Miami to San Juan

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.

Charlotte Amalie, the Danish-founded capital of the U.S. Virgin Islands on St. Thomas, is a Caribbean port of rare historical depth where colonial architecture, world-class duty-free shopping, and volcanic hillside panoramas converge around one of the Atlantic's most striking natural harbors. No visit is complete without climbing the historic 99 Steps for sweeping harbor views and taking a ferry to St. John's pristine Virgin Islands National Park. The dry season from December through April offers the most luminous skies and calmest seas, coinciding perfectly with peak cruise season.

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.

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.

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.

Tortola, the largest island in the British Virgin Islands, is a captivating blend of history, culture, and natural beauty. Must-do experiences include savoring Anegada lobster and exploring the stunning Baths on Virgin Gorda. The best time to visit is during the dry season from December to April, when the weather is perfect for beach lounging and island adventures.

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.