Joe The Show at Sloppy Joe's Bar
2026-01-26 10:00 - 11:45 (America/New_York)
Experience the dynamic talent of Joe The Show at Sloppy Joe’s Bar, where his electrifying performances captivate audiences nightly. Known for his engaging stage presence and musical prowess, Joe brings a unique flair to this historic Key West landmark. Enjoy an unforgettable blend of music, energy, and charisma at this iconic venue.

Webb Dillard ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-26 12:00 - 15:00
Experience the dynamic performances of musician Webb Dillard at Rick’s Bar, nestled in Key West’s vibrant entertainment scene. Renowned for captivating live music, Webb brings energy and flair to the heart of Rick’s Entertainment Complex. Enjoy an unforgettable night as his rhythms enhance the electric atmosphere of this iconic nightlife destination.

Tim Hollohan at Sloppy Joe's Bar
2026-01-26 12:00 - 16:45
Tim Hollohan, a musician from Columbia, South Carolina, captivates audiences almost daily at the iconic Sloppy Joe’s Bar in Key West. Known for his energetic stage presence and engaging interactions, Tim brings a lively vibe to this historic venue. His performances are a must-see experience for bar-goers.

Jay Klein at Schooner Wharf Bar
2026-01-26 12:00 - 17:00
Experience the captivating sounds of musician Jay Klein at Schooner Wharf Bar. Nestled in Key West’s seaport, this open-air venue offers stunning waterfront views, fresh seafood, and vibrant island vibes. Enjoy Klein’s live performance amid a truly local atmosphere, making for an unforgettable evening of music and relaxation.

Just George ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-26 15:00 - 19:00
Experience an unforgettable evening with Just George at Rick’s Bar, located in the vibrant Rick’s Entertainment Complex. As a talented musician, Just George captivates audiences with his dynamic performances, set against the backdrop of Key West’s largest club. Enjoy live music, lively dancing, and the electric atmosphere of Old Town’s entertainment hotspot.

Preacher Pete Presents at Sloppy Joe's Bar
2026-01-26 17:30 - 21:30
Join the legendary Preacher Pete at Sloppy Joe’s Bar for an unforgettable musical experience. Known for his captivating performances, Pete is a Key West icon who creates spontaneous magic with a guest musician. This lively event promises an atmospheric blend of talent and charm, leaving audiences mesmerized in the historic setting.

Joe The Show at Schooner Wharf Bar
2026-01-26 18:30 - 22:30
Experience the captivating performance of Joe The Show at Schooner Wharf Bar in Key West. Known for his dynamic musical talent, Joe brings energy and flair to every show in this laid-back, open-air waterfront venue. Enjoy live music, fresh seafood, and island vibes in a historic seaport bar setting.

Aaron Hudgins ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-26 20:00 - 23:59
Experience the electrifying performance of musician Aaron Hudgins at Rick’s Bar, nestled within Key West’s vibrant Rick’s Entertainment Complex. Renowned for his dynamic presence and captivating sound, Aaron delivers an unforgettable musical journey in Florida’s largest nightlife spot. Dive into an evening of live tunes, great drinks, and incredible energy.

Collette Campbell at Sloppy Joe's Bar
2026-01-27 10:00 - 11:45
Collette Campbell, a talented musician, takes the stage at Sloppy Joe’s Bar, captivating audiences with her dynamic performance from 10:00 am to 11:45 am. Renowned for her engaging presence, Collette brings energy and passion to this historic Key West venue, complementing its lively atmosphere and vibrant entertainment offerings. A must-see act for music lovers.

Brian Roberts at Sloppy Joe's Bar
2026-01-27 12:00 - 16:45
Brian Roberts captivates audiences at Sloppy Joe’s Bar with his dynamic musical performances. Surrounded by the vibrant atmosphere of this historic Key West landmark, Roberts offers an unforgettable live music experience. His talent and charisma make him a standout in the Key West music scene, drawing fans eager for a night of exceptional entertainment.

