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.

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.

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".

Take your time-happy hour here feels endless. Soak up the island's history amid turquoise seas and sapphire skies. Explore salt flats, old-world villages, conch, and the lighthouse. Snorkel or dive in crystal-clear waters, then enjoy rum punch on a catamaran. Or simply relax under bougainvillea shade and savor the island's slower pace.

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.