Live music in Key West, FL

Enjoy a free-entry bingo night at Key West Theater for ages 21 and over, featuring DJ Sanaris. Expect bingo with music, chances to win prizes and gift certificates, and the comfort of air conditioning. Bingo cards cost $5, and there is a two drink minimum. Attendees may bring friends and a lucky charm.

Enjoy a music trivia take on bingo built around themed playlists. As tracks play, name the song and the artist, and winners earn a spin of the Prize Wheel for prizes.

At 22&Co, Joe hosts a Thursday takeover that brings back the early 2000s. The night channels a 2001 vibe with high energy and playful nostalgia, turning the evening into a spirited throwback celebration.

An upbeat celebration of Motown and doo wop classics from the 1950s and 60s, this enduring revue has entertained Key West audiences for more than 43 years. Recognized as the island’s longest running musical show, The Fabulous Spectrelles perform energetic vocals and harmonies rooted in that golden era. The production is in residence at KAYA Key West EmPOURium, with performances presented in the venue’s Karaoke Lounge.

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.

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.