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.

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.

Philipsburg is the capital of Dutch Sint Maarten on the island shared with French Saint Martin. Set beside Great Bay, its colorful streets are lined with Dutch shops selling chocolates, cheeses, and luxury goods. Enjoy kayaking in blue waters, reef diving, horseback rides on plantation trails, casinos, or golf by the sea. Every moment feels royal.

Funchal's ancient streets tumble down the hills. Ride the cable car to Monte Palace's exotic gardens, where peacocks roam above the Atlantic. Descend in a wicker sleigh guided by Carreriros in white and straw hats, a tradition since the mid-1800s. Sip amber Madeira overlooking Praça do Município, then explore lush cloud forests, hiking trails, and black-sand beaches below jungle-covered cliffs.

Step back in time in Cádiz, where cobbled streets, horse-drawn carriages, tapas, and Andalusian horses evoke Spain's soul. Tour sherry wineries in Jerez, then flamenco in Seville. Explore baroque churches, palaces, Gothic cathedrals, aristocratic mansions, and medieval buildings. With three UNESCO World Heritage sites, Cádiz is truly inspiring.

Enjoy the epitome of Spanish charm. Slowly discover Andalusian riches to reveal Picasso's birthplace, the Alhambra in Granada, Mezquita in Cordoba and the Ronda valley. Explore ancient heritage sites, dance the flamenco, dare to hike the Caminito del Rey trail and delve into white villages sprinkled amongst mango groves and avocado orchards. Sip cocktails by day and sangria by night. And as you watch the sun slip down, reflect upon this gateway of delights.

Barcelona blends vibrant energy with Catalan tradition: explore the Gothic Quarter and Gaudí's architecture, enjoy tapas and cava in plazas and cafés, relax at the beach, shop along Passeig de Gràcia, and end the night in bohemian bars on La Rambla. A stylish city full of character.