Party In Key West

Sloppy Joe’s 45th Annual Hemingway Look-Alike Contest
2026-07-21 00:00 - 2026-07-26 00:00 (America/New_York) | Sloppy Joe’s
The Hemingway Look-Alike Contest at Sloppy Joe’s is a spirited tribute to Papa Hemingway during Hemingway Days.

Hemingway Days & Hemingway Look-Alike Contest
2026-07-21 00:00 - 2026-07-26 23:59
Hemingway Look-Alike Contest and Festival
July 21-26, 2026 in Key West, FL
Celebrate 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.
Hemingway Days brings literary events, street festivities, a look-alike contest, and Key West traditions honoring Ernest Hemingway.
Media Contact: Carol Shaughnessy
Phone: 305-797-0579
E-mail: media@keywestlookalikes.com

Sloppy Joe’s 45th Annual Hemingway Look-Alike Contest
2026-07-21 00:00 - 2026-07-26 23:59

Summer Bingo @ Key West Theater
2026-07-22 00:00, 2026-07-22 00:00 - 02:00, 2026-07-29 00:00, 2026-07-29 00:00 - 02:00 | Key West Theater, 512 Eaton Street, Key West, Florida, 33040, United States
A summer bingo night at Key West Theater, offering an easygoing evening of games and local entertainment.

Key West Marlin Tournament
2026-07-22 00:00 - 2026-07-25 00:00 | Key West waters / tournament venues
Anglers compete in the Key West Marlin Tournament, one of the island’s signature summer fishing events.

Burgers & Buffet Tunes
2026-07-23
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
2026-07-23
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

Hemingway in a Funny Way
2026-07-24
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

37th Anniversary Hemingway 5K Sunset Run & Key West Beach N’ Beer Mile
2026-07-25 00:00 - 2026-07-26 00:00 | Southernmost Point area
Runners celebrate Hemingway Days with a 5K sunset run and Key West Beach N’ Beer Mile.

Lobster Mini Season
2026-07-29 00:00 - 2026-07-30 00:00 | Florida Keys waters
A beloved Florida Keys tradition as recreational divers and boaters head out for the annual two-day spiny lobster mini season.

Lobster Mini Season
2026-07-29 00:00 - 2026-07-30 23:59

Burgers & Buffet Tunes
2026-07-30
Weekly Thursday tribute lunch show.
Date(s): Jul 30, 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
2026-07-30
Recurring market date listed on Marketspread schedule for the Truman Waterfront market.
Date(s): Jul 30, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

‘Unspoken Bond’ Documentary Screening
2026-07-31 00:00, 2026-07-31 00:00 - 02:00 | Key West Theater, 512 Eaton Street, Key West, Florida, 33040, United States
A special documentary screening event at Key West Theater.
