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.

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.

Little Bay is a symbol of Montserrat's resilience after the 1997 Soufrière Hills eruption destroyed Plymouth. A new city now rises on the northern coast, amid lush hills, beaches, coral reefs, and humpback whales. Explore jungle trails, kayak the coast, and watch sunsets at beach bars honoring the island's musical heritage. Visit Plymouth's ruins and the Montserrat Volcano Observatory for stark views of the crater.

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.

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.

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.

Between the Dominican Republic mainland and Samaná Peninsula, Cayo Levantado is a jade jewel in sapphire seas. Walk ivory-white sands, cross crystal waters to adventures, and explore nearby rainforests, waterfalls, secret coves, and scenic trails. Paddle mangroves, cruise to soft beaches, and enjoy colorful houses, fresh fish, and rum punch sunsets.

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 the US Virgin Islands' mix of heritage and island charm: sparkly St. Thomas has a flawless capital with local culture, boutiques, Danish street names, pirate lore, historic landmarks, cable-car views, and Frenchtown's restaurants. Ferry to St. John for scenic beauty, diamond-sand beaches, clear blue water, and forest hikes. Caribbean warmth, Danish roots, and American influence make this a unique culture clash.

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.

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.