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.

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".

Still quiet and Eden-like, Saint Croix-the largest U.S. Virgin Island-retains a rare underdeveloped charm. Expect protected reefs, rum distilleries, frangipani, cacti, and beautiful beaches, plus music, quirky shops, Dutch forts, and lush botanical gardens. Explore Buck Island Reef National Monument, hailed by National Geographic as "one of the world's best beaches," and stroll Frederiksted and Christiansted, shaped by seven ruling flags and the enduring spirit of the Carib and Taino peoples.

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.