Joe The Show at Sloppy Joe's Bar
2026-01-19 10:00 - 11:45 (America/New_York)
Experience the captivating performance of Joe The Show at Sloppy Joe’s Bar, a historic Key West landmark. Known for his dynamic musical talent, Joe The Show brings electrifying energy to the lively atmosphere. Enjoy his sensational entertainment while savoring delicious American fare and drinks in this iconic venue on Duval Street.

Webb Dillard ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-19 12:00 - 15:00
Experience the captivating sounds of Webb Dillard at Rick’s Bar, nestled within the vibrant Rick’s Entertainment Complex in Old Town Key West. Known for his soulful musical talent, Webb Dillard electrifies the crowd, creating an unforgettable live music experience. Immerse yourself in a night of rhythm and entertainment at Key West’s largest club.

Tim Hollohan at Sloppy Joe's Bar
2026-01-19 12:00 - 16:45
Tim Hollohan, a talented musician from Columbia, South Carolina, graces the stage almost daily at Key West’s legendary Sloppy Joe’s Bar. Known for his captivating presence and engaging performances, Tim enriches the bar’s lively atmosphere, making it a must-visit destination for music enthusiasts and visitors alike.

Jay Klein at Schooner Wharf Bar
2026-01-19 12:00 - 17:00
Jay Klein captivates audiences at the Schooner Wharf Bar, infusing the open-air venue with his vibrant musical talent. As a local favorite, his performances resonate with the laid-back, island vibe of Key West. Guests can enjoy his engaging live music while soaking in the waterfront views and savoring fresh seafood delights.

Just George ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-19 15:00 - 19:00
Experience an unforgettable night with Just George at Rick’s Bar, located within the vibrant Rick’s Entertainment Complex in Old Town Key West. As you enjoy his captivating live music performance, immerse yourself in the lively atmosphere of Key West’s largest club, featuring eight famous bars and an electric nightlife.

Joe The Show at Schooner Wharf Bar
2026-01-19 18:30 - 22:30
Experience the captivating performance of Joe The Show at Schooner Wharf Bar, where this dynamic musician brings vibrant energy to Key West’s iconic waterfront venue. Enjoy his eclectic live music in a laid-back, open-air setting with dockside views. Savor fresh seafood and island cuisine for an unforgettable evening of entertainment.

Aaron Hudgins ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-19 20:00 - 23:59
Experience the captivating performance of musician Aaron Hudgins at Rick’s Bar, located in the vibrant Rick’s Entertainment Complex in Old Town Key West. Known for his dynamic energy, Hudgins delivers unforgettable live music that keeps audiences engaged. With eight bars and endless nightlife, Rick’s promises an exhilarating evening filled with music and fun.

Brian Roberts at Sloppy Joe's Bar
2026-01-20 12:00 - 16:45
Brian Roberts captivates audiences at Sloppy Joe’s Bar with his dynamic musical performances. As a staple of the Key West live music scene, Roberts delivers engaging sets that resonate with both locals and tourists. His presence at the historic venue, known for its vibrant atmosphere, ensures an unforgettable entertainment experience on Duval Street.

Jesse Lee ~Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-20 15:00 - 19:00
Experience the captivating sounds of Jesse Lee Jr at Rick’s Bar, nestled within Key West’s bustling Rick’s Entertainment Complex. Known for his engaging performances and musical prowess, Jesse Lee brings an electrifying energy to this vibrant nightlife hotspot, promising an unforgettable evening filled with live music and lively entertainment.

Gary Hempsey at Schooner Wharf Bar
2026-01-20 18:30 - 22:30
Experience the soulful sounds of Gary Hempsey at Schooner Wharf Bar, Key West’s beloved waterfront venue. Known for his magnetic stage presence and captivating performances, Gary brings a unique blend of melodies that resonate with the laid-back island vibe. Enjoy live music in an open-air setting with stunning dockside views.

