Monday, February 23, 2026

• February 23, 2026 10:00 am - 11:45 am

  Joe The Show at Sloppy Joe’s Bar

February 23 @ 10:00 am - 11:45 am
Joe The Show at Sloppy Joe’s Bar
Experience the captivating performance of Joe The Show at Sloppy Joe's Bar, Key West's iconic venue. Renowned for his vibrant stage presence and musical talent,…
Free
• February 23, 2026 12:00 pm - 4:45 pm

  Tim Hollohan at Sloppy Joe’s Bar

February 23 @ 12:00 pm - 4:45 pm
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan captivates audiences at Sloppy Joe's Bar, an iconic venue in Key West. Originally from Columbia, South Carolina, Tim graces the stage almost daily,…
Free
• February 23, 2026 12:00 pm - 5:00 pm

  Jay Klein at Schooner Wharf Bar

February 23 @ 12:00 pm - 5:00 pm
Jay Klein at Schooner Wharf Bar
Experience a captivating evening with musician Jay Klein at the Schooner Wharf Bar. Nestled in Key West's Seaport, this popular venue combines dockside views with…
Free
• February 23, 2026 12:00 pm - 3:00 pm

  Webb Dillard ~ Rick’s Bar Downstairs Stage

February 23 @ 12:00 pm - 3:00 pm
Webb Dillard ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Webb Dillard on Rick's Bar Downstairs Stage at Rick's Entertainment Complex in Old Town Key West. As a talented musician,…
Free
• February 23, 2026 1:00 pm - 4:00 pm

  Rolando Rojas at Sunset Pier

February 23 @ 1:00 pm - 4:00 pm
Rolando Rojas at Sunset Pier
Experience the captivating performances of Rolando Rojas at Sunset Pier. Renowned for his dynamic musical talent, Rojas enchants audiences with his vibrant melodies and charismatic…
Free
• February 23, 2026 1:00 pm - 4:00 pm

  Shastina Chiles at Hank’s Hair of the Dog Saloon

February 23 @ 1:00 pm - 4:00 pm
Shastina Chiles at Hank’s Hair of the Dog Saloon
Enjoy an electrifying evening with musician Shastina Chiles at Hank's Hair of the Dog Saloon in Key West. Known for her captivating performances, Shastina's music…
Free
• February 23, 2026 3:00 pm - 7:00 pm

  Just George ~ Rick’s Bar Downstairs Stage

February 23 @ 3:00 pm - 7:00 pm
Just George ~ Rick’s Bar Downstairs Stage
Experience the phenomenal musical talent of Just George at Rick's Bar Downstairs Stage in Key West. Renowned for his captivating performances and dynamic presence, Just…
Free
• February 23, 2026 5:00 pm - 8:00 pm

  Jay Bangles at Tiki House Key West

February 23 @ 5:00 pm - 8:00 pm
Jay Bangles at Tiki House Key West
Experience the captivating sounds of musician Jay Bangles at Tiki House Key West. Known for his dynamic performances and infectious energy, Jay delivers an unforgettable…
Free
• February 23, 2026 5:00 pm - 8:00 pm

  Scott Morlock at Hank’s Hair of the Dog Saloon

February 23 @ 5:00 pm - 8:00 pm
Scott Morlock at Hank’s Hair of the Dog Saloon
Scott Morlock electrifies Hank's Hair of the Dog Saloon with his dynamic musical talent. A must-see performer, Scott keeps the vibrant Key West nightlife alive…
Free
• February 23, 2026 5:30 pm - 9:30 pm

  Preacher Pete Presents at Sloppy Joe’s Bar

February 23 @ 5:30 pm - 9:30 pm
Preacher Pete Presents at Sloppy Joe’s Bar
Join the legendary Preacher Pete at Sloppy Joe's Bar, where his enchanting musical prowess creates an unforgettable experience. Known for his captivating performances, Pete, alongside…
Free
• February 23, 2026 6:30 pm - 10:30 pm

