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.

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.

Explore romantic St Lucia: hike the UNESCO-listed Pitons, soak in volcanic mud baths, relax on black sand beaches, visit botanical gardens, and trek tropical jungle plantations of banana, coconut, and mango. Cruise calm Caribbean or choppy Atlantic waters by catamaran, boat, or kayak, swim under waterfalls, watch whales, and savor fresh mahi mahi with local Piton beer.

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.

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.

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.

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.