14-Day Southern Caribbean in Depth

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.

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.

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.

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.

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.

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.

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.

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.

Barbados has retained many of the trappings of its British colonial heritage. Judges and barristers wear proper robes and wigs, police don helmets styled after London bobbies and cricket remains a national passion. Barbados also has all the sporting appeal of the rest of the Caribbean, with pristine beaches, powerful surf and crystal clear waters. Brightly colored homes and hibiscus flowers mingle with mahogany trees and English churches dating back to the 17th century.