Charles Miller ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-20 19:00 - 23:00
Experience the captivating sounds of musician Charles Miller at Rick’s Bar, located downstairs at Rick’s Entertainment Complex in Key West. Known for his engaging performances, Charles Miller energizes the vibrant nightlife scene with his soulful melodies, making every evening unforgettable. Enjoy a mix of live music, diverse drinks, and lively ambiance.

Izzy Zaidman at Sloppy Joe's Bar
2026-01-21 10:00 - 11:45
Izzy Zaidman, a talented musician and Key West transplant, captivates audiences at Sloppy Joe’s Bar with the soulful sounds of his Steel Resonator guitar. Embracing the spirit of American Roots music, Izzy transforms the historic haunt into a vibrant musical oasis, showcasing his artistry amidst the lively Duval Street scene.

Brian Roberts at Sloppy Joe's Bar
2026-01-21 12:00 - 16:45
Brian Roberts captivates audiences at Sloppy Joe’s Bar with his dynamic live performances, contributing to the vibrant Key West music scene. His compelling musicianship resonates through the historic venue, offering a memorable experience. Sloppy Joe’s, a beloved landmark on Duval Street, perfectly complements Roberts’s engaging music with its lively atmosphere and rich history.

Tony Baltimore at Schooner Wharf Bar
2026-01-21 12:00 - 17:00
Tony Baltimore brings his vibrant musical talent to the Schooner Wharf Bar, infusing the historic Key West venue with his captivating performances. Against the backdrop of stunning dockside views, he enchants audiences with his dynamic sound, creating an unforgettable experience. Join Tony for an evening of live music, island vibes, and pure entertainment bliss.

Harley Ray ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-21 15:00 - 19:00
Harley Ray captivates audiences at Rick’s Bar, located in Key West’s vibrant Entertainment Complex. A talented musician, Ray electrifies the stage with his dynamic performances. Guests can enjoy a night of unforgettable live music, surrounded by the lively atmosphere of bars, dancing, and unmatched nightlife. An essential stop for music lovers in Old Town.

Jeff Clark at Schooner Wharf Bar
2026-01-21 18:30 - 22:30
Jeff Clark, a talented musician, captivates audiences at the Schooner Wharf Bar with his exceptional performances. Known for his engaging style, Jeff brings a vibrant energy to this open-air waterfront venue in Key West. His music complements the laid-back atmosphere, enhancing the bar’s reputation as a local favorite for live entertainment.

Ben Harrison at Key West Theater
2026-01-21 19:00 - 21:00
Experience the dynamic performance of musician Ben Harrison at the Key West Theater’s Backstage Listening Room. Known for his captivating stage presence and soulful melodies, Harrison delivers an intimate acoustic set in this historic venue. Join an evening filled with artistry and charm in the heart of Old Town Key West.

Joe the Show ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-21 19:00 - 23:00
Experience the unforgettable performance of Joe the Show at Rick’s Bar, nestled in Old Town Key West’s bustling Rick’s Entertainment Complex. Renowned for his captivating musical talent, Joe energizes the crowd with his electrifying performances. Join Joe for an evening of extraordinary live music, laughter, and excitement at this vibrant nightlife hotspot.

Victoria Leigh at Sloppy Joe's Bar
2026-01-22 10:00 - 11:45
Victoria Leigh, a dynamic Florida Keys-based artist, captivates audiences at Sloppy Joe’s Bar with her high-energy shows. Known for her skillful fusion of reggae, pop, and rock, she performs over 350 gigs annually, utilizing live looping and creative mashups to deliver unforgettable musical experiences in this historic Key West venue.

Jeff Clark at Sloppy Joe's Bar
2026-01-22 12:00 - 16:45
Jeff Clark electrifies Sloppy Joe’s Bar with his captivating performances, filling the historic Key West landmark with spirited energy. Renowned for his dynamic music, Clark transforms the lively venue on Duval Street into an unforgettable experience. Patrons savor delicious American fare and cocktails while enjoying Clark’s exceptional talent in this iconic setting.

