Just 90 miles from Cuba, the island of Key West is the southernmost point of the continental United States and the most-populated island in the Florida Keys. Once a base of operations against pirates, Key West later rose to fame as an enclave for artists and writers including Robert Frost, Winslow Homer, Tennessee Williams and perhaps its most famous resident, Ernest Hemingway. The Keys became linked with the mainland in 1912 with the completion of the short-lived Henry Flagler’s railroad which was abandoned after a hurricane in 1935. The railroad was replaced a few years later with the 123-mile overseas highway that still stands today. The island’s small size makes it easy to explore on foot, especially for those just passing through for a day on a cruise ship (as I was recently). But the Conch Republic’s relaxed charm and fascinating history are likely to have you wishing you could stay much longer.