14-Day Leeward Island Jewels

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.

Road Bay is the anchorage for Anguilla, whose sixteen miles harbor some of the world's finest beaches — including Shoal Bay East's two-mile masterpiece — and a dining scene that defies the island's modest population of fifteen thousand. Visit December through April via Ponant or Windstar for the Caribbean's most convincing synthesis of perfect sand, exceptional cuisine, and the genuine exclusivity that comes from having no deep-water cruise port.

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.

Ocho Rios is Jamaica's waterfall-blessed north coast resort town, home to the iconic Dunn's River Falls and Ian Fleming's GoldenEye estate where every Bond novel was written. Must-dos include climbing Dunn's River Falls, tasting jerk at Scotchies, and sampling Blue Mountain coffee. December through April offers the driest, most comfortable conditions.

Dominica is the Caribbean's Nature Island, a volcanic wilderness of rainforest-covered peaks, the otherworldly Boiling Lake, year-round sperm whale watching, and the indigenous Kalinago community. Must-do experiences include hiking to the Boiling Lake, snorkelling the bubbling Champagne Reef, and tasting callaloo soup. November through June is driest, with February through April offering the most comfortable conditions for hiking.

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.

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.

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.

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.