Events in the Florida Keys
We have gathered local Florida Keys events to help you find fun things to do during your stay. Browse the calendar below for festivals, live music, waterfront celebrations, family-friendly activities, food events, fishing tournaments, holiday happenings, and more.
From Key Largo and Islamorada to Marathon, Big Pine Key, and Key West, there is always something happening in the Keys. Use this calendar to plan around local favorites, discover seasonal events, and make the most of your Florida Keys vacation.
Hemingway Days and Look-Alike Contest
- Location: Sloppy Joe's Bar
The Hemingway Look-Alike Contest is one of Key West’s most iconic and playful celebrations, honoring the life and larger-than-life personality of Ernest Hemingway. Held annually, the event brings together participants from around the world who compete to be crowned “Papa,” judged on both their resemblance to Hemingway and their ability to capture his spirit.
Festivities also include the crowd-favorite “Running of the Bulls,” a humorous Key West twist featuring wooden bulls on wheels. With lively events, friendly competition, and a strong sense of community, this celebration is a fun, can’t-miss experience for visitors and locals alike.
