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.

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.

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.

Slip into a tranquil, tropical paradise of sparkling waters, coral reefs and powder white beaches. Switch off and slowly shop, swim, snorkel and sip within the peace of sand, sea and sky. Sink into a beachside boulder-forming pool at The Baths, admire spectacular villas scattered on the Great Mountain, sit back on a safari bus ride or sunbathe aboard a catamaran. Prepare to be mesmerised by this softly lit, sun-drenched heaven.

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.