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.

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.

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.

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".

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.

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.

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.

La Romana offers tranquil, cosmopolitan-tropical escape. See Altos de Chavón, a replica 16th-century Tuscan village with art and fashion studios and a 5,000-seat limestone amphitheater. Stay at Casa de Campo, a luxury resort famed for golf, dining, and polo. Dive from Bayahibe Beach or visit Cotubanamá National Park for dolphins, manatees, and colorful birds.

Named for a Dutch pirate who once encamped here, Jost Van Dyke is a tiny jewel of lush scenery and beautiful beaches. Hike or take a water taxi to Bubbly Pool, a natural jacuzzi where high-tide waves crash through a crevasse. Relax on White Bay's powder-fine sand, swim its turquoise shallows, and try the island's iconic Painkiller, a dark rum and coconut cocktail created in the 1970s at the Soggy Dollar Bar.

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".

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.