Oren Polak at Schooner Wharf Bar
2026-01-27 12:00 - 17:00
Oren Polak enchants audiences at the iconic Schooner Wharf Bar with his captivating music. Set in Key West’s historic seaport, this open-air venue features Polak’s dynamic performances, adding to its charm. While enjoying stunning waterfront views and fresh seafood, Polak’s tunes create an unforgettable, laid-back island experience for locals and visitors alike.

Jesse Lee ~Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-27 15:00 - 19:00
Experience the electrifying performance of musician Jesse Lee at Rick’s Bar, nestled within Key West’s largest entertainment hub. Known for his captivating live music, Jesse Lee energizes audiences with his dynamic presence and musical talent. Join him for an unforgettable evening of entertainment at Rick’s Entertainment Complex, where vibrant nightlife meets exceptional artistry.

Gary Hempsey at Schooner Wharf Bar
2026-01-27 18:30 - 22:30
Gary Hempsey delivers captivating live performances at Schooner Wharf Bar in Key West. Known for his engaging stage presence and diverse musical repertoire, Hempsey enchants audiences in this open-air, waterfront venue. His talent, combined with the bar’s vibrant atmosphere and stunning dockside views, makes for an unforgettable entertainment experience.

Izzy Zaidman at Sloppy Joe's Bar
2026-01-28 10:00 - 11:45
Izzy Zaidman, a passionate musician with his Steel Resonator guitar, fills Sloppy Joe’s Bar with the rich sounds of American Roots music. Since moving to Key West in 2021, Izzy has captivated locals and tourists alike, creating an unforgettable atmosphere in this historic landmark on Duval Street.

Brian Roberts at Sloppy Joe's Bar
2026-01-28 12:00 - 16:45
Experience the captivating melodies of Brian Roberts at Sloppy Joe’s Bar, a historic Key West landmark. Renowned for its vibrant atmosphere, the bar comes alive with Roberts’ engaging performances, blending seamlessly into the lively Key West music scene. Enjoy his exceptional talent amidst classic American fare and cocktails in this iconic venue.

Tony Baltimore at Schooner Wharf Bar
2026-01-28 12:00 - 17:00
Experience the captivating talent of musician Tony Baltimore at the iconic Schooner Wharf Bar. Nestled in Key West’s vibrant seaport, Tony’s live performances resonate through the open-air venue. Immerse yourself in his musical prowess while enjoying the laid-back atmosphere, splendid dockside views, and the bar’s renowned seafood and island cuisine delights.

Harley Ray ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-28 15:00 - 19:00
Experience the electrifying performance of musician Harley Ray at Rick’s Bar, located in the heart of Old Town Key West’s vibrant nightlife scene. Known for captivating live music, Harley Ray’s talent shines in the energetic atmosphere of Rick’s Entertainment Complex, making it a must-visit destination for music enthusiasts and partygoers alike.

Jeff Clark at Schooner Wharf Bar
2026-01-28 18:30 - 22:30
Jeff Clark sets the scene at Schooner Wharf Bar with his captivating musical performances. As a talented musician, he enchants audiences with his rhythmic melodies and engaging presence. Nestled in Key West’s historic seaport, the bar offers a relaxed, open-air atmosphere where Clark’s music complements the stunning dockside views and vibrant local ambiance.

Joe the Show ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-28 19:00 - 23:00
Experience the electrifying performance of Joe the Show at Rick’s Bar, nestled in the heart of Old Town Key West. Known for his captivating stage presence, Joe brings live entertainment to life with an unforgettable fusion of music and charisma. Join the vibrant nightlife scene at Rick’s Entertainment Complex for an evening of unparalleled musical delight.

Izzy Zaidman at Sloppy Joe's Bar
2026-01-29 10:00 - 11:45
Izzy Zaidman, a dynamic musician, captivates audiences at Sloppy Joe’s Bar with his soulful American Roots sound. Since relocating to Key West in 2021, his mastery of the Steel Resonator guitar has become a staple of the island’s music scene, creating an unforgettable experience for visitors to this historic venue.

