Live Entertainment
Nightlife in Key West
Discover live music in Key West, the ultimate destination for unforgettable entertainment and nightlife! Our Key West live music calendar showcases today's hottest performances at vibrant bars and outdoor venues both on and off Duval Street. Experience island rhythms at all hours—sing along, dance under the stars, or unwind with your favorite local bands. Check out the complete Key West music schedule and immerse yourself in the lively atmosphere of this renowned live entertainment hotspot. Don’t miss tonight’s shows and events; join the party and feel the beat of paradise in Key West! View Entertainment Schedule by Venue
Wednesday, March 19, 2025
Big Daddy Rich at Dante's Key West Pool Bar and Restaurant
March 19, 2025 - 4:30 p.m. - 7:30 p.m.
Dante's Key West Pool Bar and Restaurant - 951 Caroline St, Key West, FL 33040
Big Daddy Rich is a premier live musician based in Key West, delivering unforgettable performances for bar gigs, clubs, weddings, parties, and corporate events. With unmatched musical talent, versatility, and charm, he customizes every show, from intimate dinners to high-energy dance floors. Book Big Daddy Rich for an exceptional musical experience!
Dan Harvey Duo at Hog's Breath Saloon
March 19, 2025 - 4:30 p.m. - 8:30 p.m.
Hog's Breath Saloon - 400 Front St, Key West, FL 33040
Mike Emerson at Tavern N Town
March 19, 2025 - 5 p.m. - 9 p.m.
Tavern N Town - 3841 N. Roosevelt Blvd, Key West, FL 33040
Victoria Lee at Hank's Hair of the Dog Saloon
March 19, 2025 - 5 p.m. - 8 p.m.
Hank's Hair of the Dog Saloon - 409 Caroline St, Key West, FL 33040
Andy Westcott Band at Sloppy Joe's Bar
March 19, 2025 - 5:30 p.m.
Sloppy Joe's Bar - 201 Duval St, Key West, FL 33040
The Andy Westcott Band, a Key West powerhouse, blends timeless Southern rock with funk, twang, and soul. Influenced by legends and modern icons alike, their dynamic live shows at iconic venues like The Green Parrot captivate audiences. Anticipate fresh tunes from their upcoming second album.
Isaac Eady & Third Moon at 5:30, 9:00 & 11:00 at Green Parrot Bar
March 19, 2025 - 5:30 p.m.
Green Parrot Bar - 601 Whitehead St, Key West, FL 33040
Irish Kevin at Irish Kevin's
March 19, 2025 - 6 p.m. - 10 p.m.
Irish Kevin's - 211 Duval St, Key West, FL 33040
Kenny P - Family Night at Boondocks Grille
March 19, 2025 - 6 p.m. - 9 p.m.
Boondocks Grille - 27205 Overseas Hwy, Ramrod Key, FL 33042
Gary Hempsey at Alamo Key West
March 19, 2025 - 6:30 p.m.
Alamo Key West - 4 Charles St, Key West, FL 33040
Gary Hempsey, a renowned Key West musician, captivates audiences with his dynamic performances blending adult acoustic alternative and influences from countless artists. Playing 280 shows annually across North America, Gary's repertoire spans originals and beloved covers, including songs from his acclaimed 2020 album Don't Forget Where You Come From. As a rhythm guitarist and vocalist with The Happy Dog and That Hippie Band, Gary's energy shines in every performance. With over 25 years of experience, including opening for Kenny Chesney, Gary remains a Key West favorite, delivering unforgettable music at iconic venues like Schooner Wharf and Green Parrot.
Live Jazz combo at ViV Wine Bistro
March 19, 2025 - 6:30 p.m. - 9:30 p.m.
ViV Wine Bistro - 300 Petronia St, Key West, FL 33040
Raven Cooper at Schooner Wharf Bar & Grill
March 19, 2025 - 6:30 p.m. - 11 p.m.
Schooner Wharf Bar & Grill - 202 William St, Key West, FL 33040
Raven Cooper is a celebrated Key West musician, captivating audiences with her eclectic mix of jazz, rock, pop, and country favorites. Known for her soulful vocals reminiscent of Janis Joplin and Billie Holiday, she combines powerful guitar skills with dynamic audience interaction. A staple at Schooner Wharf Bar for over 15 years, Ravens performances are a vibrant experience, blending spontaneity and heart. Her album South of North features original Key West songs, and she continues to promote women in music while delighting crowds with her extensive repertoire of 650+ songs. Catch her live for an unforgettable musical journey!
Kim Jade at Mac's Place
March 19, 2025 - 7 p.m. - 10 p.m.
Mac's Place - 1605 N Roosevelt Blvd, Key West, FL 33040