Martini Monday at Virgilios
Experience the captivating sounds of talented musicians at Martini Monday at Virgilio's in Old Town Key West. This stylish cocktail lounge offers an impressive martini…
Free
43 events found.
Events for April 28, 2026
Ongoing
Shelby Kemp Band at Hog’s Breath Saloon
The Shelby Kemp Band delivers an electrifying fusion of rock, blues, and soul at Hog's Breath Saloon. Frontman Shelby Kemp leads with dynamic vocals and…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant atmosphere at Bobby's Monkey Bar for an unforgettable karaoke night. The entertainer takes center stage, captivating the crowd with charisma and energy,…
Mylo O’Maolain at Irish Kevin’s Bar
At Irish Kevin’s Bar in Key West, Mylo O’Maolain captivates audiences with his dynamic performances and engaging charm. Known for his energetic style and musical…
Free
The Audio Files at Sloppy Joe’s Bar
The Audio Files bring an immersive auditory experience to Sloppy Joe's Bar, creating a vibrant atmosphere in historic Key West. This dynamic platform captivates audiences…
Free
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West, a stunning oceanfront location famous for its breathtaking sunset views and peaceful ambiance.…
Free
Yoga on the Beach – Ft Zachary Taylor
Join Yoga on the Beach at Fort Zachary Taylor State Park for a rejuvenating session that combines tranquility with stunning views. This event offers a…
$20
Jonathan Williams at Two Friends Patio Restaurant
Jonathan Williams captivates audiences at Two Friends Patio Restaurant with his engaging live performances. Known for his musical versatility, he creates an unforgettable atmosphere in…
Free
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, an enriching experience set against the serene backdrop of the Key West Tropical Forest & Botanical Garden.…
$20
Zack Seemiller at Sloppy Joe’s Bar
Zack Seemiller captivates audiences at Sloppy Joe's Bar with his dynamic performances, blending his talents as a musician and songwriter. Known for his engaging presence,…
Free
Ross Brown at Rams Head Southernmost
Ross Brown, a versatile musician from Key West, FL, captivates audiences with his dynamic performances at Rams Head Southernmost. Known for his adventurous spirit and…
Free
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings vibrant energy to Irish Kevin's Bar, captivating audiences with his dynamic performances. As a talented musician, he enhances the lively atmosphere of…
Free
Caleb Tyler at Tiki House Key West
Experience the dynamic performance of Caleb Tyler at Tiki House Key West, where he captivates audiences with his engaging music in the heart of Old…
Free
Harley Ray at Hog’s Breath Saloon
Harley Ray captivates audiences at Hog's Breath Saloon with his passionate and innovative songwriting. Known for melodies that resonate personally, Ray's music exudes authenticity and…
Free
Ross Brown at Sloppy Joe’s Bar
Ross Brown, a charismatic musician, captivates audiences at Sloppy Joe's Bar with his eclectic performances. Embracing his title as a Spiritual Gangster, Brown infuses his…
Free
Oren Polak at Schooner Wharf Bar
Oren Polak, a versatile musician and band leader, enchants audiences at Schooner Wharf Bar with his unique sound and captivating performances. Known for his mission…
Free
Kitty at Two Friends Patio Restaurant
Experience the enchanting performance of musician Kitty Steadman at Two Friends Patio Restaurant. As a Key West favorite since 1967, the venue provides a vibrant…
Free
Industry Night at The Retro Room
Industry Night at The Retro Room features an exceptional entertainer that sets the stage for an unforgettable evening. Nestled in Old Town Key West, this…
Free
Joe The Show at Tiki House Key West
Experience the dynamic talent of Joe The Show at Tiki House Key West. Known for his tireless dedication and passion, JTS captivates audiences daily with…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin, a charismatic and humorous performer, brings infectious energy to Irish Kevin's Bar in Key West. With his genuine charm and captivating presence, he…
Free
Juno Smile at Mac’s Place
Experience the enchanting melodies of Juno Smile at Mac's Place. This captivating duo brings a harmonious fusion of folk and acoustic rock to the vibrant…
Free
Mike Stone Duo at Hog’s Breath Saloon
