Every evening visitors gather at Mallory Square for a Key West tradition known as the Sunset Celebration. Spectators witness local entertainers and artists display their talents and crafts. For those who aren't sure, it takes place ONCE a day.
Ernest Hemingway fans celebrate the late author’s literary accomplishments and colorful Key West lifestyle each July. The annual Hemingway Days festivities salute the legacy of the Nobel Prize winner who lived and wrote on the island for most of the 1930s. Events include the famed Hemingway® Look-Alike Contest, prose and poetry readings, the tongue-in-cheek “Running of the Bulls,” symposium presentations and a film evening, a look-alike “party” on Hemingway’s July 21 birthday, running and paddleboarding challenges, a lively street fair and a high-stakes three-day marlin tournament recalling his passion for Florida Keys angling.
Swim for Alligator Lighthouse
Hundreds of solo and relay-team swimmers race to conquer the annual Swim for Alligator Lighthouse, a unique open-ocean endurance swimming challenge in Atlantic waters off Islamorada in September. Individuals and two-, three- and four-person teams have up to seven hours to complete the 8-mile roundtrip course. Participants must show proof of completing a prior 1,650-meter or 1-mile swim in 35 minutes or less to compete as an individual.