Key West, United States

Key West sits at the end of the road, literally. Mile Marker Zero of U.S. Route 1 marks the southernmost point of the continental United States, and the 113-mile drive from Miami along the Overseas Highway, one of the great American road trips, is the journey that gets you there. The highway leaps across 42 bridges, including the spectacular Seven Mile Bridge, a ribbon of concrete suspended above the shimmering blue-green waters of the Florida Keys. By the time you arrive in Key West, you have left mainland America behind in more than geography. This two-by-four-mile island at the tail end of the Florida Keys chain operates on its own terms: a free-spirited, sun-bleached, culturally layered place that has attracted pirates, wreckers, cigar makers, shrimpers, writers, artists, and misfits for two centuries.

The literary and artistic heritage of Key West is legendary. Ernest Hemingway lived and wrote here from 1931 to 1939, producing some of his greatest works, including To Have and Have Not and parts of For Whom the Bell Tolls, in the study of his Spanish colonial home on Whitehead Street. The house is now a museum, and its grounds are populated by roughly sixty polydactyl cats, descendants of a six-toed cat given to Hemingway by a ship captain. Tennessee Williams, Robert Frost, Elizabeth Bishop, and Jimmy Buffett all called Key West home at various points, drawn by the same qualities that still define the place: warm light, cheap rent (once upon a time), a tolerance for eccentricity, and a pace of life measured in sunsets rather than deadlines. The nightly Sunset Celebration at Mallory Square, where jugglers, musicians, acrobats, and psychics gather as the sun drops into the Gulf of Mexico, has been a Key West tradition since the 1960s.

A flower from Bauhinia blakeana in Key West, Florida© Ianare, CC BY-SA 3.0, via Wikimedia Commons

The cultural fabric of Key West is woven from an unusually diverse set of threads. The Bahama Village neighborhood preserves the heritage of Bahamian immigrants who came to work in the wrecking and sponging industries in the nineteenth century. The Cuban influence is equally strong, a legacy of the cigar factories that once made Key West the wealthiest city per capita in the United States. Cuban coffee, pressed in tiny stovetop espresso makers and served sweet and strong, is the fuel of daily life, and Cuban mix sandwiches, pressed on Cuban bread with ham, pork, Swiss cheese, pickles, and mustard, are the island's signature lunch. Duval Street, the main commercial strip running from the Gulf to the Atlantic, is the island's social backbone: a mile-long parade of bars, galleries, restaurants, and souvenir shops that ranges from refined to raucous depending on the hour and your block.

The best time to visit Key West is from November through April, when temperatures hover between 65 and 80 degrees Fahrenheit, humidity is moderate, and the chance of rain is low. The winter months also bring the best fishing, with tarpon, bonefish, and permit drawing fly-fishing enthusiasts from around the world. Summer is hot and humid, with temperatures in the upper 80s and frequent afternoon thunderstorms, though the pace slows, prices drop, and the island takes on a more local character. Hurricane season runs from June through November, with September and October the peak risk months. Key West has been hit by several major hurricanes over the centuries, most devastatingly in 1846 and during Hurricane Irma in 2017, which caused significant damage to the Lower Keys.

Estevez Photo Studio, 604 Duval Street, Key West Florida. Exterior view with signage by Arthur Rothstein, January 1938. Border cropped, contrast adjusted, and converted from tif to jpg.© Arthur Rothstein, Public domain, via Wikimedia Commons

The waters around Key West are part of the Florida Keys National Marine Sanctuary, protecting one of the largest barrier reef systems in the world. Snorkeling and diving the reef is a must, with sites ranging from shallow coral gardens teeming with parrotfish, angelfish, and sea fans to deeper wrecks like the USNS Vandenberg, a 523-foot former military vessel intentionally sunk in 2009 to create an artificial reef. Fort Zachary Taylor State Park offers the best beach in Key West, a rocky-bottomed swimming area with excellent snorkeling right off shore and a Civil War-era fort worth exploring. For history buffs, the Harry S. Truman Little White House, where the president spent 175 days of his presidency, and the Key West Lighthouse provide quieter alternatives to the Duval Street scene. Rent a bicycle, the preferred mode of transport, pedal through the shaded lanes of Old Town past gingerbread Victorian houses draped in bougainvillea, and let the island's unhurried rhythm set the tempo. Key West has always been a place for people who do not quite fit anywhere else, and that spirit of welcome remains its greatest charm.