7-Day Exotic Caribbean Explorer

Miami is a city of perpetual reinvention — the Art Deco jewel of South Beach giving way to the street-art murals of Wynwood, the Cuban rhythms of Calle Ocho, and the glass-and-steel towers of a skyline that has redrawn itself every decade since Julia Tuttle convinced Henry Flagler to extend his railroad south in 1896. Must-dos include strolling the pastel-fronted Ocean Drive at dusk and exploring the world-class collections at the Pérez Art Museum Miami overlooking Biscayne Bay. November through April delivers idyllic weather — warm and dry — while summer brings heat, humidity, and hurricane risk. Miami handles cruise departures elegantly, with the Port of Miami a short taxi ride from the best neighbourhoods.

Guadeloupe is a butterfly-shaped French Caribbean archipelago where volcanic rainforests, pristine beaches, and refined Creole-French cuisine create one of the region's most distinctive destinations. Must-dos include hiking La Soufrière volcano, tasting rhum agricole, and day-tripping to the Saintes islands. December through May offers the driest, most comfortable conditions for visiting.

Basseterre, capital of Saint Kitts and Nevis — the smallest sovereign nation in the Americas — is the gateway to an island whose volcanic drama and layered colonial history distinguish it from every other Caribbean port. Mount Liamuiga's cloud-capped summit and its rainforest-filled crater lake await hikers, while the UNESCO-listed Brimstone Hill Fortress, one of the finest surviving examples of British colonial military architecture, commands sweeping views across neighboring islands. The surrounding plantation inns — sugar estates converted into intimate boutique hotels — offer the most atmospheric accommodation in the Eastern Caribbean. Visit November through April for the driest, sunniest weather.

San Juan, Puerto Rico's radiant colonial capital, is one of the Americas' most compellingly layered cities — a place where the sixteenth-century fortresses of El Morro and San Cristóbal stand sentinel over streets of painted townhouses and flowering balconies. The cobblestoned lanes of Old San Juan pulse with world-class rum bars, ceviche stands, and rooftop restaurants serving the island's vibrant cocina criolla. La Fortaleza, the oldest executive mansion in the Western Hemisphere still in use, anchors the historic district. Florecer, the district's famed bioluminescent bay, glows emerald after dark. January through April offers the most idyllic conditions.

Jost Van Dyke is a tiny, uncommercialised island in the British Virgin Islands named after a Dutch privateer, celebrated for its pristine white-sand beaches, legendary beach bars, and barefoot Caribbean culture. Visitors should not miss savouring a Painkiller cocktail at the Soggy Dollar Bar on White Bay and exploring the granite grottos of The Baths on nearby Virgin Gorda. The dry season from December through April offers the most radiant sailing conditions and calm turquoise waters, making it the ideal window for a luxury small-ship call at this intimate Caribbean gem.

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.

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.

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.