  Joe The Show at Schooner Wharf Bar

February 23 @ 6:30 pm - 10:30 pm
Joe The Show at Schooner Wharf Bar
Experience the vibrant tunes of Joe The Show at Schooner Wharf Bar, Key West's iconic seaport venue. Known for captivating performances that resonate with both…
Free
• February 23, 2026 6:30 pm - 10:30 pm

  Joe The Show at Schooner Wharf Bar

February 23 @ 6:30 pm - 10:30 pm
Joe The Show at Schooner Wharf Bar
Experience the vibrant tunes of Joe The Show at Schooner Wharf Bar, Key West's iconic seaport venue. Known for captivating performances that resonate with both…
Free
• February 23, 2026 7:00 pm - 11:00 pm

  Charles Miller ~ Rick’s Bar Downstairs Stage

February 23 @ 7:00 pm - 11:00 pm
Charles Miller ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Charles Miller on the Downstairs Stage at Rick's Bar, nestled in the vibrant heart of Old Town Key West.…
Free
• February 23, 2026 7:30 pm - 10:30 pm

  Jay Bangles at Tiki House Key West

February 23 @ 7:30 pm - 10:30 pm
Jay Bangles at Tiki House Key West
Experience the vibrant sounds of musician Jay Bangles at Tiki House Key West. Known for his dynamic performances, Jay captivates audiences with his unique style…
Free
• February 23, 2026 8:00 pm - 11:59 pm

  Gerd Rube at The Bull & Whistle Bar

February 23 @ 8:00 pm - 11:59 pm
Gerd Rube at The Bull & Whistle Bar
Experience the captivating talent of Gerd Rube at The Bull & Whistle Bar in Key West’s lively Old Town. Known for his engaging performances, Rube…
Free
• February 23, 2026 9:00 pm - 11:45 pm

  Josh Kiser at Hank’s Hair of the Dog Saloon

February 23 @ 9:00 pm - 11:45 pm
Josh Kiser at Hank’s Hair of the Dog Saloon
Country musician Josh Kiser brings his electrifying performance to Hank's Hair of the Dog Saloon, captivating audiences with his soulful sound and high-energy stage presence.…
Free

Tuesday, February 24, 2026

• February 24, 2026 12:00 pm - 4:45 pm

  Brian Roberts at Sloppy Joe’s Bar

February 24 @ 12:00 pm - 4:45 pm
Brian Roberts at Sloppy Joe’s Bar
Experience the captivating performance of musician Brian Roberts at Sloppy Joe's Bar, a historic Key West venue on Duval Street. Known for his vibrant energy…
Free
• February 24, 2026 12:00 pm - 5:00 pm

  Oren Polak at Schooner Wharf Bar

February 24 @ 12:00 pm - 5:00 pm
Oren Polak at Schooner Wharf Bar
Experience the captivating performances of musician Oren Polak at Schooner Wharf Bar, located in Key West's historic Seaport. Enjoy his engaging live music in the…
Free
• February 24, 2026 1:00 pm - 4:00 pm

  Billy Ruegger at Sunset Pier

February 24 @ 1:00 pm - 4:00 pm
Billy Ruegger at Sunset Pier
Experience the captivating sounds of musician Billy Ruegger at Sunset Pier in Key West. As the sun sets over the Gulf of Mexico, Ruegger's dynamic…
Free
• February 24, 2026 1:00 pm - 4:00 pm

  Tony Baltimore at Hank’s Hair of the Dog Saloon

February 24 @ 1:00 pm - 4:00 pm
Tony Baltimore at Hank’s Hair of the Dog Saloon
Experience the captivating performance of musician Tony Baltimore at Hank's Hair of the Dog Saloon in Key West. Known for its vibrant atmosphere, this dog-friendly…
Free
• February 24, 2026 1:30 pm - 4:30 pm

