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.
Key West Women Fest
- Location: Various locations in Key West
Womenfest Key West | September 2–6, 2026
Celebrate connection, creativity and community during Womenfest Key West, a five-day celebration for women set against the colorful backdrop of Key West. This year’s theme, “Lost Women in the Arts,” shines a light on women’s creativity and the artists, performers and visionaries finding — or reclaiming — their voices.
The Labor Day weekend lineup includes live music and entertainment, themed parties, poolside gatherings, a sunset sail, art experiences, tours, drag performances and plenty of opportunities to mix, mingle and enjoy the island. Whether you come with friends or make new ones along the way, Womenfest pairs Key West’s welcoming spirit with five days of fun, self-expression and celebration.
