Monday, February 23, 2026

• 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 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 2:00 pm - 6:00 pm

  Derek Dunbar at The Bull & Whistle Bar

February 23 @ 2:00 pm - 6:00 pm
Derek Dunbar at The Bull & Whistle Bar
Derek Dunbar brings his electrifying presence to The Bull & Whistle Bar, captivating audiences with dynamic performances and exceptional musical talent. His engaging style complements…
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 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 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 - 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

  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 2:00 pm - 6:00 pm

  Jessie Cotton Stone at The Bull & Whistle Bar

February 24 @ 2:00 pm - 6:00 pm
Jessie Cotton Stone at The Bull & Whistle Bar
Jessie Cotton Stone electrifies the atmosphere at The Bull & Whistle Bar in Key West’s Old Town. Known for his captivating performances, Jessie brings a…
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 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

Wednesday, February 25, 2026

• 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 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 - 11:59 pm

  Magic Of Frank Everhart at Schooner Wharf Bar

February 25 @ 7:00 pm - 11:59 pm
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at the iconic Schooner Wharf Bar in Key West. Frank Everhart captivates audiences with mesmerizing illusions and charming…
Free
• February 25, 2026 7:00 pm - 11:59 pm

  Magic Of Frank Everhart at Schooner Wharf Bar

February 25 @ 7:00 pm - 11:59 pm
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West's Seaport. A master magician, Everhart captivates audiences with mesmerizing illusions and…
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
• February 25, 2026 9:00 pm - 11:45 pm

  Pierce August at Hank’s Hair of the Dog Saloon

February 25 @ 9:00 pm - 11:45 pm
Pierce August at Hank’s Hair of the Dog Saloon
Experience the captivating performances of Pierce August at Hank's Hair of the Dog Saloon in vibrant Key West. With electrifying live music, Pierce August transforms…
Free

Thursday, February 26, 2026

• 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

  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 - 6:00 pm

  David Warren at The Bull & Whistle Bar

February 26 @ 2:00 pm - 6:00 pm
David Warren at The Bull & Whistle Bar
Experience an unforgettable night at The Bull & Whistle Bar with David Warren, a captivating entertainer known for his dynamic performances. His music creates an…
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 - 9:00 pm

  Catch The Mania Trivia at Brady’s Pub

February 26 @ 7:00 pm - 9:00 pm
Catch The Mania Trivia at Brady’s Pub
Join us at Brady's Pub for Catch The Mania Trivia, hosted by an enigmatic entertainer who promises a night of fun and excitement. Dive into…
Free
• February 26, 2026 7:00 pm - 11:59 pm

  Magic Of Frank Everhart at Schooner Wharf Bar

February 26 @ 7:00 pm - 11:59 pm
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar, where Frank dazzles audiences with his spellbinding performances. Nestled in Key West's historic seaport,…
Free
• February 26, 2026 7:00 pm - 11:59 pm

  Magic Of Frank Everhart at Schooner Wharf Bar

February 26 @ 7:00 pm - 11:59 pm
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West's Seaport. A master magician, Everhart captivates audiences with mesmerizing illusions and…
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 - 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 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 2:00 pm - 6:00 pm

  Jessie Cotton Stone at The Bull & Whistle Bar

February 27 @ 2:00 pm - 6:00 pm
Jessie Cotton Stone at The Bull & Whistle Bar
Experience the captivating performance of Jessie Cotton Stone at The Bull & Whistle Bar, a lively venue on Key West’s Duval Street. Known for his…
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 6:30 pm - 11:30 pm

  Christopher Dean Band at Schooner Wharf Bar

February 27 @ 6:30 pm - 11:30 pm
Christopher Dean Band at Schooner Wharf Bar
Experience the electrifying performance of the Christopher Dean Band at Schooner Wharf Bar, Key West's iconic waterfront venue. Known for their captivating live shows, the…
Free
• February 27, 2026 6:30 pm - 11:30 pm

  Christopher Dean Band at Schooner Wharf Bar

February 27 @ 6:30 pm - 11:30 pm
Christopher Dean Band at Schooner Wharf Bar
Experience the electrifying performance of the Christopher Dean Band at Schooner Wharf Bar, Key West's iconic waterfront venue. Known for their captivating live shows, the…
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 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 - 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 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 6:30 pm - 11:30 pm

  Christopher Dean Band at Schooner Wharf Bar

February 28 @ 6:30 pm - 11:30 pm
Christopher Dean Band at Schooner Wharf Bar
Experience the soulful sounds of the Christopher Dean Band at the historic Schooner Wharf Bar. Known for their captivating live performances, the band delivers a…
Free
• February 28, 2026 6:30 pm - 11:30 pm

  Christopher Dean Band at Schooner Wharf Bar

February 28 @ 6:30 pm - 11:30 pm
Christopher Dean Band at Schooner Wharf Bar
Experience the soulful sounds of the Christopher Dean Band at the historic Schooner Wharf Bar. Known for their captivating live performances, the band delivers a…
Free
• February 28, 2026 7:00 pm - 11:59 pm

  Magic Of Frank Everhart at Schooner Wharf Bar

February 28 @ 7:00 pm - 11:59 pm
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West's Seaport. Renowned for his captivating performances, Frank Everhart mesmerizes audiences with…
Free
• February 28, 2026 7:00 pm - 11:59 pm

  Magic Of Frank Everhart at Schooner Wharf Bar

February 28 @ 7:00 pm - 11:59 pm
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West's Seaport. A master magician, Everhart captivates audiences with mesmerizing illusions and…
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.