who treasure the laid-back atmosphere and small-gem perfection of St. Barts.

Day 6 - St. Kitts

Arrive: Thu 09 December 2027 at 08:00 / Depart: Thu 09 December 2027 at 17:00

A classic golden arc of sugary sand at South Friar’s Bay, Carambola is home to the island’s most luxurious beach clubs and restaurants. Umbrellas, loungers and optional water sports abound for those so inclined. Otherwise St. Kitts has other attractions, including a number of lovingly preserved plantation great houses, the UNESCO World Heritage Site of Brimstone Hill Fortress and a scenic narrow gauge sugarcane railway.

Day 7 - Fort de France

Arrive: Fri 10 December 2027 at 08:00 / Depart: Fri 10 December 2027 at 22:00

Fort-de-France, Martinique's capital, with its narrow streets and iron grill-worked balconies, brings to mind New Orleans or Nice. This distinctly French island is a full-fledged department of France, with members in parliament and the senate. Naturally, everyone speaks French, as well as a rapid-fire Creole. The island features a varied landscape, from quiet beaches to lush rain forest to imposing Mont Pelee. Not surprisingly, the shopping in Fort-de-France has a decidedly Gallic flair. Bienvenue to this bit of France in the Caribbean.

Day 8 - Roseau

Arrive: Sat 11 December 2027 at 08:00 / Depart: Sat 11 December 2027 at 17:00

The Caribbean’s verdant “Nature Island” has resolved not to succumb to the high-rise hotels and casino culture that predominate on some other islands. The tiny nation is determined to thrive on its natural resources, which are many and attractive. Water is one, and the island does export delicious mineral water throughout the area. There are also thermal springs and a “boiling lake,” as well as lovely waterfalls. Citrus fruits such as grapefruit are another export. The island is the source of Rose’s Lime Juice, a requisite of the perfect gimlet cocktail. Fragrant bay rum, distilled from native trees, is a handmade commodity much prized on the global market. Visit the peaceful Botanical Gardens, or ascend Morne Bruce for a stunning view over the town, the harbor and the sea beyond.

Day 9 - Little Bay, Montserrat

Arrive: Sun 12 December 2027 at 08:00 / Depart: Sun 12 December 2027 at 18:00

Day 10 - St John's, Antigua

Arrive: Mon 13 December 2027 at 08:00 / Depart: Mon 13 December 2027 at 17:00

Antigua is blessed with an abundance of shining white beaches, and many of these have sprouted top-end resort hotels that engender golf courses and other amenities counted among the best in the Caribbean. A pleasant drive up through farms and tiny villages leads to the commanding fortress on Shirley Heights, from which you can survey the town and the harbor of Nelson’s Dockyard across the island. Once a carenage for British frigates, today it is an enclave of shops and restaurants.

Day 11 - Road Bay

Arrive: Tue 14 December 2027 at 08:00 / Depart: Tue 14 December 2027 at 17:00

Anguilla’s name is based on the word for eel in several Romance languages, and its 17-mile length and three-mile width are appropriate to the analogy. The northernmost of the Leeward Islands chain, it is a British overseas territory. With its resources largely limited to an abundance of breathtaking beaches and coral reefs, the island’s main industries are tourism and the lucrative cultivation of offshore banking and insurance tax havens. Road Bay and its village of Sandy Ground comprise the main harbor for ships on the island, although the entire coastline is scalloped with lovely coves and anchorages that make it a magnet for yachtsmen. The official currency is the Eastern Caribbean dollar, although U.S. dollars are widely accepted. They might be well-spent on a luncheon of impeccably fresh seafood from the surrounding seas. There are no less than seven shipwrecks strewn along the island’s barrier reefs, which have made it the wreck-diving capital of the region.

Day 12 - Jost Van Dyke

Arrive: Wed 15 December 2027 at 07:00 / Depart: Wed 15 December 2027 at 14:00

There are approximately 40 British Virgin Islands (the exact number varies from authority to authority), many of which are uninhabited. Some have only a handful of residents. Jost Van Dyke has a small population of its own families: the Turners, Grants, Ringes and Callwoods to name the majority. The desire to continue in the old ways is strong here, and "Jost" looks much as it must have looked 100 or 200 years ago. This archipelago is pristine and traffic light free. Weather permitting, your captain will anchor in this idyllic location and deploy the Marina for a day of play in the sea and sun.

Day 13 - At Sea

Day 14 - At Sea

Day 15 - Miami

Arrive: Sat 18 December 2027 at 07:00 / Depart: Sat 18 December 2027

Miami is the busiest cruise port in the world, hosting a myriad of ships year-round from all over the globe. Although it is technically not on the Caribbean Sea, no other American city exudes more of the diverse tropical appeal of the Caribbean. The city is home to a large and vibrant immigrant population that blends snowbird refugees from more northern climes with emigres from all Latin America and the Caribbean, as well as sizable groups from Europe, the Middle East and Asia. From the hot-blooded Art Deco haunts of South Beach to the natural wonders of the UNESCO-inscribed Everglades and the laid-back charms of the Keys, South Florida offers a bounty of appealing attractions that make an extended stay in the region nearly mandatory for those either embarking or disembarking here.