Leeward Island Holiday Cruise

Day 1 - Miami

Arrive: Sun 20 December 2026 / Depart: Sun 20 December 2026

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 - San Juan

Arrive: Wed 23 December 2026 / Depart: Wed 23 December 2026

Puerto Rico has been voluntarily associated with the United States since it was ceded by Spain in 1898. In 1952, this island country became a self-governing commonwealth territory of the United States. The capital, San Juan, is a teeming city of over 1.5 million. Remnants of colonial architecture stand side by side with the most modern high rises in this city of contrasts. The 7-square-block area, which contains the historic zone of Old San Juan, was once completely encircled by city walls and is still guarded by the impressive forts of El Morro and San Cristobal, which loom over the harbor as reminders of the centuries of Spanish rule. El Yunque rainforest, on the northeastern side of the island, is just one of many distinctive geographical features found here. Mountain lakes, waterfalls, teak forests, and three magnificent phosphorescent bays offer the visitor a variety of diversions.

Day 5 - Road Bay

Arrive: Thu 24 December 2026 / Depart: Thu 24 December 2026

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 6 - St. Kitts

Arrive: Fri 25 December 2026 / Depart: Fri 25 December 2026

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 - Marigot, Saint Martin

Arrive: Sat 26 December 2026 / Depart: Sat 26 December 2026

Tucked beside a lovely cove on the French side of this Dutch/French island, Marigot’s streets are lined with boutiques and shops displaying the filigree ironwork and striped awnings of a Riviera village. In the shops, imported Gallic goods tempt you to sample everything from cheeses and cornichons to the latest fashions. Across the island, Dutch Philipsburg is a famous duty-free bazaar, and offers activities including a sailing race aboard real 12-meter America’s Cup yachts.

Day 8 - Terre de Haut, Ile des Saintes

Arrive: Sun 27 December 2026 at 08:00 / Depart: Sun 27 December 2026 at 17:00

The Iles des Saintes, a tiny cluster of islets off the southern coast of Guadeloupe is what the doctor ordered, if he ordered an unspoiled Caribbean experience. No franchise duty free, no big hotels, no casinos. It is what much of the Caribbean used to be like. Stroll around the little town of Bourg de Saintes. Shop for real French cosmetics from the sidewalk vendors. Grab a seat and a beer and revel in the weather and the pace of the past.

Day 9 - Fort de France

Arrive: Mon 28 December 2026 at 08:00 / Depart: Mon 28 December 2026 at 18:00

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 10 - Rodney Bay

Arrive: Tue 29 December 2026 / Depart: Tue 29 December 2026

This is the island’s yachting center, quieter and less crowded than the main port of Castries. You can visit the island’s “drive-in” volcano at Soufriere, view the iconic peaks of the Pitons or perhaps snorkel at Pigeon Island, one of Jacques Cousteau’s favorite dive spots.

Day 11 - Roseau

Arrive: Wed 30 December 2026 / Depart: Wed 30 December 2026

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 12 - Little Bay, Montserrat

Arrive: Thu 31 December 2026 at 08:00 / Depart: Thu 31 December 2026 at 18:00

Day 13 - St John's, Antigua

Arrive: Fri 01 January 2027 at 08:00 / Depart: Fri 01 January 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 14 - Jost Van Dyke

Arrive: Sat 02 January 2027 / Depart: Sat 02 January 2027

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 15 - At Sea

Day 16 - At Sea

Day 17 - Miami

Arrive: Tue 05 January 2027 / Depart: Tue 05 January 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.