15-Day Southern Caribbean in Depth

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.

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.

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.

Saint Kitts, Saint Kitts and Nevis, delivers the Caribbean at its most authentic—stunning waters, vibrant culture, and cuisine that blends African, European, and indigenous traditions into something boldly distinctive. Don't miss the local food scene and the exceptional snorkeling. Best experienced December through April, during the dry season when skies are clearest and seas are calmest. Cruise lines including Cunard feature this port on their most compelling itineraries. Whether you have a few hours or a full day, the port rewards exploration at every pace and in every direction.

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.

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.

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.

Montserrat is a volcanic Caribbean island where the buried capital of Plymouth contrasts with the lush, resilient community rebuilt around Little Bay in the north. Must-dos include viewing Plymouth's ruins from the exclusion zone, hiking the Centre Hills cloud forest, and tasting goat water stew. December through May brings dry weather and the clearest volcano views.

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.

Saint Kitts, Saint Kitts and Nevis, delivers the Caribbean at its most authentic—stunning waters, vibrant culture, and cuisine that blends African, European, and indigenous traditions into something boldly distinctive. Don't miss the local food scene and the exceptional snorkeling. Best experienced December through April, during the dry season when skies are clearest and seas are calmest. Cruise lines including Cunard feature this port on their most compelling itineraries. Whether you have a few hours or a full day, the port rewards exploration at every pace and in every direction.

Spanish Town is the laid-back capital of Virgin Gorda in the British Virgin Islands, gateway to the Baths—a labyrinth of cathedral-sized granite boulders, grottoes, and turquoise tide pools that is one of the Caribbean's natural wonders. Must-dos include exploring the Baths, sailing the North Sound, and grilling fresh lobster at a waterfront restaurant. November through May offers the best weather, with steady trade winds and temperatures in the comfortable seventies and eighties.

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.