Live Music Performances Across Key West’s Favorite Bars

Sunday, March 23, 2025, promises an incredible day filled with vibrant live music performances across Key West’s favorite bars and venues. Start the morning early at Two Friends Patio Restaurant & Bar with Alfonse playing from 8:30 AM to 11:30 AM. Fans of the legendary Sloppy Joe's Bar can enjoy Zack Seemiller kicking off at 10:00 AM, followed by Meghan Barter at noon, Mojito at 5:30 PM, and Radio Hero late-night at 10:00 PM.

At Irish Kevin's, the energy begins with Bradd Shadduck (11:00 AM - 2:30 PM), followed by Jeff Harris (2:30 PM - 6:00 PM), Oren Polak (6:00 PM - 10:00 PM), and closing with Mylo O'Maolain’s lively set (10:00 PM - 2:00 AM). Over at Schooner Wharf Bar & Grill, Big Daddy Rich keeps the vibe laid-back from 12:00 PM - 5:00 PM, while New Beginnings featuring Toko Irie brings reggae rhythms from 6:30 PM - 11:00 PM. Guests can also enjoy the entertaining Magic of Frank Everhart starting at 7:00 PM.

Live music enthusiasts shouldn't miss performances at Hog's Breath Saloon featuring Tim Hollohan (12:00 PM - 4:00 PM), the Dan Harvey Duo (4:30 PM - 8:30 PM), and Shelby Kemp Band at 9:00 PM. Hank's Hair of the Dog Saloon highlights Sid (1:00 PM - 4:00 PM), Jay (5:00 PM - 8:00 PM), and late-night entertainment by Cliff Cody (9:00 PM - 11:55 PM).

Other highlights around town include Gabriel Wright at Captain Tony's Saloon at 4:30 PM, Xperimento’s special Soundcheck Set at Green Parrot Bar at 5:30 PM, and the popular Tea Dance at La Te Da from 4:00 PM - 6:30 PM. Tipsy Rooster Liquor Store and Bar welcomes Tim Bradach (2:00 PM - 5:00 PM) and Andrew Gordan (8:00 PM - 11:00 PM), while Key West EmPOURium hosts Luke Berces (6:00 PM - 9:00 PM) and Karaoke fun from 8:00 PM - 12:30 AM. Laugh with comedian Tom Dustin performing at Comedy Key West at 8:30 PM.

Discover even more upcoming live music in Key West this week by visiting Key West Tourist’s Live Music Page.