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.

A tropical utopia in the British Virgin Islands: soaring peaks for climbing, waves for surfing, wrecks for snorkelling, and cocktails with local rum. Around Road Town are brightly coloured colonial-era buildings; try Pusser's Painkiller Bar, then head to Sage Mountain. Zip-line, dive coral lagoons, 4x4 jungle trails, relax on postcard-perfect beaches, or sail by catamaran to uninhabited islands.

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.

Mingle amongst other discerning guests on this French isle that exudes relaxed glamour. Wander along secluded beaches, harbourside Creole huts, drop into bohemian bars and snorkel gently through warm turquoise waters. Visit La Tourmente, the peaceful salt ponds and admire uninterrupted views on a local boat trip. And as you sip your second (or third) glass of champagne to the lull of the gentle waves, it might be time to learn the French for "paradise found".

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.

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.