  Joe The Show at Tiki House Key West

February 24 @ 1:30 pm - 4:30 pm
Joe The Show at Tiki House Key West
Experience the incredible talent of Joe The Show at Tiki House Key West. This dynamic musician captivates audiences with his electrifying performances, blending exceptional musical…
Free
• February 24, 2026 3:00 pm - 7:00 pm

  Jesse Lee ~Rick’s Bar Downstairs Stage

February 24 @ 3:00 pm - 7:00 pm
Jesse Lee ~Rick’s Bar Downstairs Stage
Experience the captivating musical talent of Jesse Lee Jr at Rick's Bar Downstairs Stage in Key West. Known for his engaging performances and exceptional musicianship,…
Free
• February 24, 2026 5:00 pm - 8:00 pm

  Jay Klein at Hank’s Hair of the Dog Saloon

February 24 @ 5:00 pm - 8:00 pm
Jay Klein at Hank’s Hair of the Dog Saloon
Jay Klein will captivate audiences at Hank's Hair of the Dog Saloon in Key West with his mesmerizing musical performances. Known for his dynamic presence,…
Free
• February 24, 2026 6:30 pm - 10:30 pm

  Gary Hempsey at Schooner Wharf Bar

February 24 @ 6:30 pm - 10:30 pm
Gary Hempsey at Schooner Wharf Bar
Experience the soulful tunes of musician Gary Hempsey at Schooner Wharf Bar, where his captivating performance enhances the open-air vibes of this Key West gem.…
Free
• February 24, 2026 7:00 pm - 11:00 pm

  Joe the Show ~ Rick’s Bar Downstairs Stage

February 24 @ 7:00 pm - 11:00 pm
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Joe the Show at Rick's Bar Downstairs Stage in Key West. Known for his dynamic presence and musical prowess, Joe…
Free
• February 24, 2026 7:30 pm - 10:30 pm

  Aaron Hudgins at Tiki House Key West

February 24 @ 7:30 pm - 10:30 pm
Aaron Hudgins at Tiki House Key West
Experience the electrifying performance of musician Aaron Hudgins at Tiki House Key West. Known for his captivating stage presence and dynamic musical talent, Aaron delivers…
Free
• February 24, 2026 8:00 pm - 11:59 pm

  Marshall Morlock at The Bull & Whistle Bar

February 24 @ 8:00 pm - 11:59 pm
Marshall Morlock at The Bull & Whistle Bar
Experience the captivating performance of Marshall Morlock at The Bull & Whistle Bar, Key West’s iconic nightlife hotspot. Known for his dynamic live music, Morlock…
Free
• February 24, 2026 9:00 pm - 11:45 pm

  Victoria Leigh at Hank’s Hair of the Dog Saloon

February 24 @ 9:00 pm - 11:45 pm
Victoria Leigh at Hank’s Hair of the Dog Saloon
Victoria Leigh is set to captivate the audience at Hank's Hair of the Dog Saloon in Key West. With her soulful melodies and dynamic performance,…
Free

Wednesday, February 25, 2026

• February 25, 2026 10:00 am - 11:45 am

  Izzy Zaidman at Sloppy Joe’s Bar

February 25 @ 10:00 am - 11:45 am
Izzy Zaidman at Sloppy Joe’s Bar
Izzy Zaidman, a talented musician who relocated to Key West in 2021, captivates audiences at Sloppy Joe's Bar with his Steel Resonator guitar. Bringing the…
Free
• February 25, 2026 12:00 pm - 4:45 pm

  Brian Roberts at Sloppy Joe’s Bar

February 25 @ 12:00 pm - 4:45 pm
Brian Roberts at Sloppy Joe’s Bar
Experience the captivating performances of Brian Roberts at Sloppy Joe's Bar, a renowned Key West landmark. Known for his dynamic presence and musical prowess, Roberts…
Free
• February 25, 2026 12:00 pm - 5:00 pm

  Tony Baltimore at Schooner Wharf Bar

February 25 @ 12:00 pm - 5:00 pm
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore captivates audiences at Schooner Wharf Bar with his dynamic musical performances. Nestled in Key West's historic seaport, this open-air gem provides picturesque dockside…
Free
• February 25, 2026 12:00 pm - 5:00 pm

