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.

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.

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.

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.