Following paradisiacal Overseas Highway is a short-term affair (the drive can take as little as four hours), and great journey to tack on to a pre-existing plan to hit up Miami for Art Basel. Rent a convertible car and start in Key Largo, where the 113-mile-long series of bridges linking the Florida Keys begins. The starting point of this trip is a top snorkelling destination, so we recommend booking in a few hours to explore the shallow reefs at John Pennekamp Coral Reef State Park. From there, your focus should turn to food. Try conch fritters at Alabama Jack's and Iguana Bait beer at Florida Keys Brewing Co., with a stop along Islamorada for sunbathing on the beach. Your next traverse will be the Seven Mile Bridge, which straddles the turquoise Florida Strait and the Gulf of Mexico. This trip's final destination is Key West, the former home of Ernest Hemingway and the ideal spot for a couple of beachy days to cap things off.