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  • Doug Benson at Comedy Key West

    Date(s): May 1–2, 2026Venue: Comedy Key WestCategory: ComedyPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/doug-benson-at-comedy-key-west

  • You’re a Good Man, Charlie Brown

    Date(s): May 1–3, 2026Venue: Red Barn TheatreCategory: Theater / MusicalPhone: 305-296-9911Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/youre-a-good-man-charlie-brown-red-barn-theatre

  • KWSF Saturday Bloody Mary Bash

    Date(s): May 2, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352914

  • One Night of Queen

    Date(s): May 3, 2026Venue: Tennessee Williams TheatreCategory: MusicPhone: 305-296-1520Website: https://twstages.com/onenightofqueen

  • KWSF Sunday All Star Encore

    Date(s): May 3, 2026Venue: Key West TheaterCategory: Music / FestivalPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1352919

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): May 7, 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): May 7, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Key West Playwrights Festival

    Date(s): May 7–8, 2026Venue: Williams HallCategory: TheaterWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/key-west-playwrights-festival

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): May 8, 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

  • Happy Birthday Harry!

    Date(s): May 8, 2026Venue: Truman Little White HouseCategory: History / CommunityPhone: 305-294-9911Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/happy-birthday-harry

  • Key West Paddle Classic

    Date(s): May 9, 2026Venue: Florida Keys Waterman Co.Category: Sports / OutdoorWebsite: https://www.floridakeyswatermancompany.com/keywestpaddleclassic

  • Threads of Love: A Mother’s Legacy Through Dance

    Date(s): May 10, 2026Venue: Tennessee Williams TheatreCategory: DancePhone: 305-296-1520Website: https://www.etix.com/ticket/p/31719458/threads-of-lovea-mothers-legacy-through-dance-key-west-tennessee-williams-theatre

  • 10,000 Maniacs

    Date(s): May 10, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1304993

  • 40th Annual Queen Mother Pageant

    Date(s): May 11, 2026Venue: Key West TheaterCategory: Pageant / LGBTQ+Phone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1408898

  • Key West Farmers Market at Truman Waterfront

    Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): May 14, 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): May 14, 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

  • Tri Knot to Rock

    Date(s): May 15, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1402575

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): May 15, 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

  • DanceWorks 23!

    Date(s): May 16–17, 2026Venue: Tennessee Williams TheatreCategory: DancePhone: 305-296-1520Website: https://www.etix.com/ticket/p/90215248/danceworks-23-key-west-tennessee-williams-theatre

  • Key West Farmers Market at Truman Waterfront

    Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): May 21, 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): May 21, 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): May 22, 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

  • Salute to Service 5K Run & Walk

    Date(s): May 24, 2026Venue: The Marker ResortCategory: Sports / CommunityWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/salute-to-service-5k-run-walk