7 events found.
Week of Events
Hot Girl Bummer at General Horseplay
Experience the electrifying performance of Hot Girl Bummer at General Horseplay, where vibrant live music meets inventive craft cocktails. Located in the lively heart of…
Free
Fancy Clown Art at Hinote at General Horseplay
Fancy Clown Art delivers an unforgettable performance at Hinote at General Horseplay, captivating audiences with their unique blend of artistry and entertainment. Their whimsical and…
Free
Monday, February 23, 2026
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February 23, 2026 -Tim Hollohan at Sloppy Joe’s Bar
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February 23, 2026 -Sunset Celebration at Mallory Square
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February 23, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan captivates audiences at Sloppy Joe's Bar, an iconic venue in Key West. Originally from Columbia, South Carolina, Tim graces the stage almost daily,…
Free
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
Tuesday, February 24, 2026
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February 24, 2026 -Ambitious Morning Runners
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February 24, 2026 -Sunset Celebration at Mallory Square
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February 24, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West for an invigorating start to your day. While there isn't a specific entertainer,…
Free
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
Wednesday, February 25, 2026
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February 25, 2026 -Mac Calhoun at The Bull & Whistle Bar
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February 25, 2026 -Sunset Celebration at Mallory Square
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February 25, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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February 25, 2026 -Kristen McNamara at The Bull & Whistle Bar
Mac Calhoun at The Bull & Whistle Bar
Mac Calhoun captivates audiences at The Bull & Whistle Bar with his dynamic musical performances. Nestled on Key West's vibrant Duval Street, this lively venue…
Free
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
Kristen McNamara at The Bull & Whistle Bar
Experience the enchanting performance of Kristen McNamara at The Bull & Whistle Bar. Known for her captivating voice and dynamic stage presence, Kristen enthralls audiences…
Free
Thursday, February 26, 2026
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February 26, 2026 -Ambitious Morning Runners
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February 26, 2026 -Sunset Celebration at Mallory Square
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February 26, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
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February 26, 2026New Normal at Sloppy Joe’s Bar
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West for an invigorating start to your day. While there isn't a specific entertainer,…
Free
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
New Normal at Sloppy Joe’s Bar
Catch New Normal live at Sloppy Joe's Bar from 10:00pm to 2:00am for an unforgettable night of music. Hailing from Bethlehem, PA, this band promises…
Free
Friday, February 27, 2026
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February 27, 2026 -Jessie Cotton Stone at The Bull & Whistle Bar
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February 27, 2026 -Sunset Celebration at Mallory Square
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February 27, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
Jessie Cotton Stone at The Bull & Whistle Bar
Experience the captivating performance of Jessie Cotton Stone at The Bull & Whistle Bar, a lively venue on Key West’s Duval Street. Known for his…
Free
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
Saturday, February 28, 2026
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February 28, 2026 -Sunset Celebration at Mallory Square
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February 28, 2026 -Caribe of Key West at El Meson de Pepes on Mallory Square
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…
Sunday, March 1, 2026
No events on this day.