Annual Events in KW

Big events in Key West may be your reason for travel or reason to avoid the area during a particular timeframe. Key West is geographically small (only about 7 sq miles) so big celebrations like Pride or Fantasy Fest tend to take over the city. If attending an event is your plan, the party will be all around and a good time unavoidable! But if you are looking for peace and quiet, consider avoiding travel during these busy times.

This is by no means an exhaustive list, as KW is always looking for a reason to host a party, but some of the more popular events. For a complete list check out the Key West Events Calendar

• The Southernmost Regatta
  • Exhilarating action with a 30-year history, this January event is a big part of the Key West calendar
• Key West Literary Seminar
  • An annual 4-day event also in January bringing book lovers from around the world to this subtropical island
• Key West Food & Wine Festival
  • Another January event showcasing a vast range of wines and inventive cuisines.
• RokIsland Festival 
  • A new addition to the party lineup, where hair bands of the 80’s rule in January

• Conch Republic Independence Celebration
  • A lively annual event in April celebrating the eccentric good humor of Keys residents who in 1982 “ceded” from the US and declared independence as a sovereign nation known as the Conch Republic, and the source of this flag recognized by anyone who knows and loves KW. 
• Key West Pride Week
  • One of the biggest Pride celebrations in America, this four-day celebration in June celebrates love and diversity!
• The Hemingway Days Festival
  • A four-day celebration in July of Ernest Hemingway, his literary works, and his connection to Key West. You will see many Hemmingway lookalikes as there is a yearly contest, and a “running of the bulls” KW-style.
• Fantasy Fest
  • Occuring in mid to late October every year, this is exactly what it sounds like–a playground (largely for adults) for fun and fantasy. Tends to be busy and NSFW, and while there are family friendly events, this may not be the best time to travel (especially with kids) unless this is your intended itinerary.