  Tony Baltimore at Schooner Wharf Bar

February 25 @ 12:00 pm - 5:00 pm
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore captivates audiences at Schooner Wharf Bar with his dynamic musical performances. Nestled in Key West's historic seaport, this open-air gem provides picturesque dockside…
Free
• February 25, 2026 1:00 pm - 4:00 pm

  Shastina Chiles at Hank’s Hair of the Dog Saloon

February 25 @ 1:00 pm - 4:00 pm
Shastina Chiles at Hank’s Hair of the Dog Saloon
Shastina Chiles, a talented musician, brings her vibrant energy and soulful tunes to Hank's Hair of the Dog Saloon in Key West. Known for captivating…
Free
• February 25, 2026 2:00 pm - 6:00 pm

  Mac Calhoun at The Bull & Whistle Bar

February 25 @ 2:00 pm - 6:00 pm
Mac Calhoun at The Bull & Whistle Bar
Mac Calhoun captivates audiences at The Bull & Whistle Bar with his dynamic musical performances. Nestled on Key West's vibrant Duval Street, this lively venue…
Free
• February 25, 2026 3:00 pm - 7:00 pm

  Harley Ray ~ Rick’s Bar Downstairs Stage

February 25 @ 3:00 pm - 7:00 pm
Harley Ray ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Harley Ray at Rick's Bar Downstairs Stage. Known for captivating audiences with a unique musical style, Harley Ray delivers an…
Free
• February 25, 2026 5:00 pm - 8:00 pm

  Jay Bangles at Tiki House Key West

February 25 @ 5:00 pm - 8:00 pm
Jay Bangles at Tiki House Key West
Experience the captivating sounds of musician Jay Bangles at Tiki House Key West. Known for his vibrant performances, Jay blends various musical styles to create…
Free
• February 25, 2026 5:00 pm - 8:00 pm

  Kari Wolf and Gigi at Hank’s Hair of the Dog Saloon

February 25 @ 5:00 pm - 8:00 pm
Kari Wolf and Gigi at Hank’s Hair of the Dog Saloon
Kari Wolf captivates audiences with soulful melodies and dynamic performances at Hank's Hair of the Dog Saloon. Known for her engaging stage presence, Kari enchants…
Free
• February 25, 2026 6:30 pm - 10:30 pm

  Jeff Clark at Schooner Wharf Bar

February 25 @ 6:30 pm - 10:30 pm
Jeff Clark at Schooner Wharf Bar
Jeff Clark enchants audiences at Schooner Wharf Bar with his captivating musical performances. Against the backdrop of Key West's stunning seaport, his skillful tunes create…
Free
• February 25, 2026 7:00 pm - 11:00 pm

  Andrew B. ~ Rick’s Bar Downstairs Stage

February 25 @ 7:00 pm - 11:00 pm
Andrew B. ~ Rick’s Bar Downstairs Stage
Andrew B., a captivating musician, takes center stage at Rick's Bar Downstairs in Key West's largest entertainment venue. Known for his dynamic performances, Andrew B.…
Free
• February 25, 2026 7:30 pm - 10:30 pm

  Jay Bangles at Tiki House Key West

February 25 @ 7:30 pm - 10:30 pm
Jay Bangles at Tiki House Key West
Experience the mesmerizing sounds of Jay Bangles at Tiki House Key West. This talented musician captivates audiences with his unique style and dynamic performances. Enjoy…
Free
• February 25, 2026 8:00 pm - 11:59 pm

  Kristen McNamara at The Bull & Whistle Bar

February 25 @ 8:00 pm - 11:59 pm
Kristen McNamara at The Bull & Whistle Bar
Experience the enchanting performance of Kristen McNamara at The Bull & Whistle Bar. Known for her captivating voice and dynamic stage presence, Kristen enthralls audiences…
Free

