14-Day Southern Caribbean: Abc & Windward Islands Holiday

Fort Lauderdale is South Florida's reinvented waterfront city, where three hundred miles of inland waterways, the NSU Art Museum's contemporary collection, and the tree-lined Las Olas Boulevard create a cruise departure point of genuine sophistication at Port Everglades. Arrive a day early between November and April to explore the 'Venice of America' by water taxi and discover the dining scene that has replaced Spring Break with year-round culinary ambition.

Key West is the southernmost point of the continental United States, a tropical island of Victorian conch houses, Hemingway's six-toed cats, and the only living coral reef in the country. Must-dos include touring the Hemingway Home, tasting authentic Key lime pie and conch fritters, and watching the sunset spectacle at Mallory Square. November through April offers the most comfortable weather with lower humidity and warm ocean temperatures.

Oranjestad shimmers with an unlikely elegance — Dutch colonial architecture painted in ochre, terracotta, and sky-blue lining streets just fifteen miles off the Venezuelan coast, in a perpetual trade wind that keeps the island blissfully dry and golden-skied almost every day of the year. The island's Arikok National Park preserves ancient Caquetío petroglyphs, a rugged volcanic interior, and the dramatic Natural Pool carved from black rock on the windward coast. Eagle Beach, consistently ranked among the finest beaches in the Caribbean, lies minutes from the capital. Aruba's reliably brilliant weather — average 29°C with near-zero hurricane risk — makes it genuinely year-round, though December through April is the classic season.

Charlotteville is a tranquil fishing village at Tobago's northeastern tip, nestled beside Man-O-War Bay and the world's oldest protected rainforest, the Main Ridge Forest Reserve. Must-dos include snorkeling at Pirates Cove, tasting curried crab and dumplings, and hiking through the primary rainforest to spot hummingbirds and motmots. The dry season from January to May offers the calmest seas and most comfortable weather.

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.

Castries, the capital of St. Lucia, is a vibrant port steeped in history and culture, offering stunning architecture and a lively market atmosphere. Must-do experiences include savoring the national dish, green fig and saltfish, and exploring the picturesque Marigot Bay. The best time to visit is during the dry season from December to April, when the weather is perfect for exploring this Caribbean gem.

San Juan near Peru's Paracas Peninsula sits where the arid Atacama coast meets the Humboldt Current's rich marine ecosystem, offering the wildlife-packed Ballestas Islands, the mysterious Candelabra geoglyph, and world-class ceviche from the freshest seafood. Visitors should boat to the Ballestas to see Humboldt penguins and sea lions, taste Pisco Sour at its source, and explore pre-Columbian Paracas textile heritage. The dry climate is pleasant year-round, with June through September ideal for boat excursions.

Half Moon Cay, a private island paradise in the Bahamas, is renowned for its stunning beaches and serene atmosphere. Must-do experiences include savoring local delicacies like conch fritters and exploring the vibrant markets. The best time to visit is during the winter months when the weather is pleasantly warm and inviting.

Fort Lauderdale is South Florida's reinvented waterfront city, where three hundred miles of inland waterways, the NSU Art Museum's contemporary collection, and the tree-lined Las Olas Boulevard create a cruise departure point of genuine sophistication at Port Everglades. Arrive a day early between November and April to explore the 'Venice of America' by water taxi and discover the dining scene that has replaced Spring Break with year-round culinary ambition.