Alex Anthony Band at Hog’s Breath Saloon
Experience the dynamic energy of the Alex Anthony Band at Hog's Breath Saloon in Key West. Renowned for revolutionizing the modern cover band scene, Alex…
Free
40 events found.
Events for April 27, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Experience lively karaoke nights at Bobby's Monkey Bar, set in the heart of Key West's Old Town. With an engaging entertainer leading the fun, guests…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain captivates audiences at Irish Kevin's Bar with his energetic performances. Known for his engaging stage presence and musical talent, Mylo transforms the lively…
Free
The Audio Files at Sloppy Joe’s Bar
Experience The Audio Files at Sloppy Joe's Bar in Key West, where this innovative auditory ensemble captivates audiences with a rich tapestry of immersive soundscapes.…
Free
Yoga on the Beach – Ft Zachary Taylor
Experience serenity at Yoga on the Beach at Ft Zachary Taylor State Park in Key West. Enjoy sessions led by a renowned local yogi against…
$20
Aqua Yoga at Southernmost Beach Resort
Experience the serene practice of Aqua Yoga at Southernmost Beach Resort in Key West. Set amidst lush gardens and ocean views, this unique session is…
$20
Lance Taylor at Two Friends Patio Restaurant
Lance Taylor enchants audiences at Two Friends Patio Restaurant with his captivating performances. Set against the vibrant backdrop of Key West's Duval Street, his live…
Free
Rolando Rojas at Sloppy Joe’s Bar
Experience Rolando Rojas at Sloppy Joe's Bar, where his vibrant, dynamic musical style takes center stage. Known for his emotive performances and innovative approach, Rojas…
Free
Nick Norman at Rams Head Southernmost
Experience the soulful vocals and sharp songwriting of Nick Norman at Rams Head Southernmost. A South Carolina native now based in Key West, Nick delivers…
Free
Bradd Shadduck at Irish Kevin’s Bar
Experience the magnetic energy of Bradd Shadduck at Irish Kevin's Bar, nestled in Key West's vibrant Old Town. Known for engaging live performances, Shadduck enchants…
Free
Zack Seemiller at Hog’s Breath Saloon
At Hog's Breath Saloon, Zack Seemiller captivates audiences with his dynamic musical performances. A talented musician and songwriter, Zack combines his passion for music with…
Free
Tim Hollohan at Sloppy Joe’s Bar
At Sloppy Joe's Bar, Tim Hollohan captivates audiences with his dynamic musical performances. Known for his engaging presence and talent, Hollohan delivers an unforgettable live…
Free
Jay Klein at Schooner Wharf Bar
Jay Klein brings his multifaceted talent to the lively Schooner Wharf Bar in Key West. Known as a musician, entrepreneur, and tech enthusiast, his performances…
Free
Rick Fusco at Two Friends Patio Restaurant
Rick Fusco, a talented musician, captivates audiences at Two Friends Patio Restaurant in Key West. Known for his engaging performances, Fusco enchants diners with his…
Free
SUNSHINE Sandbar and Sunset
Experience an unforgettable day at SUNSHINE Sandbar and Sunset. Enjoy serene waters and picturesque views aboard Salty Bottom Boats. The highlight is a private concert…
Free
Jon Hollywood at Tiki House Key West
Experience the enigmatic Jon Hollywood at Tiki House Key West as he brings his charismatic presence and captivating storytelling to life. Known for blending humor…
Free
Jeff Harris at Irish Kevin’s Bar
At Irish Kevin's Bar, Jeff Harris delivers unforgettable performances that seamlessly blend music and comedy. Known for his engaging presence and heartfelt lyrics, he captivates…
Free
Cliff Cody at Mac’s Place
Join Texas-born, Key West-based indie country singer-songwriter Cliff Cody at Mac's Place for an unforgettable performance. Known for his powerful voice and heartfelt storytelling, Cody…
Free
Mike Stone Duo at Hog’s Breath Saloon
Experience the electrifying energy of the Mike Stone Duo at Hog's Breath Saloon. Led by the talented Mike Stone, this dynamic musical group captivates audiences…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling performances of the World Famous 801 Girls at their 5pm show in Key West's 801 Bourbon Bar. These talented drag queens captivate…
Glow Hours on Hugh’s View
Experience Glow Hours on Hugh's View at The Studios of Key West, where captivating entertainers light up this iconic art center. Enjoy live performances amidst…
Tony Roberts at Rams Head Southernmost
Experience the charismatic Tony Roberts at Rams Head Southernmost. Renowned for his work in Woody Allen films like Annie Hall, Tony blends his versatile talents…
Free
Sunset Celebration at Mallory Square
Experience the Sunset Celebration at Mallory Square, where the star attraction is the talented street performers. From the mesmerizing jugglers to the well-known cat man,…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant rhythms of Caribe of Key West at El Meson de Pepes on Mallory Square. This family-owned gem enchants guests with its lively…
CW Colt at Two Friends Patio Restaurant
Experience the captivating performance of CW Colt at Two Friends Patio Restaurant. A seasoned musician, CW Colt brings his unique sound to this vibrant Key…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Experience the dynamic energy of Pete & Larry's Sloppy 2nds at Sloppy Joe's Bar, a historic Key West venue. Known for their eclectic and humorous…
Free
Barrett Thomas at The Alamo Key West
Barrett Thomas, a dynamic live musician and talented looper, captivates audiences at The Alamo Key West with his innovative performances. Based in Key West, his…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin's Bar in Key West, Florida. Known for his captivating and vibrant performances, he seamlessly blends music…
Free
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
Charity Bingo at The Green Parrot
Join us for an unforgettable night at Charity Bingo at The Green Parrot in Key West. Experience the vibrant atmosphere of this historic dive bar,…
Free
Magic The Gathering Night at The Retro Room
Immerse yourself in the nostalgic ambiance of The Retro Room during Magic The Gathering Night. Enjoy craft beers and a lively atmosphere as you engage…
Free
Lary Smith Jazz Jam at William Weech American Legion Post 168
Join the captivating jazz night at William Weech American Legion Post 168, Key West, featuring the remarkable musician Larry Smith. Experience his dynamic and soulful…
Free
Joe The Show at Schooner Wharf Bar
Experience the extraordinary talent of Joe The Show at Schooner Wharf Bar. Known for his tireless dedication and dynamic energy, JTS captivates audiences daily in…
Free
Elle Haley at Halo Rooftop Lounge Bar at The Saint
Experience the soulful tunes of Elle Haley, a vibrant musician from the Florida Keys, at Halo Rooftop Lounge Bar. Her captivating performances transform evenings into…
Free
Gregory James at La Te Da
Gregory James, a versatile entertainer and musician known for his talent in acting, modeling, and performing arts, captivates audiences at La Te Da. With skills…
Free
Kari Wolf at Tiki House Key West
Kari Wolf, a dynamic musician from Key West, captivates audiences with her soulful melodies and unique style at Tiki House Key West. Known for her…
Free
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