Explore America's oldest city for Caribbean history, Spanish culture, and the American dream. Wander Old San Juan's alleys past centuries-old forts and colorful colonial buildings. Learn to move to salsa and reggae, shop boho streets or luxe boutiques for artisan goods, designer pieces, and hand-rolled cigars. Enjoy world-class surfing, a tropical rainforest, a private rum cocktail tasting, and empanadas. End on beautiful beaches with crystal-clear water and maybe one last rum cocktail.

Philipsburg is the capital of Dutch Sint Maarten on the island shared with French Saint Martin. Set beside Great Bay, its colorful streets are lined with Dutch shops selling chocolates, cheeses, and luxury goods. Enjoy kayaking in blue waters, reef diving, horseback rides on plantation trails, casinos, or golf by the sea. Every moment feels royal.

In dainty Terre-de-Haute, diminutive sibling of Guadeloupe and queen of the Îles des Saintes, French charm and Caribbean culture are woven together in laid-back towns and sleepy fishing villages. High above, Fort Napoleon and Le Chameau peak are flanked by fragrant forests of fern and frangipani, overlooking picture-perfect landscapes bathed in golden sunlight and sailboats afloat on gin-clear bays.

Nestled in a caldera horseshoe, with candy-coloured houses spilling to the water, this natural harbour is often considered the Caribbean's prettiest. Explore the Georgian Carenage, market stalls, Fort George, the cathedral and Anglican church rebuilt after the 2004 hurricane, and the House of Chocolate devoted to Grenada's cacao trade. Then head inland for lush hikes to waterfalls, or north on a spice journey, with nutmeg scenting the air.

Explore romantic St Lucia: hike the UNESCO-listed Pitons, soak in volcanic mud baths, relax on black sand beaches, visit botanical gardens, and trek tropical jungle plantations of banana, coconut, and mango. Cruise calm Caribbean or choppy Atlantic waters by catamaran, boat, or kayak, swim under waterfalls, watch whales, and savor fresh mahi mahi with local Piton beer.

Puerto Plata, the "Silver Coast" queen, is prized for cloud-shrouded peaks and gleaming beaches. Once plundered by pirates, it still invites you to storm the 16th-century Fortaleza San Felipe. Today it lures visitors with aged rum, cigars, and chocolate. Adventurers can ride to Pico Isabel de Torres (793 m/2,602 ft), off-road to Damajagua Waterfalls, or kite-surf, catamaran, and zip-line over the ocean. Save time for a beach club and coconut cocktails.

Miami and South Beach blend iconic movie backdrops with Latin American culture: Art Deco streets, Wynwood's murals, and Little Havana's café cortadito, sugarcane juice, beer, ice cream, dominoes, cigars, and politics. Add salsa, designer shopping, speedboats, and the Everglades for rare wildlife.

Experience the US Virgin Islands' mix of heritage and island charm: sparkly St. Thomas has a flawless capital with local culture, boutiques, Danish street names, pirate lore, historic landmarks, cable-car views, and Frenchtown's restaurants. Ferry to St. John for scenic beauty, diamond-sand beaches, clear blue water, and forest hikes. Caribbean warmth, Danish roots, and American influence make this a unique culture clash.

Experience Anguilla's blissfully quiet, laid-back island life: roam with wildlife, learn its quirky history, and explore Katouche Cave. Take a guided quad bike tour for a glimpse of island life, then sail across electric-blue seas to remote Little Bay, where jagged cliffs meet pristine sand. Kayak or paddleboard to secluded coves, and unwind with cocktails and butter-soaked grilled lobster at beach bars with the softest white sand underfoot.

Embrace Martinique's natural joie de vivre: volcanic in origin, Gallic in heritage, Creole at heart. Explore old sugar plantations, rum distilleries, cocoa farms, and the St Pierre ruins beneath still-smouldering Mont Pelée. Chase Saut du Gendarme, roam the 10-million-year-old Caravelle Peninsula, walk northern dusky beaches, and visit Le Carbet, made famous by Gauguin. Sip the national punch and discover the magic of its Creole-French blend.

Formed by volcanoes, St Kitts has rich, fertile soil and lush rainforest. Hike Mount Liamuiga to its mile-wide crater, or descend to smell the sulphur. Try a scenic train ride, sailing, cooking class, sky-safari zip-line, or batik workshop. Visit sugarcane plantations, the Narrows, and UNESCO Brimstone Hill Fortress for island views. Small in size, big on charm.

Philipsburg is the capital of Dutch Sint Maarten on the island shared with French Saint Martin. Set beside Great Bay, its colorful streets are lined with Dutch shops selling chocolates, cheeses, and luxury goods. Enjoy kayaking in blue waters, reef diving, horseback rides on plantation trails, casinos, or golf by the sea. Every moment feels royal.

Explore America's oldest city for Caribbean history, Spanish culture, and the American dream. Wander Old San Juan's alleys past centuries-old forts and colorful colonial buildings. Learn to move to salsa and reggae, shop boho streets or luxe boutiques for artisan goods, designer pieces, and hand-rolled cigars. Enjoy world-class surfing, a tropical rainforest, a private rum cocktail tasting, and empanadas. End on beautiful beaches with crystal-clear water and maybe one last rum cocktail.