Sid The Bayou Kid at Sloppy Joe's Bar
2026-01-29 12:00 - 16:45
Experience the captivating sounds of Sid The Bayou Kid as he brings his swampy, soulful tunes to Sloppy Joe’s Bar in Key West. With over 30 years of performances spanning from New Orleans to Nashville, Sid enchants audiences with his unique Cajun flair, making every night unforgettable in this historic venue.

Ross Brown at Schooner Wharf Bar
2026-01-29 12:00 - 17:00
Ross Brown, a talented musician, captivates audiences with his lively performances at Schooner Wharf Bar in Key West. With the picturesque backdrop of the seaport, his music resonates through the open-air venue, creating a vibrant and memorable experience. Brown’s engaging tunes perfectly complement the bar’s laid-back, island atmosphere.

Jeff Harris ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-29 15:00 - 19:00
Join talented musician Jeff Harris at Rick’s Bar, nestled within Rick’s Entertainment Complex in Key West. Experience his captivating live performances in Florida’s largest club south of Miami. As Jeff’s music enhances the vibrant nightlife, explore eight famous bars, enjoy dancing, and indulge in endless fun at this lively entertainment hub.

Nick Brownwell at Schooner Wharf Bar
2026-01-29 18:30 - 22:30
Nick Brownwell lights up Schooner Wharf Bar with his captivating performances, blending vibrant rhythms and soulful melodies in Key West’s iconic open-air venue. As a talented musician, Nick’s dynamic sets perfectly complement the bar’s laid-back atmosphere, offering guests an unforgettable experience amidst stunning dockside views and delectable island cuisine.

Andrew B. ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-29 19:00 - 23:00
Join musician Andrew B. at Rick’s Bar Downstairs in Rick’s Entertainment Complex for a captivating night of live music. Known for his dynamic performances, Andrew brings an electrifying energy to Key West’s largest entertainment venue. Experience unforgettable tunes and endless fun in the vibrant heart of Old Town Key West.

Wynn Tayor ~ Rick's Bar Downstairs Stage at Rick's Entertainment Complex
2026-01-30 12:00 - 16:00
Experience the captivating performance of musician Wynn Taylor at Rick’s Bar Downstairs Stage in Rick’s Entertainment Complex. Known for his electrifying presence and musical prowess, Wynn Taylor promises an unforgettable evening filled with soulful tunes in the vibrant heart of Old Town Key West. Dive into a night of live music and spirited atmosphere.

Tim Hollohan at Sloppy Joe's Bar
2026-01-30 12:00 - 16:45
At Sloppy Joe’s Bar, Tim Hollohan captivates audiences with his vibrant stage presence and interactive performances. Originally from Columbia, South Carolina, Tim’s dynamic musical talents have become a staple in Key West. His engaging shows, set against the lively backdrop of this historic venue, make for an unforgettable experience.

Tony Baltimore at Schooner Wharf Bar
2026-01-30 12:00 - 17:00
At the historic Schooner Wharf Bar in Key West, experience the captivating sounds of musician Tony Baltimore. Known for his engaging performances, Tony brings a vibrant energy to this laid-back, open-air venue. Enjoy his live music while soaking in the stunning dockside views and indulging in the bar’s fresh seafood and island cuisine.

Joe the Show ~ Rick's Bar Downstairs Stage at Rick's Entertainment Complex
2026-01-30 16:00 - 20:00
Experience the electrifying performance of Joe the Show at Rick’s Bar Downstairs Stage in Key West’s premier entertainment complex. Known for his dynamic musical talent, Joe captivates audiences with an unforgettable live music experience. Amidst vibrant nightlife, eight bars, and endless fun, Joe’s lively show is a must-see highlight.

DALLAS REMINGTON ~ Durty Harry's Stage at Rick's Entertainment Complex
2026-01-30 18:00 - 21:00
Experience Dallas Remington live at Durty Harry’s Stage in Rick’s Entertainment Complex, Key West’s iconic nightlife venue. Known for her captivating performances, Dallas brings a unique blend of energy and musical talent, ensuring an unforgettable night. Witness her powerful stage presence and enjoy incredible live music in the heart of Old Town Key West.
