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  • A Rock Sails By

    Date(s): Apr 21–25, 2026Venue: Red Barn TheatreCategory: TheaterPhone: 305-296-9911Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/a-rock-sails-by-at-red-barn-theater

  • Conch Republic Independence Celebration

    Festival began Apr 17, 2026; included here because it overlaps the requested date range. Date(s): Apr 21–26, 2026 Venue: Conch Republic / Key West Category: Festival Phone: 305-296-0213 Website: https://conchrepublic.com/

  • Dark Night of the Soul

    Date(s): Apr 22–25, 2026Venue: Key West International Dance CompanyCategory: Dance / TheaterWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/key-west-international-dance-company-dark-night-of-the-soul-1

  • Tony V at Comedy Key West

    Date(s): Apr 22–25, 2026Venue: Comedy Key WestCategory: ComedyPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/tony-v-at-comedy-key-west

  • Art from the Attic: Art Show and Sale

    Arts & cultural listing notes public reception on Apr 22 and sale dates through May 8. Date(s): Apr 22–May 8, 2026Venue: Key West Woman's Club / McKee FundCategory: Arts / […]

  • Graham Nash

    Date(s): Apr 25, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1210656

  • Ocean Fest

    Date(s): Apr 25, 2026Venue: Mote Marine LaboratoryCategory: Festival / FamilyWebsite: https://mote.org/oceanfest

  • Bubbles, Baubles, and Bling – Oh My!

    Date(s): Apr 26, 2026Venue: Waterfront PlayhouseCategory: Theater / FundraiserPhone: 305-294-5015Website: https://www.onthestage.tickets/show/waterfront-playhouse/69d5691b39888c3830cd4f63

  • Graham Nash

    Date(s): Apr 26, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1210693

  • Where’s Dave Band

    Date(s): Apr 27, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1253418

  • Long Live Lambada!

    Date(s): Apr 28–30, 2026Venue: Tennessee Williams TheatreCategory: DancePhone: 305-296-1520Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/key-west-international-dance-company-presents-long-live-lambada

  • Nick Norman with Adam Wood

    Date(s): Apr 29, 2026Venue: Key West TheaterCategory: MusicPhone: 305-985-0433Website: https://thekeywesttheater.com/e/?event=1357832

  • Key West Songwriters Festival

    Date(s): Apr 29–May 3, 2026Venue: Festival / Key WestCategory: Festival / MusicWebsite: https://www.keywestsongwritersfestival.com/

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): Apr 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

    Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): Apr 30, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): May 1, 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

  • 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