14-Day Yachtsman's Caribbean in Depth

Marigot Bay is St. Martin's French-side anchorage, where café culture, Fort Louis panoramas, and the nearby 'Gourmet Capital' village of Grand Case create the Caribbean's most elegant expression of Franco-Caribbean civilization. Visit December through April via Seabourn or Windstar for waterfront market spices, lobster thermidor, and the island that proves two nations sharing one coastline produces complementarity rather than conflict.

Frenchman's Cay is a tranquil island connected to Tortola's West End in the British Virgin Islands, home to the charming Soper's Hole Marina, excellent Caribbean-French dining, and access to top-rated wreck diving at the RMS Rhone. Must-dos include dining waterfront overlooking the Sir Francis Drake Channel, snorkeling the western reef systems, and diving the historic Rhone shipwreck. Visit December through April for dry, trade-wind-cooled weather and the calmest seas.

Friars Beach is St. Kitts' secluded southeastern escape, where golden sand, glassy turquoise water, and the volcanic silhouette of Nevis create a Caribbean beach experience mercifully free of resort development. Visit December through April as a Seabourn exclusive for beach barbecues, reef snorkeling, and the reminder that the Caribbean's greatest luxury remains the simplest — perfect sand meeting warm, impossibly blue water.

Trois-Îlets is Empress Joséphine's Martinican birthplace, where the Musée de la Pagerie presents her extraordinary life alongside the Savane des Esclaves slave settlement reconstruction — French Caribbean beauty and historical complexity presented without diminishment. Visit December through May via Seabourn for sheltered bay beaches, artisan village pottery, and the most historically nuanced Martinique experience available.

Port Elizabeth is the beguiling waterfront capital of Bequia, a former whaling island in Saint Vincent and the Grenadines where Caribbean authenticity endures in gingerbread cottages, hand-built schooners, and charcoal-grilled lobster on the sand. Stroll the Belmont Walkway for the island's finest harbour views, then sail to the Tobago Cays for world-class snorkelling among sea turtles. The dry season from December through May offers the most reliable sunshine and the peak of luxury cruise calls into sheltered Admiralty Bay.

St. George's, Grenada, is a vibrant port known for its rich history, stunning architecture, and fragrant markets brimming with local spices. Must-do experiences include savoring the local delicacies at the Market Square and exploring nearby Carriacou Island for its tranquil beaches. The best season to visit is from December to April, when the weather is pleasantly warm and dry.

Bridgetown, Barbados's compact and convivial capital, carries three centuries of uninterrupted British colonial heritage — a UNESCO World Heritage Site of Georgian townhouses, coral-stone churches, and the Garrison Savannah, whose racecourse is the oldest in the Western Hemisphere — all infused with the irresistible rhythms of a proud Caribbean nation. The island's culinary scene has matured into one of the Caribbean's most sophisticated, with flying fish cutter sandwiches from roadside stalls competing for devotion with the elegant seafood preparations of the Platinum Coast's celebrated restaurants. Visit December through May for the driest season; the island's sheltered west coast offers superlative year-round sailing conditions.

Friars Beach is St. Kitts' secluded southeastern escape, where golden sand, glassy turquoise water, and the volcanic silhouette of Nevis create a Caribbean beach experience mercifully free of resort development. Visit December through April as a Seabourn exclusive for beach barbecues, reef snorkeling, and the reminder that the Caribbean's greatest luxury remains the simplest — perfect sand meeting warm, impossibly blue water.

Terre-de-Haut is the enchanting main island of Les Saintes off Guadeloupe, settled by Breton fishermen and graced with one of the Caribbean's most beautiful bays, a Napoleonic fort, and exceptional seafood. Must-dos include snorkeling at Pain de Sucre beach, hiking to the Chameau summit for panoramic views, and tasting the legendary tourment d'amour coconut tart. Visit December through May for dry, sunny weather and comfortable trade-wind breezes.

Saint-Pierre, Martinique, was the "Paris of the Caribbean" until Mount Pelée's catastrophic 1902 eruption destroyed the city in seconds, killing nearly 30,000 people. Must-do experiences include visiting the Volcanological Museum with its haunting artifacts, exploring the atmospheric ruins, and diving the coral-encrusted shipwrecks in the harbor. December through May offers the driest weather for exploring this compelling intersection of natural disaster history and Caribbean beauty.

Roseau, the capital of Dominica, is a vibrant port city characterized by its colonial architecture and rich cultural heritage. Must-do experiences include savoring local delicacies like mountain chicken curry and visiting the bustling Roseau Market. The best time to visit is during the dry season from December to April, when the island showcases its natural beauty and festive spirit.

Rodney Bay is Saint Lucia's premier resort and marina district on the island's northwest coast, combining golden Reduit Beach, a vibrant dining scene at the yacht marina, and easy access to the island's volcanic interior. Must-dos include swimming at Reduit Beach, tasting Creole lambi at the marina restaurants, and excursions to the Pitons and the Sulphur Springs drive-in volcano. Visit January through April for the driest weather and calmest Caribbean seas.

Bridgetown, Barbados's compact and convivial capital, carries three centuries of uninterrupted British colonial heritage — a UNESCO World Heritage Site of Georgian townhouses, coral-stone churches, and the Garrison Savannah, whose racecourse is the oldest in the Western Hemisphere — all infused with the irresistible rhythms of a proud Caribbean nation. The island's culinary scene has matured into one of the Caribbean's most sophisticated, with flying fish cutter sandwiches from roadside stalls competing for devotion with the elegant seafood preparations of the Platinum Coast's celebrated restaurants. Visit December through May for the driest season; the island's sheltered west coast offers superlative year-round sailing conditions.