This weekend in Key West, FL

● Listings verifiedMonday, September 21 · every listing checked against its source by our Key West editors

Saturday & Sunday, Sep 26–27

7 events, 3 free. All of this week's events →

Saturday, September 26 3 events
  • 7pm

    Full Moon Magic Ghost Stories

    Dewey Deck at Southernmost Beach Resort, 1319 Duval St, Key West · verified Sep 20
    Free

    On the Dewey Deck, hear dark and haunted stories drawn from Key West history. This free program is open to all ages. Space is limited, and reservations are required. To reserve a spot, text "Save Me A Seat" to 717.816.4153.

    Event website ↗
  • 7pm

    Of Course Dave

    The Retro Room, 126 Simonton St, Key West · verified Sep 18
    See details

    Saturday nights get a boost with live DJ sets from Of Course Dave. Enjoy themed tracks blended throughout the evening for a lively, party-ready soundtrack.

    Event website ↗
  • 7pm

    Full Moon Ghost Show

    Dewey Deck at Southernmost Beach Resort, 1319 Duval St, Key West · verified Sep 18
    Free

    On the Dewey Deck, storytellers share dark, haunted tales from Key West’s past. The event is free and open to all ages. Reservations are required because space is limited; to hold a spot, text the words Save Me A Seat to 717-816-4153.

    Event website ↗
Sunday, September 27 4 events
  • 11am

    Sunday Funday

    S/V Argo Navis, 0 Duval Street, Key West · verified Sep 18
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    Make the most of a summer Sunday on the water in Key West with a laid-back sail, time to swim in clear, warm waters, and plenty of tasty bites and cool beverages to enjoy along the way. Pricing is $135 for adults and $99 for children under 12.

    Event website ↗
  • 12pm

    Kenny

    Geiger Key Marina and Fish Camp, 5 Geiger Rd, Key West · verified Sep 18
    See details

    LANDFALL’s Kenny Yarbrough brings a solo performance to Geiger Key Marina and Fish Camp in Key West, blending Jimmy Buffett favorites, tropical classics, classic rock, country, singer songwriter hits, and a few surprises. The music pairs with a waterfront setting framed by mangroves and working boats, where Old Florida character, relaxed vibes, and fresh seafood set the tone. Popular with boaters, anglers, and paddlers, this hideaway is known for peaceful views and memorable sunsets. Guests can enjoy fresh seafood, unwind by the water, and take in a laid back Keys soundtrack in a place locals treasure and visitors remember.

    Event website ↗
  • 1pm

    Farm Open House

    Monroe County Sheriff's Office Animal Farm, Key West
    Free

    Monroe County Sheriff's Office Animal Farm welcomes visitors for an open house. Admission is free, and donations are appreciated.

    Event website ↗
  • 7pm

    80s & 90s Trivia Night

    The Retro Room, 126 Simonton St, Key West · verified Sep 18
    See details

    Live team trivia at the Retro Room spotlights 80s and 90s pop culture. Teams of up to six players compete for prizes, creating a lighthearted throwback challenge for fans of the era.

    Event website ↗

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