Key West Event Calendar

Events for July 23, 2026

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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.

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

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

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