Above: The exterior of a cottage at The Gardens Hotel in Key West, Florida

Traditionally, Key West was one of those end-of-the-world places that attracted those who were keen to get away from it all. (I always get a kick out of seeing the signs for mile 0 that mark the beginning and end of Route 1.) For many years, it was a refuge for artists and writers — most famously, Ernest Hemingway, but also Tennessee Williams, John Hersey and Elizabeth Bishop. More recently, Key West acquired an off-putting reputation as a venue for vacationing college students, and the main thoroughfare, Duval Street, still has a stretch of a few blocks that can be politely described as raffish. Lately, however, there has been an influx of well-heeled retirees, who have restored cottages and raised the prevailing tone.

Join Andrew Harper today to continue reading our exclusive content.
Above: The exterior of a cottage at The Gardens Hotel in Key West, Florida

Read More from Our Trip:

Key West Restaurants The Cottage Hotels of Key West Two Historic Houses on Key West Superlative Seafood at Palm Beach Restaurants Tropical Retreats in Palm Beach Palm Beach Museums Founded by American Industrialists