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.

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.

An adrenaline rush awaits. Swim with stingrays. Zip-line through lush forests. Walk across a gorge on a scenic suspension bridge. Sip excellent aged rums. Taste the island with a chef. Or stroll St. John's old town to tour cottages laden with cheerful fretwork. Explore British forts atop Shirley Heights and Goat Hill. Then rest and rejuvenate at one of the snow-white beaches.

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.

Mango-scented reveries on flour-soft beaches. Tinkling ice cubes in rummy cocktails. Rainbow marine life in crystalline coral gardens. Welcome to Catalina Island, an earthly paradise where trails meander through fragrant forests and merengue rhythms drift on the breeze. Fortune awaits in the sunken wreckage of Captain Kidd's ship, home of silent sponges and sentinel seahorses, an underwater kingdom awaiting discovery.

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.