Calendar of Special Events in Key West

Fantasy Fest is, of course, our major annual event. But there are others throughout the year, almost always something special going on!  In addition to the annual festivals and events, there are always plenty of unique attractions throughout the year.  For a detailed listing, visit the Florida Keys Tourist Development Council’s official website.


  • Key West Literary Seminar
  • Key West Food & Wine Festival
  • OIRF Tour of Homes & Gardens
  • Sculpture Key West (ongoing through April)
  • Premier Racing Sailboat Regatta
  • Live Theater Season


  • OIRF Tour of Homes & Garden
  • Old Island Days Art Festival
  • Civil War Days Heritage Festival
  • Live Theater Season


  • OIRF Tour of Homes & Garden
  • Annual Hospitality Open (golf)
  • St. Patrick’s Day Bar Stroll
  • Key West Fishing Tournament kick-off (runs through November)
  • Live Theater Season


  • 7-mile Bridge Run
  • World Sailfish Championship
  • Conch Republic Independence Celebration
  • Taste of Key West showcasing Key West’s world-class restaurant fare
  • Live Theater Season


  • Songwriters Festival
  • Key West Paddleboard Classic
  • Cinco de Mayo
  • KW Ladies Dolphin Championship
  • Memorial Day Weekend — hello, Summertime!
  • Live Theater Season


  • Pridefest
  • FKCC Swim Around Key West
  • South Florida Symphony’s Chamber Music Series begins


  • Independence Day (picnic and fireworks)
  • Key Lime Festival
  • Mel Fisher Days
  • Hemingway Days
  • Key West Fishing Tournament
  • Del Brown Permit Tournament
  • Bacardi Oakheart KW Marlin Tournament
  • Lobster Mini-season


  • Lobster Fest
  • Tropical Heat
  • Mystery Writers KW Fest



  • Labor Day Weekend — so long, Summertime!
  • Key West Brewfest
  • Women Fest


  • SoMo Marathon & Half-Marathon
  • Goombay
  • Zombie Bike Ride
  • Fantasy Fest


  • Meeting of the Minds (Parrotheads)
  • Super Boat World Championship Races
  • Key West Film Festival
  • Art!  Key West! Festival


  • KW Bight Before Christmas Holiday Celebration
  • Key West Holiday Parade
  • Lighted Boat Parade
  • Holiday Tour of Homes
  • New Year’s Eve