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
Sunday, April 19, 2026
Alfonse at Two Friends Patio Restaurant & Bar
April 19, 2026 - 8:30 a.m. - 11:30 a.m.
Two Friends Patio Restaurant & Bar - 512 Front St, Key West, FL 33040
Chris Thomas at Sloppy Joe's Bar
April 19, 2026 - 10 a.m.
Sloppy Joe's Bar - 201 Duval St, Key West, FL 33040
Bradd Shadduck at Irish Kevin's
April 19, 2026 - 11 a.m. - 2:30 p.m.
Irish Kevin's - 211 Duval St, Key West, FL 33040
Andy Westcott at Sloppy Joe's Bar
April 19, 2026 - noon
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.
Erica "Sunshine" Lee at Sunset Pier
April 19, 2026 - 1 p.m. - 4 p.m.
Sunset Pier - 0 Duval St, Key West, FL 33040
Mike Emerson Jazz Quartet at 1:00 & 3:00 at Green Parrot Bar
April 19, 2026 - 1 p.m.
Green Parrot Bar - 601 Whitehead St, Key West, FL 33040
Jeff Harris at Irish Kevin's
April 19, 2026 - 2:30 p.m. - 6 p.m.
Irish Kevin's - 211 Duval St, Key West, FL 33040
Dead Fest Key West at Alamo Key West
April 19, 2026 - 4 p.m. - 7 p.m.
Alamo Key West - 4 Charles St, Key West, FL 33040
Happy Dog at Alamo Key West
April 19, 2026 - 4 p.m. - 7 p.m.
Alamo Key West - 4 Charles St, Key West, FL 33040
TEA DANCE! at La Te Da
April 19, 2026 - 4 p.m. - 6:30 p.m.
La Te Da - 1125 Duval St, Key West, FL 33040
Larry Smith at Tavern N Town
April 19, 2026 - 5 p.m. - 6 p.m.
Tavern N Town - 3841 N. Roosevelt Blvd, Key West, FL 33040
Larry Smith has built an extraordinary career in music, excelling in performance, songwriting, and production. A Pennsylvania native, Larry began playing piano at age four and professionally performed on clarinet by 12. Rising to national prominence with Don Kirshner, he later co-wrote and arranged critically acclaimed tracks for The Allen Harris Band under Columbias Tappan Zee label, collaborating with legends like Michael Brecker and Hubert Laws. Now based in Key West for over 20 years, Larry produces the renowned Larry Smith Sunday Showcase Series, featuring top talent from across the globe. He continues to compose, perform, and record with passion.
The Shanty Hounds at Two Friends Patio Restaurant & Bar
April 19, 2026 - 5 p.m. - 9 p.m.
Two Friends Patio Restaurant & Bar - 512 Front St, Key West, FL 33040
The Shanty Hounds are a dynamic duo featuring singer-songwriters Dani Hoy and Key West Chris Rehm. Renowned for their captivating performances, they expertly blend unique covers and original songs, spanning Americana classics from artists like Fleetwood Mac, Johnny Cash, Tom Petty, and more. Dani's magnetic voice draws crowds, while Chris's guitar mastery keeps them enthralled. With years of professional experience, they've been delighting audiences worldwide since 2013. Catch their high-energy shows weekly at Two Friends Patio Restaurant or Rick's Bar in Key West, where they bring an unforgettable mix of talent, passion, and entertainment to every performance.