Thursday, February 26, 2026

• February 26, 2026 11:00 am - 3:00 pm

  Trenton Chandler ~ Rick’s DownStairs Stage

February 26 @ 11:00 am - 3:00 pm
Trenton Chandler ~ Rick’s DownStairs Stage
Experience the heartfelt tunes of Trenton Chandler at Rick's DownStairs Stage in Key West. A Shallowater, Texas native, Trenton channels the spirit of legends like…
Free
• February 26, 2026 12:00 pm - 4:45 pm

  Sid The Bayou Kid at Sloppy Joe’s Bar

February 26 @ 12:00 pm - 4:45 pm
Sid The Bayou Kid at Sloppy Joe’s Bar
Sid The Bayou Kid, a charismatic musician from Thibodaux, LA, captivates audiences with his swamp-infused sound. With over 30 years of experience, Sid brings his…
Free
• February 26, 2026 12:00 pm - 5:00 pm

  Ross Brown at Schooner Wharf Bar

February 26 @ 12:00 pm - 5:00 pm
Ross Brown at Schooner Wharf Bar
Ross Brown brings his musical talents to the Schooner Wharf Bar, a beloved Key West venue renowned for its vibrant live music scene. In this…
Free
• February 26, 2026 12:00 pm - 5:00 pm

  Ross Brown at Schooner Wharf Bar

February 26 @ 12:00 pm - 5:00 pm
Ross Brown at Schooner Wharf Bar
Ross Brown brings his musical talents to the Schooner Wharf Bar, a beloved Key West venue renowned for its vibrant live music scene. In this…
Free
• February 26, 2026 1:00 pm - 4:00 pm

  Marjory Lee at Sunset Pier

February 26 @ 1:00 pm - 4:00 pm
Marjory Lee at Sunset Pier
Experience the enchanting sounds of Marjory Lee at Sunset Pier, where her captivating performances enhance Key West's vibrant atmosphere. Nestled at the Ocean Key Resort,…
Free
• February 26, 2026 1:00 pm - 4:00 pm

  Tony Baltimore at Hank’s Hair of the Dog Saloon

February 26 @ 1:00 pm - 4:00 pm
Tony Baltimore at Hank’s Hair of the Dog Saloon
Tony Baltimore, a captivating musician, brings his vibrant performances to Hank's Hair of the Dog Saloon in Key West. Known for his engaging live sets,…
Free
• February 26, 2026 2:00 pm - 5:00 pm

  Jefff Clark at Tiki House Key West

February 26 @ 2:00 pm - 5:00 pm
Jefff Clark at Tiki House Key West
Join us at the Tiki House Key West for an unforgettable musical experience with Jefff Clark. A talented musician known for his captivating performances, Jefff…
Free
• February 26, 2026 3:00 pm - 7:00 pm

  Jeff Harris ~ Rick’s Bar Downstairs Stage

February 26 @ 3:00 pm - 7:00 pm
Jeff Harris ~ Rick’s Bar Downstairs Stage
Experience the mesmerizing talents of musician Jeff Harris on the Downstairs Stage at Rick's Bar, located in Key West's largest entertainment venue. Known for his…
Free
• February 26, 2026 5:00 pm - 8:00 pm

  Elle Haley at Hank’s Hair of the Dog Saloon

February 26 @ 5:00 pm - 8:00 pm
Elle Haley at Hank’s Hair of the Dog Saloon
Elle Haley captivates audiences with her electrifying performances at Hank's Hair of the Dog Saloon in Key West. Known for her soulful voice and dynamic…
Free
• February 26, 2026 6:30 pm - 10:30 pm

  Nick Brownell at Schooner Wharf Bar

February 26 @ 6:30 pm - 10:30 pm
Nick Brownell at Schooner Wharf Bar
Nick Brownell, an engaging musician, performs live at the Schooner Wharf Bar, a beloved waterfront venue in Key West. Known for his vibrant music, Nick…
Free
• February 26, 2026 6:30 pm - 10:30 pm

