Monday, February 9, 2026

No events on this day.

Tuesday, February 10, 2026

No events on this day.

Wednesday, February 11, 2026

No events on this day.

Thursday, February 12, 2026

• February 12, 2026 12:00 pm - 5:00 pm

  Ross Brown at Schooner Wharf Bar

February 12 @ 12:00 pm - 5:00 pm
Ross Brown at Schooner Wharf Bar
Experience the captivating live performance of musician Ross Brown at the iconic Schooner Wharf Bar in Key West's Seaport. Enjoy his soulful melodies in a…
Free
• February 12, 2026 12:00 pm - 4:45 pm

  Sid The Bayou Kid at Sloppy Joe’s Bar

February 12 @ 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 12, 2026 3:00 pm - 7:00 pm

  Jeff Harris ~ Rick’s Bar Downstairs Stage

February 12 @ 3:00 pm - 7:00 pm
Jeff Harris ~ Rick’s Bar Downstairs Stage
Experience the captivating sounds of musician Jeff Harris as he takes the stage at Rick's Bar Downstairs, nestled in Key West's vibrant Old Town. Known…
Free
• February 12, 2026 6:30 pm - 10:30 pm

  Nick Brownell at Schooner Wharf Bar

February 12 @ 6:30 pm - 10:30 pm
Nick Brownell at Schooner Wharf Bar
Nick Brownell enchants audiences at Schooner Wharf Bar with his captivating musical performances. Nestled in Key West's historic seaport, this open-air venue is the perfect…
Free
• February 12, 2026 7:00 pm - 11:00 pm

  Joe the Show ~ Rick’s Bar Downstairs Stage

February 12 @ 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. Known for his dynamic presence and captivating musical talent, Joe brings an…
Free

Friday, February 13, 2026

• February 13, 2026 11:00 am - 2:30 pm

  Jeff Harris at Irish Kevin’s Bar

February 13 @ 11:00 am - 2:30 pm
Jeff Harris at Irish Kevin’s Bar
Experience the electrifying performances of Jeff Harris at Irish Kevin’s Bar, where his captivating live music brings the crowd to life. Situated in Key West’s…
Free
• February 13, 2026 12:00 pm - 4:45 pm

  Tim Hollohan at Sloppy Joe’s Bar

February 13 @ 12:00 pm - 4:45 pm
Tim Hollohan at Sloppy Joe’s Bar
Experience the vibrant energy of Tim Hollohan at Sloppy Joe's Bar, Key West. Originally from Columbia, South Carolina, Tim graces this iconic venue with captivating…
Free
• February 13, 2026 12:00 pm - 5:00 pm

  Tony Baltimore at Schooner Wharf Bar

February 13 @ 12:00 pm - 5:00 pm
Tony Baltimore at Schooner Wharf Bar
Experience the captivating rhythms of Tony Baltimore at the Schooner Wharf Bar in Key West. Known for his dynamic performances, Tony enchants audiences with his…
Free
• February 13, 2026 12:00 pm - 4:00 pm

  Wynn Tayor ~ Rick’s Bar Downstairs Stage

February 13 @ 12:00 pm - 4:00 pm
Wynn Tayor ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Wynn Taylor at Rick's Bar Downstairs Stage in Key West's iconic Rick's Entertainment Complex. Known for his engaging and…
Free
• February 13, 2026 2:30 pm - 6:30 pm

  Mylo O’Maolain at Irish Kevin’s Bar

February 13 @ 2:30 pm - 6:30 pm
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain is a captivating musician performing at Irish Kevin’s Bar. Known for his engaging live shows and infectious energy, Mylo expertly blends traditional tunes…
Free
• February 13, 2026 4:00 pm - 8:00 pm

  Joe the Show ~ Rick’s Bar Downstairs Stage

February 13 @ 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 Key West. As a captivating musician, Joe brings unparalleled energy and…
Free
• February 13, 2026 5:00 pm - 8:00 pm

