Strung across the water like a necklace of coral islands, the Florida Keys blend turquoise shallows, laid-back island style and some of the best sunsets in America. This is barefoot luxury at its finest, from private fishing charters to waterfront suites at the end of the road.

Begin in Key Largo and Islamorada, where the only living coral barrier reef in the continental U.S. offers world-class snorkeling and diving, and the flats are renowned for guided fly-fishing for bonefish and tarpon. Drive the legendary Overseas Highway across the Seven Mile Bridge to Marathon, then continue to Key West, where Hemingway’s old haunts, colorful Victorian architecture, and Mallory Square’s nightly sunset celebration create an atmosphere found nowhere else. A seaplane flight to Dry Tortugas National Park brings you to a 19th-century fort surrounded by pristine reef, a day trip that feels a world away. Throughout, stays at oceanfront resorts and an exclusive private-island retreat are paired with fresh stone crab, grilled hogfish, and the perfect slice of key lime pie.