Barbados and Southern Caribbean from Bridgetown

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.

Fort-de-France, Martinique's gracious capital, blends French metropolitan sophistication with deep Caribbean soul in a way that no other island quite replicates. The Bibliothèque Schoelcher, a beautiful Art Nouveau building transported piece by piece from Paris for the 1889 World's Fair, anchors a downtown of wrought-iron balconies and aromatic spice markets. The surrounding countryside offers rum distilleries — some of the finest aged agricole rums in the world — dramatic rainforest hikes, and the haunting ruins of Saint-Pierre, destroyed by Mont Pelée's catastrophic 1902 eruption. December through May brings the driest, sunniest weather on this endlessly captivating island.

Pointe-à-Pitre is the bustling capital of Guadeloupe, offering a vibrant mix of Creole culture, historical significance, and stunning natural beauty. Must-do experiences include sampling the local delicacies like “colombo de poulet” and exploring the nearby Îles des Saintes for their breathtaking beaches. The best season to visit is from mid-December to mid-April, when the weather is pleasantly warm and dry.

Road Town, the capital of the British Virgin Islands, is a vibrant port known for its colonial charm and rich history. Must-do experiences include savoring local delicacies like fungi and callaloo, and exploring the stunning Baths on Virgin Gorda. The best season to visit is during the dry winter months, from December to April, when the weather is most pleasant for outdoor adventures.

La Romana is a vibrant port in the Dominican Republic, known for its stunning beaches and rich cultural heritage. Must-do experiences include savoring La Bandera, the local culinary staple, and exploring nearby attractions like Catalina Island and Cayo Levantado. The best season to visit is from December to April, when the weather is pleasantly warm and dry.

Catalina Island, or La Isla Catalina, is a captivating port in the Dominican Republic known for its historical charm and stunning landscapes. Must-do experiences include savoring local dishes such as "pescado frito" and exploring nearby attractions like Amber Cove and Cayo Levantado. The best time to visit is during the winter months, when the weather is delightful and the island is bustling with activity.

Virgin Gorda is a stunning port in the British Virgin Islands known for its dramatic landscapes and rich history. Must-do experiences include exploring The Baths' unique rock formations and savoring local dishes like Roti and Fish Escovitch. The best season to visit is from December to April, when the weather is optimal for outdoor adventures.

Philipsburg, capital of the Dutch side of Sint Maarten, packs extraordinary energy onto a narrow sand spit between Great Bay and the Great Salt Pond — two parallel streets of duty-free boutiques, creole restaurants, and rum bars backed by a beach where cruise ships anchor so close that their hulls seem to dominate the shoreline. The island's most celebrated spectacle is entirely involuntary: Princess Juliana International Airport, where landing aircraft pass at rooftop height over Maho Beach, drawing crowds of thrill-seekers every day. The 1648 Mount Concordia Treaty, dividing this sliver of land between France and the Netherlands, created the world's smallest territory shared by two nations. The dry season from December to April is optimal.

Fort-de-France, Martinique's gracious capital, blends French metropolitan sophistication with deep Caribbean soul in a way that no other island quite replicates. The Bibliothèque Schoelcher, a beautiful Art Nouveau building transported piece by piece from Paris for the 1889 World's Fair, anchors a downtown of wrought-iron balconies and aromatic spice markets. The surrounding countryside offers rum distilleries — some of the finest aged agricole rums in the world — dramatic rainforest hikes, and the haunting ruins of Saint-Pierre, destroyed by Mont Pelée's catastrophic 1902 eruption. December through May brings the driest, sunniest weather on this endlessly captivating island.

St. John's, Antigua's storied capital, anchors a natural harbor that has drawn seafarers since the seventeenth century, its Georgian cathedral and pastel-painted market hall bearing quiet witness to a complex colonial past. The crown jewel lies an hour's drive away at Nelson's Dockyard in English Harbour — the world's only still-functioning Georgian naval dockyard, set against the turquoise waters of one of the Caribbean's finest anchorages. Antigua's warm, dry climate makes it a year-round destination, though the exhilarating Sailing Week regatta in late April draws the most glamorous international crowd.

La Romana is a vibrant port in the Dominican Republic, known for its stunning beaches and rich cultural heritage. Must-do experiences include savoring La Bandera, the local culinary staple, and exploring nearby attractions like Catalina Island and Cayo Levantado. The best season to visit is from December to April, when the weather is pleasantly warm and dry.

Catalina Island, or La Isla Catalina, is a captivating port in the Dominican Republic known for its historical charm and stunning landscapes. Must-do experiences include savoring local dishes such as "pescado frito" and exploring nearby attractions like Amber Cove and Cayo Levantado. The best time to visit is during the winter months, when the weather is delightful and the island is bustling with activity.

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.