  Nick Brownell at Schooner Wharf Bar

February 26 @ 6:30 pm - 10:30 pm
Nick Brownell at Schooner Wharf Bar
Nick Brownell, an engaging musician, performs live at the Schooner Wharf Bar, a beloved waterfront venue in Key West. Known for his vibrant music, Nick…
Free
• February 26, 2026 7:00 pm - 11:00 pm

  Joe the Show ~ Rick’s Bar Downstairs Stage

February 26 @ 7:00 pm - 11:00 pm
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the electrifying energy of Joe the Show at Rick's Bar Downstairs Stage. This talented musician captivates audiences with his dynamic performances, making every night…
Free
• February 26, 2026 8:00 pm - 11:59 pm

  Sandra Lee at The Bull & Whistle Bar

February 26 @ 8:00 pm - 11:59 pm
Sandra Lee at The Bull & Whistle Bar
Join musician Sandra Lee at The Bull & Whistle Bar in Key West's Old Town. Known for her captivating performances, Sandra Lee combines talent and…
Free
• February 26, 2026 9:00 pm - 11:45 pm

  Barrett Thomas at Hank’s Hair of the Dog Saloon

February 26 @ 9:00 pm - 11:45 pm
Barrett Thomas at Hank’s Hair of the Dog Saloon
Barrett Thomas captivates audiences at Hank's Hair of the Dog Saloon with his soulful tunes and engaging performances. Known for creating a vibrant atmosphere, Barrett's…
Free

Friday, February 27, 2026

• February 27, 2026 12:00 pm - 4:45 pm

  Tim Hollohan at Sloppy Joe’s Bar

February 27 @ 12:00 pm - 4:45 pm
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan, originally from Columbia, South Carolina, captivates audiences at Key West's historic Sloppy Joe's Bar with his engaging performances. A staple in the local…
Free
• February 27, 2026 12:00 pm - 5:00 pm

  Tony Baltimore at Schooner Wharf Bar

February 27 @ 12:00 pm - 5:00 pm
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore captivates audiences at Schooner Wharf Bar, an iconic Key West venue known for its laid-back ambiance and stunning dockside views. With engaging performances…
Free
• February 27, 2026 12:00 pm - 5:00 pm

  Tony Baltimore at Schooner Wharf Bar

February 27 @ 12:00 pm - 5:00 pm
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore captivates audiences at Schooner Wharf Bar, an iconic Key West venue known for its laid-back ambiance and stunning dockside views. With engaging performances…
Free
• February 27, 2026 12:00 pm - 4:00 pm

  Wynn Tayor ~ Rick’s Bar Downstairs Stage

February 27 @ 12:00 pm - 4:00 pm
Wynn Tayor ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of Wynn Taylor at Rick's Bar Downstairs Stage. Located in the heart of Old Town Key West, this renowned musician brings…
Free
• February 27, 2026 1:00 pm - 4:00 pm

  Jockey Jord at Sunset Pier

February 27 @ 1:00 pm - 4:00 pm
Jockey Jord at Sunset Pier
Experience the vibrant energy of Jockey Jord at Sunset Pier, where this talented musician captivates audiences with his live performances. Set against stunning Gulf of…
Free
• February 27, 2026 1:00 pm - 4:00 pm

  Nick Norman at Hank’s Hair of the Dog Saloon

February 27 @ 1:00 pm - 4:00 pm
Nick Norman at Hank’s Hair of the Dog Saloon
Join musician Nick Norman at Hank's Hair of the Dog Saloon in Key West for an unforgettable evening of live music. With his captivating performances,…
Free
• February 27, 2026 3:00 pm - 6:00 pm

  Kari Wolf at Tiki House Key West

February 27 @ 3:00 pm - 6:00 pm
Kari Wolf at Tiki House Key West
Experience the captivating performance of musician Kari Wolf at the vibrant Tiki House Key West. Renowned for her soulful melodies and dynamic stage presence, Kari…
Free
• February 27, 2026 4:00 pm - 8:00 pm