Experience the captivating energy of the Mike Stone Duo at Hog's Breath Saloon. Led by the talented musician Mike Stone, the duo delivers dynamic performances…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling charisma of the World Famous 801 Girls at their 5pm show. These talented drag queens captivate audiences with their vibrant performances at…
Glow Hours on Hugh’s View
Join us at Glow Hours on Hugh's View for an unforgettable night atop The Studios of Key West. Experience captivating performances by talented local artists,…
Elle Haley with Lexi Lew at Hank’s Hair of the Dog Saloon
Elle Haley, a dynamic musician from the Florida Keys, brings her soulful tunes to life at Hank's Hair of the Dog Saloon. Known for her…
Free
Zack Seemiller at Rams Head Southernmost
Experience the captivating performance of Zack Seemiller at Rams Head Southernmost. An accomplished musician and songwriter, Zack combines his passion for personal development with his…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant atmosphere at El Meson de Pepes on Mallory Square, where Caribe of Key West brings lively performances that captivate audiences. Savor authentic…
Sunset Celebration at Mallory Square
Experience the Sunset Celebration at Mallory Square, where the captivating entertainer, the famous cat man, mesmerizes audiences with his unique feline performances. As the sun…
Free
Ericson Holt at Two Friends Patio Restaurant
Experience the captivating performance of Ericson Holt at Two Friends Patio Restaurant. Known for his soulful tunes and dynamic stage presence, Ericson enchants audiences with…
Free
Jerico Duo at Sloppy Joe’s Bar
Experience the electrifying sounds of Jerico Rockabilly Duo at Sloppy Joe's Bar, where their dynamic rock 'n' roll performances captivate audiences. This talented duo revives…
Free
Bo Fodor at RockHouse Live Key West
At RockHouse Live Key West, Bo Fodor captivates audiences with his innovative artistic approach. Known for his storytelling and visual expression, Bo blends traditional techniques…
Free
Happy Dog at The Alamo Key West
Experience the electrifying energy of the Happy Dog Band at The Alamo Key West. This improvisational jam band channels the psychedelic era with dynamic live…
Free
NY Pauly at Irish Kevin’s Bar
Experience the legendary NY Pauly at Irish Kevin’s Bar in Key West. A captivating performer, NY Pauly seamlessly blends music and entertainment, making every show…
Free
Gary Hempsey at Schooner Wharf Bar
Experience the captivating performances of Gary Hempsey at Schooner Wharf Bar, an iconic waterfront venue in Key West. Known for his engaging musical talent, Gary…
Free
Comedy Key West Open Mic at Comedy Key West
Join Comedy Key West's Open Mic Night for an evening bursting with laughter and creativity. This vibrant event welcomes budding comedians and seasoned performers alike…
Free
Jack Wolf at Halo Rooftop Lounge Bar at The Saint
Experience the soulful performances of Jack Wolf at the Halo Rooftop Lounge Bar at The Saint Hotel. Based in Key West, this talented singer-songwriter enchants…
Free
Ronnie & Gregory at La Te Da
Ronnie and Gregory captivate audiences at La Te Da with their vibrant personalities and dynamic performances. Their synergy blends creativity and practicality, creating engaging entertainment…
Free
Aaron Hudgins at Tiki House Key West
Aaron Hudgins captivates the crowd at Tiki House Key West with his exceptional musical talent. As a seasoned musician, his performances blend seamlessly with the…
Free
Randy Roberts at La Te Da
Randy Roberts dazzles audiences at La Te Da with his electrifying live performances, showcasing over three decades of talent. Renowned for his authentic vocals, Roberts…
$35
Shelby Kemp Band at Hog’s Breath Saloon
The Shelby Kemp Band delivers an electrifying performance at Hog's Breath Saloon, captivating audiences with their dynamic fusion of rock, blues, and soul. Frontman Shelby…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant atmosphere at Bobby's Monkey Bar in Key West for an unforgettable evening of karaoke. Enjoy captivating performances by talented entertainers as they…
Simonian Wolf at Irish Kevin’s Bar
Simonian Wolf captivates audiences at Irish Kevin's Bar with their charismatic presence and innovative performances. Known for their unique blend of talents, they inspire and…
Free
The Audio Files at Sloppy Joe’s Bar
The Audio Files captivate audiences at Sloppy Joe's Bar with their innovative and dynamic auditory experiences. They blend storytelling, interviews, and meditative music into an…
Free