14-Day Yachtsman's Caribbean in Depth Cruise

Day 1 - San Juan

Arrive: Sat 05 December 2026 / Depart: Sat 05 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 2 - Frenchman's Cay, British Virgin Islands

Arrive: Sun 06 December 2026 / Depart: Sun 06 December 2026

Day 3 - St. Kitts

Arrive: Mon 07 December 2026 / Depart: Mon 07 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 4 - At Sea

Day 5 - Trois Ilets, Martinique

Arrive: Wed 09 December 2026 / Depart: Wed 09 December 2026

Les Trois-Îlets is a town on the Caribbean island of Martinique. It's known as the birthplace of Joséphine, Napoléon Bonaparte’s first wife. Her family’s sugar plantation is now the Pagerie Museum, with childhood mementos and a love letter from Napoléon. Nearby, exhibits at the Maison de la Canne detail how sugar cane shaped Martinique’s history. North, Pointe du Bout is a water-sports hub with boutiques and cafes.

Day 6 - Port Elizabeth (Grenadines)

Arrive: Thu 10 December 2026 / Depart: Thu 10 December 2026

Bequia’s Admiralty Bay is a favorite yachtsman’s anchorage. They ferry ashore to join the friendly, low-key locals “under the almond tree,” the chosen meeting place. Stroll along the Belmont Walkway to the Gingerbread for homemade nutmeg ice cream, or Frangipani, run by the daughter of a former prime minister. Continue to lovely, golden Princess Margaret Beach, or round the bend to Lower Bay. Don’t miss the excellent craftsmanship at the Sargeant Brothers Model Boat Shop, it’s a Bequia specialty.

Day 7 - Grenadine Islands

Arrive: Fri 11 December 2026 / Depart: Fri 11 December 2026

Day 8 - Barbados

Arrive: Sat 12 December 2026 / Depart: Sat 12 December 2026

Barbados is an eastern Caribbean island and an independent British Commonwealth nation. Bridgetown, the capital, is a cruise-ship port with colonial buildings and Nidhe Israel, a synagogue founded in 1654. Around the island are beaches, botanical gardens, the Harrison’s Cave formation, and 17th-century plantation houses like St. Nicholas Abbey. Local traditions include afternoon tea and cricket, the national sport.

Day 9 - At Sea

Day 10 - St. Kitts

Arrive: Mon 14 December 2026 / Depart: Mon 14 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 11 - Saint Pierre and Miquelon, Newfoundland, Canada

Arrive: Tue 15 December 2026 / Depart: Tue 15 December 2026

Saint Pierre and Miquelon is a French archipelago south of the Canadian island of Newfoundland. Sparsely populated Miquelon-­Langlade island contains the Grand Barachois lagoon, home to seabirds and seals. The busier Saint Pierre island has a distinct French atmosphere, with a cathedral and the Musée Heritage, which celebrates regional history. An island nearby, Île-aux-Marins, features an abandoned fishing village.

Day 12 - Terre de Haut, Ile des Saintes

Arrive: Wed 16 December 2026 / Depart: Wed 16 December 2026

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 13 - Roseau

Arrive: Thu 17 December 2026 / Depart: Thu 17 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 14 - Rodney Bay

Arrive: Fri 18 December 2026 / Depart: Fri 18 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 15 - Barbados

Arrive: Sat 19 December 2026 / Depart: Sat 19 December 2026

Barbados is an eastern Caribbean island and an independent British Commonwealth nation. Bridgetown, the capital, is a cruise-ship port with colonial buildings and Nidhe Israel, a synagogue founded in 1654. Around the island are beaches, botanical gardens, the Harrison’s Cave formation, and 17th-century plantation houses like St. Nicholas Abbey. Local traditions include afternoon tea and cricket, the national sport.