  Joe the Show ~ Rick’s Bar Downstairs Stage

February 27 @ 4:00 pm - 8:00 pm
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Joe the Show at Rick's Bar Downstairs Stage in Old Town Key West. Known for his dynamic musical style and…
Free
• February 27, 2026 5:00 pm - 8:00 pm

  Barrett Thomas at Hank’s Hair of the Dog Saloon

February 27 @ 5:00 pm - 8:00 pm
Barrett Thomas at Hank’s Hair of the Dog Saloon
Barrett Thomas, a captivating musician, brings his vibrant energy and soulful tunes to Hank's Hair of the Dog Saloon in Key West. Enjoy his engaging…
Free
• February 27, 2026 6:00 pm - 9:00 pm

  JOE THE SHOW ~ Durty Harry’s Stage

February 27 @ 6:00 pm - 9:00 pm
JOE THE SHOW ~ Durty Harry’s Stage
Experience an unforgettable evening with Joe The Show at Durty Harry's Stage, located within Rick's Entertainment Complex in Key West. As a captivating musician, Joe…
Free
• February 27, 2026 6:30 pm - 9:30 pm

  Turner Harrison at Tiki House Key West

February 27 @ 6:30 pm - 9:30 pm
Turner Harrison at Tiki House Key West
Enjoy an unforgettable evening with Turner Harrison at Tiki House Key West. Known for his charismatic stage presence and soulful melodies, Turner blends rock, folk,…
Free
• February 27, 2026 8:00 pm - 11:59 pm

  Elle Haley ~ Rick’s Bar Downstairs Stage

February 27 @ 8:00 pm - 11:59 pm
Elle Haley ~ Rick’s Bar Downstairs Stage
Experience the captivating talents of musician Elle Haley at Rick's Bar Downstairs Stage, located in the vibrant Rick's Entertainment Complex in Old Town Key West.…
Free
• February 27, 2026 9:00 pm - 11:45 pm

  Nick Brownell, Shane Sanders and Haden Carpenter at Hank’s Hair of the Dog Saloon

February 27 @ 9:00 pm - 11:45 pm
Nick Brownell, Shane Sanders and Haden Carpenter at Hank’s Hair of the Dog Saloon
Nick Brownell headlines an unforgettable night of live music at Hank's Hair of the Dog Saloon in Key West, supported by Shane Sanders and Haden…
Free

Saturday, February 28, 2026

• February 28, 2026 10:00 am - 11:45 am

  Justin Angelo at Sloppy Joe’s Bar

February 28 @ 10:00 am - 11:45 am
Justin Angelo at Sloppy Joe’s Bar
Experience the captivating performance of Justin Angelo at Sloppy Joe's Bar, a historic landmark in Key West. Known for his unique blend of folk and…
Free
• February 28, 2026 12:00 pm - 4:45 pm

  Jeff Clark at Sloppy Joe’s Bar

February 28 @ 12:00 pm - 4:45 pm
Jeff Clark at Sloppy Joe’s Bar
Jeff Clark, a captivating musician, brings his vibrant performances to Sloppy Joe's Bar, a beloved Key West institution since 1937. Known for its lively atmosphere…
Free
• February 28, 2026 12:00 pm - 5:00 pm

  Nick Brownell at Schooner Wharf Bar

February 28 @ 12:00 pm - 5:00 pm
Nick Brownell at Schooner Wharf Bar
Nick Brownell graces the stage at Schooner Wharf Bar, captivating audiences with his musical talent in Key West's historic waterfront setting. Known for his engaging…
Free
• February 28, 2026 12:00 pm - 5:00 pm

  Nick Brownell at Schooner Wharf Bar

February 28 @ 12:00 pm - 5:00 pm
Nick Brownell at Schooner Wharf Bar
Nick Brownell graces the stage at Schooner Wharf Bar, captivating audiences with his musical talent in Key West's historic waterfront setting. Known for his engaging…
Free
• February 28, 2026 12:00 pm - 4:00 pm

