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, October 14, 2026
Alfonse at Two Friends Patio Restaurant & Bar
Oct. 14, 2026 - 9:30 a.m. - 12:30 p.m.
Two Friends Patio Restaurant & Bar - 512 Front St, Key West, FL 33040
Kaira Jayde at Sloppy Joe's Bar
Oct. 14, 2026 - 10 a.m.
Sloppy Joe's Bar - 201 Duval St, Key West, FL 33040
Oren Polak at Irish Kevin's
Oct. 14, 2026 - 11 a.m. - 2:30 p.m.
Irish Kevin's - 211 Duval St, Key West, FL 33040
Brian Roberts at Sloppy Joe's Bar
Oct. 14, 2026 - noon
Sloppy Joe's Bar - 201 Duval St, Key West, FL 33040
Brian Roberts is a dynamic musician based in the Florida Keys, blending acoustic and island-rock styles. Starting his journey at 12, he excelled in music, earning the Louis Armstrong Jazz Award in high school. Transitioning from chef to full-time musician, he founded The Prime Movers and delivers over 300 performances annually, including regular sets at Sloppy Joes in Key West. His albums, At The Time and Christmas Music, showcase heartfelt originals and tributes to musical idols. As the owner of Semi Tropical Music, Inc., Brian offers unforgettable entertainment for weddings, events, and clubs, embodying the vibrant spirit of island life.
Jonathan Williams at Pier House Resort & Spa
Oct. 14, 2026 - noon - 3 p.m.
Pier House Resort & Spa - One Duval St, Key West, FL 33040
Philadelphia native Jonathan Williams, a versatile musician with nearly 15 years of experience, excels in delivering iconic hits spanning five decades. Based in Key West, he has performed over 400 shows at his peak, enchanting audiences at top venues, weddings, and private events across the Florida Keys and South Florida.
Tony Baltimore at Schooner Wharf Bar & Grill
Oct. 14, 2026 - noon - 5 p.m.
Schooner Wharf Bar & Grill - 202 William St, Key West, FL 33040
Tony Baltimore, a dynamic singer/songwriter and multi-instrumentalist raised in Maryland, blends alternative roots-rock with influences from New Orleans, Brit-pop, and gospel. A Key West icon, Tonys musical journey began with drums at age four, evolving into a vibrant career shaped by legends like The Beatles and Queen. After earning his MFA in poetry, he found creative inspiration in Key Wests unique music scene, releasing acclaimed albums like Define the Blur and Hear Me In. His latest work, Lets All Go Insane, showcases hook-driven, genre-bending tracks. Known for electrifying performances, Tony continues to captivate audiences with heartfelt storytelling and bold creativity.
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Oct. 14, 2026 - 12:30 p.m.
Comedy Key West - 218 Whitehead St, Unit 5, Key West, FL 33040
Shastina Chiles at Hank's Hair of the Dog Saloon
Oct. 14, 2026 - 1 p.m. - 4 p.m.
Hank's Hair of the Dog Saloon - 409 Caroline St, Key West, FL 33040
Shastina Chiles, a gifted songwriter and performer, captivates audiences with her distinctive blend of Pop and R&B. Based in Key West, she delivers powerful, guitar-driven performances at top venues and live streams for her growing fan base nationwide. Shastina has shared stages with icons like Phil Vassar, Molly Hatchet, and Jimmy Buffett, offering both popular covers and soulful original songs.
Jeff Harris at Irish Kevin's
Oct. 14, 2026 - 2:30 p.m. - 6 p.m.
Irish Kevin's - 211 Duval St, Key West, FL 33040
Harley Ray at Rick's Bar Key West
Oct. 14, 2026 - 3 p.m. - 7 p.m.
Rick's Bar Key West - 202-208 Duval Street, Key West, FL 33040
Jonathan Williams at Two Friends Patio Restaurant & Bar
Oct. 14, 2026 - 3 p.m. - 6 p.m.
Two Friends Patio Restaurant & Bar - 512 Front St, Key West, FL 33040
Philadelphia native Jonathan Williams, a versatile musician with nearly 15 years of experience, excels in delivering iconic hits spanning five decades. Based in Key West, he has performed over 400 shows at his peak, enchanting audiences at top venues, weddings, and private events across the Florida Keys and South Florida.
Just George at Old Sailor Bar
Oct. 14, 2026 - 3 p.m. - 7 p.m.
Old Sailor Bar - 430 Greene St, Key West, FL 33040