  Barrett Thomas at Hank’s Hair of the Dog Saloon

February 13 @ 5:00 pm - 8:00 pm
Barrett Thomas at Hank’s Hair of the Dog Saloon
Experience the captivating performance of musician Barrett Thomas at Hank's Hair of the Dog Saloon in Key West. Known for his engaging live music, Barrett's…
Free
• February 13, 2026 6:00 pm - 9:00 pm

  JOE THE SHOW ~ Durty Harry’s Stage

February 13 @ 6:00 pm - 9:00 pm
JOE THE SHOW ~ Durty Harry’s Stage
Experience the electrifying performance of Joe The Show at Durty Harry's Stage, located within Rick's Entertainment Complex. Known for captivating audiences with his dynamic musical…
Free
• February 13, 2026 6:30 pm - 10:30 pm

  NY Pauly at Irish Kevin’s Bar

February 13 @ 6:30 pm - 10:30 pm
NY Pauly at Irish Kevin’s Bar
NY Pauly is the charismatic musician lighting up the stage at Irish Kevin’s Bar in Key West’s Old Town. Known for his energetic performances and…
Free
• February 13, 2026 6:30 pm - 9:30 pm

  Turner Harrison at Tiki House Key West

February 13 @ 6:30 pm - 9:30 pm
Turner Harrison at Tiki House Key West
Experience an unforgettable evening at Tiki House Key West with the vibrant Turner Harrison. Known for his captivating performances and dynamic stage presence, Turner effortlessly…
Free
• February 13, 2026 8:00 pm - 11:59 pm

  Elle Haley ~ Rick’s Bar Downstairs Stage

February 13 @ 8:00 pm - 11:59 pm
Elle Haley ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Elle Haley at Rick's Bar Downstairs Stage. Known for her dynamic presence and mesmerizing vocals, Elle brings an unforgettable…
Free
• February 13, 2026 9:00 pm - 11:55 pm

  Victoria Leigh at Hank’s Hair of the Dog Saloon

February 13 @ 9:00 pm - 11:55 pm
Victoria Leigh at Hank’s Hair of the Dog Saloon
Victoria Leigh captivates audiences at Hank's Hair of the Dog Saloon with her mesmerizing musical performances. Known for her soulful voice and vibrant stage presence,…
Free

Saturday, February 14, 2026

• February 14, 2026 10:00 am - 11:45 am

  Justin Angelo at Sloppy Joe’s Bar

February 14 @ 10:00 am - 11:45 am
Justin Angelo at Sloppy Joe’s Bar
Justin Angelo, a rising star known in the Lancaster, PA, and Key West music scenes, captivates audiences at Sloppy Joe's Bar with his unique blend…
Free
• February 14, 2026 11:00 am - 2:30 pm

  Jeff Harris at Irish Kevin’s Bar

February 14 @ 11:00 am - 2:30 pm
Jeff Harris at Irish Kevin’s Bar
Experience the vibrant sounds of Jeff Harris at Irish Kevin’s Bar, where his electrifying performances captivate audiences amid Key West’s Old Town. Known for his…
Free
• February 14, 2026 12:00 pm - 4:45 pm

  Ross Brown at Sloppy Joe’s Bar

February 14 @ 12:00 pm - 4:45 pm
Ross Brown at Sloppy Joe’s Bar
Ross Brown, a talented musician based in Key West, FL, captivates audiences at Sloppy Joe's Bar with his masterful guitar, percussion, and vocal skills. Performing…
Free
• February 14, 2026 12:00 pm - 5:00 pm

  Nick Brownell at Schooner Wharf Bar

February 14 @ 12:00 pm - 5:00 pm
Nick Brownell at Schooner Wharf Bar
Nick Brownell brings his musical talents to the Schooner Wharf Bar, captivating audiences with his lively performances amidst the picturesque surroundings of Key West's Seaport.…
Free
• February 14, 2026 12:00 pm - 4:00 pm

