Key West events are so much fun! There's always something going on in the Southernmost party city! So you're wondering what Key West things to do. Find what concert, musician, local bands and so much more on our Key West events party guide calendar. Our Party in Key West destination guide will make your visit to Key West the best ever!
Key West Events
Key West Event Calendar
Summer Fringe: Clouds Over the Sunshine Inn
Date(s): Jul 15–25, 2026Venue: Fringe TheaterCategory: Theater / FringeWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/summer-fringe-clouds-over-the-sunshine-inn
Hemingway Days & Hemingway Look-Alike Contest (2026)
Hemingway Days & Hemingway Look-Alike Contest (2026)
Hemingway Days & Hemingway Look-Alike Contest
Date(s): Jul 19–26, 2026Venue: Hemingway Days / Sloppy Joe'sCategory: Festival / LiteraryPhone: 305-797-0579Website: https://keywestlookalikes.com/
Summer Fringe: Clouds Over the Sunshine Inn
Date(s): Jul 15–25, 2026Venue: Fringe TheaterCategory: Theater / FringeWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/summer-fringe-clouds-over-the-sunshine-inn
Hemingway Days & Hemingway Look-Alike Contest (2026)
Hemingway Days & Hemingway Look-Alike Contest (2026)
Hemingway Days & Hemingway Look-Alike Contest
Date(s): Jul 19–26, 2026Venue: Hemingway Days / Sloppy Joe'sCategory: Festival / LiteraryPhone: 305-797-0579Website: https://keywestlookalikes.com/
Hemingway Days & Hemingway Look-Alike Contest
Celebrate Ernest Hemingway’s Key West legacy with literary events, contests, and island traditions.
Sloppy Joe’s 45th Annual Hemingway Look-Alike Contest
Hemingway look-alikes gather for one of Key West’s most iconic contests.
Hemingway Days & Hemingway Look-Alike Contest
Celebrate Ernest Hemingway’s Key West legacy with literary events, contests, and island traditions.
Sloppy Joe’s 45th Annual Hemingway Look-Alike Contest
Hemingway look-alikes gather for one of Key West’s most iconic contests.
Hemingway Days & Hemingway Look-Alike Contest
Celebrate Ernest Hemingway’s Key West legacy with literary events, contests, and island traditions.
Sloppy Joe’s 45th Annual Hemingway Look-Alike Contest
Hemingway look-alikes gather for one of Key West’s most iconic contests.
Hemingway Days & Hemingway Look-Alike Contest
Celebrate Ernest Hemingway’s Key West legacy with literary events, contests, and island traditions.