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.

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".

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.

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.

Key West may sit at Florida's southern tip, but it starts the real laid-back life. Closer to Cuba than Miami, this last chain of coral islands is known for history, culture, fishing, cuisine, and candy-colored homes. Surf, snorkel, shop by appointment, and enjoy a private seafood tasting. Ride the Old Town Trolley, visit Hemingway's quirky house, see 50+ butterflies at the Butterfly & Nature Conservatory, and watch flamingos. Key West isn't just a beach town-it's a way of life.

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.