Ross Brown at Schooner Wharf Bar
2026-01-22 12:00 - 17:00
Ross Brown, a captivating musician, brings his dynamic talent to the stage at Schooner Wharf Bar. Known for his engaging performances, Ross creates an unforgettable experience in the laid-back, open-air venue. Set against the stunning backdrop of Key West’s Seaport, his music is a perfect addition to this local favorite’s vibrant atmosphere.

Jeff Harris ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-22 15:00 - 19:00
Experience the captivating performance of Jeff Harris at Rick’s Bar, nestled within Rick’s Entertainment Complex in Old Town Key West. Renowned for his musical prowess, Jeff Harris fills the venue with mesmerizing tunes amidst the vibrant nightlife. This dynamic musician ensures an unforgettable evening of live music in the heart of Key West.

Waynard Scheller at Schooner Wharf Bar
2026-01-22 18:30 - 22:30
Waynard Scheller captivates audiences at the Schooner Wharf Bar with his dynamic musical performances. Known for his engaging presence, Scheller infuses vibrant energy into the historic Key West venue. This open-air bar, famous for its stunning dockside views and laid-back atmosphere, serves as the perfect backdrop to Scheller’s unforgettable live music.

Andrew B. ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-22 19:00 - 23:00
Experience the captivating sounds of Andrew B., a talented musician known for his engaging performances, at Rick’s Bar in Key West’s largest entertainment complex. Nestled in vibrant Old Town, Rick’s offers an unforgettable nightlife experience with live music. Join Andrew B. for an evening of musical brilliance in a lively, iconic setting.

Wynn Tayor ~ Rick's Bar Downstairs Stage at Rick's Entertainment Complex
2026-01-23 12:00 - 16:00
Experience the captivating performance of Wynn Taylor on the Downstairs Stage at Rick’s Bar within Rick’s Entertainment Complex. Renowned for his exceptional musical talent, Wynn Taylor delivers an unforgettable live music experience. Nestled in the vibrant heart of Old Town Key West, this lively venue promises an exhilarating evening of entertainment and nightlife.

Tim Hollohan at Sloppy Joe's Bar
2026-01-23 12:00 - 16:45
Experience the vibrant energy of Tim Hollohan at Sloppy Joe’s Bar, a historic Key West venue. Originally from Columbia, South Carolina, Tim captivates audiences with his engaging stage presence and dynamic performances. Enjoy great music and drinks in an iconic setting, perfect for people-watching and savoring true Old Town charm.

Tony Baltimore at Schooner Wharf Bar
2026-01-23 12:00 - 17:00
Experience the captivating sounds of musician Tony Baltimore at the iconic Schooner Wharf Bar in Key West. With stunning dockside views and a laid-back atmosphere, Tony’s live performances are a must-see, blending local charm with soulful melodies. Enjoy his music alongside fresh seafood and two daily happy hours for an unforgettable evening.

Joe the Show ~ Rick's Bar Downstairs Stage at Rick's Entertainment Complex
2026-01-23 16:00 - 20:00
Experience the electrifying performance of Joe the Show at Rick’s Bar Downstairs Stage in Key West’s renowned Rick’s Entertainment Complex. Known for his captivating stage presence and versatile musical talent, Joe lights up the stage with energetic live music, making it an unforgettable night for music lovers and nightlife enthusiasts alike.

DALLAS REMINGTON ~ Durty Harry's Stage at Rick's Entertainment Complex
2026-01-23 18:00 - 21:00
Dallas Remington takes center stage at Rick’s Entertainment Complex, captivating the audience with her dynamic musical prowess. Known for her engaging performances, Dallas blends soulful melodies with vibrant energy, creating an unforgettable experience. Join her at Durty Harry’s Stage in Old Town Key West for a night of exceptional live music and electric atmosphere.

Joe the Show ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-23 19:00 - 23:00
Experience the electrifying presence of Joe the Show at Rick’s Bar in Key West’s premier entertainment hub. Known for his captivating performances and magnetic energy, Joe promises an unforgettable night filled with dynamic live music. Join the excitement at Rick’s Entertainment Complex and enjoy a vibrant blend of tunes and nightlife.
