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.

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".

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".

Formed by volcanoes, St Kitts has rich, fertile soil and lush rainforest. Hike Mount Liamuiga to its mile-wide crater, or descend to smell the sulphur. Try a scenic train ride, sailing, cooking class, sky-safari zip-line, or batik workshop. Visit sugarcane plantations, the Narrows, and UNESCO Brimstone Hill Fortress for island views. Small in size, big on charm.

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.

Providenciales ("Provo") is the laid-back, luxe jewel of the Turks and Caicos: a low-lying cay ringed by coral and pristine beaches, with Grace Bay Beach and Provo Golf Club as highlights. Charter a boat to a remote island for a perfect sandbar, lunch on conch at Da Conch Shack, and explore the blue hole, dry cave system, and dramatic Wall. Best of all, just slow down and enjoy paradise.

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.

Soak up the ultimate wellbeing experience at a real life "Nature Island." Oxygenate in lush rainforests, revive under waterfalls, convene in thermal sprint waters, and detox in volcanic mud baths. Trek Morne Trois Pitons National Park, a UNESCO jewel with the Mother Nature's rarest flora and fauna. Stir-up true Caribbean soul food; taste callaloo soup; sip spiced rum; and learn how herbs can heal. To cap it all, you can even snorkel in the bubbles of uber-healthy Champagne Reef.

Channel Robinson Crusoe on remote Bequia: secret lagoons, castaway picnics, and warm blue waters for snorkeling. Feel the sweet Bequia breeze and its colonial history, then relax at Princess Margaret Beach. Climb Mount Peggy for views of St. Vincent. Stroll Belmont Boardwalk to Market Beach for hand-whittled mahogany boat models, then Port Elizabeth's catwalk for nutmeg ice cream. Visit the turtle sanctuary for hawksbills or ferry to Mustique, a favorite royal getaway.

Gently arrive in Barbados's vibrant capital, rich in history and architecture, and soak up its laid-back West Indian vibe. Follow the slow Bajan rhythm: surf, snorkel, and watch for turtles in warm blue waters. Explore Harrison's Cave, St Nicholas Abbey, and zipline above tropical flora. Then unwind on pastel pink, palm-lined beaches, where cocktail hour never ends and rum flows freely.