Key West Event Calendar

Events

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  • 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 look alike contest

    Hemingway Days & Hemingway Look-Alike Contest

    elebrate the adventurous lifestyle and literary talent of Ernest Hemingway, who called Key West home in the 1930s, with Sloppy Joe’s three-night Hemingway Look-Alike Contest — drawing up to 160 bearded contenders — and other enticing events. Attractions include the “Running of the Bulls” spoof, a high-energy storytelling competition, Hemingway–themed cocktail experiences, a Look-Alike film evening, a lively street fair, a salute to Hemingway’s angling exploits, and the finale of the Lorian Hemingway Short Story Competition. www.keywestlookalikes.com.

  • Key West Marlin Tournament

    Key West waters / tournament venues

    A major Key West fishing tournament held during Hemingway Days.

  • Key West Farmers Market at Truman Waterfront

    Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): Jul 23, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): Jul 23, 2026Venue: Comedy Key WestCategory: Music / Lunch ShowPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/burgers-buffet-tunes-a-tribute-show-at-comedy-key-west

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): Jul 24, 2026Venue: Comedy Key WestCategory: Comedy / HistoryPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/hemingway-in-a-funny-way-at-comedy-key-west

  • Summer Bingo @ Key West Theater

    Key West Theater 512 Eaton Street, Key West, Florida, United States

    Summer Bingo returns to Key West Theater for a fun midweek event.

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