  Zack Seemiller ~ Rick’s Bar Downstairs Stage

February 28 @ 12:00 pm - 4:00 pm
Zack Seemiller ~ Rick’s Bar Downstairs Stage
Join musician Zack Seemiller at Rick's Bar Downstairs Stage in Old Town Key West. Known for his captivating performances, Zack delivers an electrifying mix of…
Free
• February 28, 2026 12:00 pm - 3:00 pm

  Marjorie Lee at Hank’s Hair of the Dog Saloon

February 28 @ 12:00 pm - 3:00 pm
Marjorie Lee at Hank’s Hair of the Dog Saloon
Marjorie Lee captivates audiences at Hank's Hair of the Dog Saloon in Key West with her dynamic performances. Known for her soulful melodies and engaging…
Free
• February 28, 2026 1:00 pm - 4:00 pm

  Meghan Barter at Sunset Pier

February 28 @ 1:00 pm - 4:00 pm
Meghan Barter at Sunset Pier
Experience the enchanting sounds of musician Meghan Barter at Sunset Pier, where her captivating live performances elevate your waterfront dining experience. Nestled in Key West's…
Free
• February 28, 2026 1:30 pm - 4:30 pm

  Joe The Show at Tiki House Key West

February 28 @ 1:30 pm - 4:30 pm
Joe The Show at Tiki House Key West
Experience an unforgettable evening with Joe The Show at Tiki House Key West. Known for his captivating performance and musical prowess, Joe delivers an electrifying…
Free
• February 28, 2026 2:00 pm - 6:00 pm

  Eric Ripper at The Bull & Whistle Bar

February 28 @ 2:00 pm - 6:00 pm
Eric Ripper at The Bull & Whistle Bar
Experience the captivating sounds of musician Eric Ripper at The Bull & Whistle Bar, a lively venue in Key West’s Old Town. Known for his…
Free
• February 28, 2026 3:30 pm - 5:30 pm

  Eric Ripper at Hank’s Hair of the Dog Saloon

February 28 @ 3:30 pm - 5:30 pm
Eric Ripper at Hank’s Hair of the Dog Saloon
Experience the dynamic performance of Eric Ripper at Hank's Hair of the Dog Saloon in Key West. Known for his captivating live music, Eric fills…
Free
• February 28, 2026 4:00 pm - 8:00 pm

  Bradd Shadduck ~ Rick’s Bar Downstairs Stage

February 28 @ 4:00 pm - 8:00 pm
Bradd Shadduck ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of Bradd Shadduck on the Downstairs Stage at Rick's Bar, nestled in Old Town Key West. As a talented musician, Bradd…
Free
• February 28, 2026 5:30 pm - 8:30 pm

  Elle Haley at Tiki House Key West

February 28 @ 5:30 pm - 8:30 pm
Elle Haley at Tiki House Key West
Experience the captivating sounds of Elle Haley, a talented musician known for her enchanting performances, at Tiki House Key West. Her soulful melodies and vibrant…
Free
• February 28, 2026 5:30 pm - 8:30 pm

  Sunset Blues w/ Andy Westcott at Sunset Pier

February 28 @ 5:30 pm - 8:30 pm
Sunset Blues w/ Andy Westcott at Sunset Pier
Experience the soulful melodies of musician Andy Westcott at Sunset Pier in Key West. Against the backdrop of breathtaking sunsets and ocean views, Andy's blues…
Free
• February 28, 2026 9:00 pm - 11:45 pm

  Aaron Hudgins and Sharese at Hank’s Hair of the Dog Saloon

February 28 @ 9:00 pm - 11:45 pm
Aaron Hudgins and Sharese at Hank’s Hair of the Dog Saloon
Aaron Hudgins mesmerizes audiences at Hank's Hair of the Dog Saloon in Key West with his captivating performances. Known for his dynamic musical talent, Aaron…
Free

Sunday, March 1, 2026

No events on this day.