11-Day Eastern Caribbean: Windward & Leeward Islands

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.

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.

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.

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.

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.

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.

Charlotte Amalie, the capital of St. Thomas, unfolds across a hillside of Danish colonial buildings and cobblestone alleys above one of the Caribbean's most celebrated natural harbors, its duty-free shops and waterfront markets reflecting three centuries of mercantile tradition. Beyond the vibrant town, the island's real splendor reveals itself at Magens Bay — a sheltered arc of powdery sand consistently ranked among the world's most beautiful beaches — and at Coral World Ocean Park, where underwater observatories and sea encounters delight. The Caribbean's reliably warm and sunny climate makes St. Thomas a compelling destination throughout the year.

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.

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.