Discover the best festivals and events in Key West!
From captivating theater performances and comedy shows to exhilarating fishing tournaments and literary seminars, our curated event listings offer unforgettable experiences year-round. Plan your perfect Key West getaway and immerse yourself in the vibrant local culture, entertainment, and island charm.
Femmes of Rock
FEMMES OF ROCK at Key West Theater: Electrifying Strings and Rock Legends Live FEMMES OF ROCK brings its internationally acclaimed, high-octane string rock experience to the Key West Theater for a ni...
Key West Theater with Anthony Rodia
Laugh Out Loud at Key West Theater with Anthony Rodia’s Comedy Show On Thursday, December 11, 2025, Key West Theater at 512 Eaton St transforms into a hub of hilarity as Anthony Rodia delivers his La...
Annual Schooner Wharf Bar Lighted Boat Parade
34th Annual Schooner Wharf Bar Lighted Boat Parade — Key West’s Nautical Holiday Spectacle Date: Saturday, December 13, 2025Time: 8:00 p.m.Location: Schooner Wharf Bar & Key West Historic Seaport...
Key West Triathlon 2025 at Higgs Beach
Key West Triathlon 2025 at Higgs Beach — Swim, Bike & Run in Paradise The Key West Triathlon 2025 takes place on Sunday, December 14, 2025, at the iconic Higgs Beach waterfront. Athletes from acr...
Running of the Elves 5k Run/Walk & Jingle Bell Mile
Run, Walk & Celebrate at Dante’s Key West Holiday 5K & Jingle Bell Mile Kick off the holiday season island-style at the Key West Holiday 5K & Jingle Bell Mile, where festive lights, tropi...
Ben Harrison Live at Key West Theater
Ben Harrison Live at Key West Theater – January 8, 2026 On Thursday, January 8, 2026, the Key West Theater at 512 Eaton Street welcomes back Ben Harrison, a celebrated storyteller, songwriter, and cu...
Robyn Schall's Holiday Extravaganza Tour
Robyn Schall Live at the Key West Theater — The Robyn Schall Experience Date: Friday, January 9, 2026Time: 8:00 PM (Doors Open 7:00 PM)Location: Key West Theater, 512 Eaton Street, Key West, Florida ...
David Nihill: Taking Tangents Tour
David Nihill Live at Key West Theater – January 2026 On Sunday, January 11, 2026, the Key West Theater welcomes back internationally acclaimed Irish comedian David Nihill for his brand-new show, Shel...
Los Lobos | Key West theater
Key West Theater Presents Los Lobos: A 50-Year Musical Legacy On January 13, 2026, Key West Theater at 512 Eaton St, Key West, FL, hosts Los Lobos, a legendary Chicano rock band celebrating 50 years ...
