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.

St. John, the smallest US Virgin Island, is lined with quiet coves and hidden harbours. Relax on Trunk Bay's turquoise water and powder-soft sand. Virgin Islands National Park covers two-thirds of the island, protecting forested valleys, indigenous rock art, old sugar plantation ruins, and scenic hiking trails. Kayak the mangroves of Hurricane Hole or snorkel Maho Bay, where turtles and rays glide through clear water.

Pretty Point-à-Pitre sits between Guadeloupe's butterfly-like wing islets. Stroll leafy Victory Square, browse markets and boutiques, or visit the award-winning Memorial ACTe. Cross to Basse-Terre for rain forests, waterfalls, French fort ruins, and La Grande Soufrière volcano. Or head to Grand-Terre for multicolored beaches, Castle Point, and museums honoring Nobel-winning poet-diplomat Alexis Léger.

St Martin lets you visit two countries in one morning. Explore the little French capital with coral-colored houses, markets, boulangeries, and bistros, then relax on turquoise beaches and chic Orient Bay. Shop chocolate and cheeses in Dutch stores. Hike French slopes, visit Fort Amsterdam, go horseback riding, diving, or take a gyrocopter to see eco-sites rich in flora and fauna. St Martin is magnifique.

Enter a serene Bahamian paradise: an exclusive, eco-friendly island marine reserve and perhaps the world's most coveted escape. Snorkel, paddleboard, or boat over aquamarine waters; see marine life in its natural habitat; visit the marina, lighthouse, lagoon, and pastel buildings. Relax with a beachside massage, lazy lunch, rum cocktails, and powdery white sands shaded by palm leaves.

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.