Key West Event Calendar

Events

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  • Lobsterfest Lobster Boil

    The Porter Mansion Courtyard at Caroline's Cafe

    A Lobsterfest kickoff boil in a historic Old Town courtyard.

  • Hemingway in a Funny Way

    Weekly Friday comedy-history show. Date(s): Aug 7, 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

  • Key West Rum Fest

    Various Key West venues

    A week of rum tastings, music, sails, parties, and culinary pairings.

  • Key West Rum Fest

    Various Key West venues

    A week of rum tastings, music, sails, parties, and culinary pairings.

  • Key West Rum Fest

    Various Key West venues

    A week of rum tastings, music, sails, parties, and culinary pairings.

  • Key West Rum Fest

    Various Key West venues

    A week of rum tastings, music, sails, parties, and culinary pairings.

  • Key West Rum Fest

    Various Key West venues

    A week of rum tastings, music, sails, parties, and culinary pairings.

  • Key West Rum Fest

    A week of rum tastings, music, sails, parties, and culinary pairings.

  • Key West Rum Fest

    A week of rum tastings, music, sails, parties, and culinary pairings.

  • Rum Fest Key West

    Date(s): Aug 10–16, 2026Venue: Rum Fest Key WestCategory: Festival / SpiritsPhone: 910-599-6430Website: https://rumfestkeywest.com/

  • Tropical Heat

    Date(s): Aug 12–16, 2026Venue: Key West Business GuildCategory: Festival / LGBTQ+Phone: 305-294-4603Website: https://gaykeywestfl.com/tropical-heat/

  • Burgers & Buffet Tunes

    Weekly Thursday tribute lunch show. Date(s): Aug 13, 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

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