Day 1 (DEC 2, 2025): San Juan, Puerto Rico

Departs @ 9:00pm.

Puerto Rico is the easternmost island in the Greater Antilles chain and an unincorporated territory of the United States. The “Island of Enchantment” dazzles with its vibrant culture, Old San Juan — a colonial charmer with leafy plazas and mix of Gothic, Renaissance and Baroque architecture — and the UNESCO World Heritage-designated La Fortaleza and fortresses of San Felipe del Morro and San Cristobál. Natural wonders include a slew of gorgeous beaches, lush reserves like Caja de Muertos and El Yunque — the only tropical rainforest in the U.S. — surreal bioluminescent bays, and Cueva Ventana, a cliff-side cave with Taino petroglyphs and much-photographed “window” overlooking the Arecibo River Valley.

Day 2 (DEC 3, 2025): Day at Sea

Day 3 (DEC 4, 2025): Oranjestad, Aruba

The countryside is dotted with cottages surrounded by cactus fences and bright splashes of bougainvillea, oleander and hibiscus. During our call, enjoy a stroll through the capital, Oranjestad. Colorful Wilhelminastraat is lined with typical Aruban buildings of the Dutch Colonial style, and plenty of shops offering duty-free goods.

Day 4 (DEC 5, 2025): Willemstad, Curacao

Delightful Willemstad is the capital of the five-island Netherlands Antilles, which in turn are part of the Kingdom of the Netherlands. Gabled buildings bring to mind Dutch cities, while working windmills dot the countryside, helping to provide the island with much-needed fresh water. Shoppers will find no shortage of temptations here, while those so inclined will find excellent snorkeling opportunities.

Day 5 (DEC 6, 2025): Kralendijk, Bonaire

Indian drawings, which can be seen today in several places, depict life and events which took place centuries before the island's discovery by Europeans. Today, the island's economy depends largely on tourism. A friendly 'bon bini' from the locals greets you during your visit ashore. Enjoy a stroll through Kralendijk, past the fish market, duty-free shops of Breedestraat, the waterfront promenade and the quaint toy-like houses exemplifying the Dutch colonial architecture.

Day 6 (DEC 7, 2025): Day at Sea

Day 7 (DEC 8, 2025): Trois Ilets, Martinique

Martinique is one of the most colorful and interesting islands in the Caribbean. Perhaps the most famous attraction in this area is the colonial plantation called La Pagerie, the birthplace and childhood home of Josephine Beauharnais, the Martinique-born woman who became the second wife and Empress to Napoleon Bonaparte. The stately plantation house and its manicured grounds are now a museum, furnished with period pieces and illustrating the privileged lifestyle of the master class during the French colonial slave period. Fort-de-France is a bustling seaport and market town, with handsome reminders of its colonial past including the ornate Schoelcher Library imported stone-by-stone from France. The graceful cathedral and lush botanical gardens of Balata provide some relief, in the form of luxuriant tropical flowers, butterflies and hummingbirds.

Day 8 (DEC 9, 2025): Roseau, Dominica

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 (DEC 10, 2025): Little Bay, Montserrat

Little Bay’s charm lies in its intimate and unspoiled nature, offering a picturesque escape that’s as peaceful as it is beautiful. The bay is framed by lush, verdant hills that provide a stunning backdrop, while the warm, crystal-clear waters beckon for a refreshing dip or a leisurely swim. Whether you’re seeking solace in the sun, indulging in a beachside picnic, or exploring the vibrant marine life with a snorkel, Little Bay offers a perfect blend of relaxation and natural wonder.

Day 10 (DEC 11, 2025): Carambola Beach, Saint Kitts and Nevis

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 11 (DEC 12, 2025): St. Johns, Antigua and Barbuda

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 12 (DEC 13, 2025): Tortola, British Virgin Islands

Tortola is the business and touristic center of the BVI. The island has all the elements of an ideal Caribbean playground: dozens of soft sand beaches, clear water and hidden coves, a wealth of touristic infrastructure from rental cars and scooters to motor launches and sailing yachts. Besides gorgeous beaches such as Smuggler’s Cove, Apple Bay and Cane Garden Bay, there are historical attractions on Tortola including the Lower Estate Sugar Works Museum, the Mount Healthy Windmill and Fort Burt. Many visitors also opt for attractions on nearby islands such as The Baths or the Bitter End Yacht Club on Virgin Gorda or famous laid-back bars like Foxy’s on Jost Van Dyke.

Day 13 (DEC 14, 2025): San Juan, Puerto Rico

Arrive @ 7:00 am