  Zack Seemiller ~ Rick’s Bar Downstairs Stage

February 14 @ 12:00 pm - 4:00 pm
Zack Seemiller ~ Rick’s Bar Downstairs Stage
Experience the captivating musical artistry of Zack Seemiller at Rick's Bar Downstairs Stage. Known for his dynamic performances and engaging presence, Zack delivers an unforgettable…
Free
• February 14, 2026 12:00 pm - 3:00 pm

  Marjorie Lee at Hank’s Hair of the Dog Saloon

February 14 @ 12:00 pm - 3:00 pm
Marjorie Lee at Hank’s Hair of the Dog Saloon
Marjorie Lee enchants audiences at Hank's Hair of the Dog Saloon with her captivating musical performances. Known for her soulful voice and dynamic stage presence,…
Free
• February 14, 2026 1:30 pm - 4:30 pm

  Joe The Show at Tiki House Key West

February 14 @ 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. Known for his electrifying performances and musical prowess, Joe captivates audiences with…
Free
• February 14, 2026 2:30 pm - 6:30 pm

  NY Pauly at Irish Kevin’s Bar

February 14 @ 2:30 pm - 6:30 pm
NY Pauly at Irish Kevin’s Bar
Experience the dynamic performance of NY Pauly at Irish Kevin's Bar! Renowned for his engaging live music and energetic crowd interaction, NY Pauly captivates audiences…
Free
• February 14, 2026 3:30 pm - 5:30 pm

  Eric Ripper at Hank’s Hair of the Dog Saloon

February 14 @ 3:30 pm - 5:30 pm
Eric Ripper at Hank’s Hair of the Dog Saloon
Experience the electrifying performance of Eric Ripper at Hank's Hair of the Dog Saloon, a lively hotspot in Key West. As a captivating musician, Eric…
Free
• February 14, 2026 4:00 pm - 8:00 pm

  Bradd Shadduck ~ Rick’s Bar Downstairs Stage

February 14 @ 4:00 pm - 8:00 pm
Bradd Shadduck ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Bradd Shadduck at Rick's Bar Downstairs Stage, where his engaging melodies and dynamic presence light up the venue. Nestled…
Free
• February 14, 2026 5:30 pm - 8:30 pm

  Sunset Blues w/ Andy Westcott at Sunset Pier

February 14 @ 5:30 pm - 8:30 pm
Sunset Blues w/ Andy Westcott at Sunset Pier
Experience the soulful sounds of Andy Westcott as he takes the stage at Sunset Pier in Key West. With his captivating blues performances, Andy brings…
Free
• February 14, 2026 6:00 pm - 9:00 pm

  Elle Haley at Tiki House Key West

February 14 @ 6:00 pm - 9:00 pm
Elle Haley at Tiki House Key West
Experience an unforgettable evening with Elle Haley at Tiki House Key West. Known for her captivating performances and musical talent, Elle brings a unique blend…
Free
• February 14, 2026 6:00 pm - 8:30 pm

  Kristen McNamara at Hank’s Hair of the Dog Saloon

February 14 @ 6:00 pm - 8:30 pm
Kristen McNamara at Hank’s Hair of the Dog Saloon
Kristen McNamara brings her captivating musical talent to Hank's Hair of the Dog Saloon, offering an unforgettable live performance. Known for her dynamic voice and…
Free
• February 14, 2026 6:30 pm - 10:30 pm

  Irish Kevin at Irish Kevin’s Bar

February 14 @ 6:30 pm - 10:30 pm
Irish Kevin at Irish Kevin’s Bar
Experience the infectious energy of Irish Kevin at Irish Kevin's Bar in Key West's Old Town. As a charismatic musician, Irish Kevin captivates audiences with…
Free
• February 14, 2026 8:00 pm - 10:00 pm

  Ray Fogg And Reese Dailey at Key West Theater

February 14 @ 8:00 pm - 10:00 pm
Ray Fogg And Reese Dailey at Key West Theater
Join renowned musician Ray Fogg at the Key West Theater for an unforgettable evening of live music. Known for his engaging stage presence and impressive…
$
• February 14, 2026 9:00 pm - 11:45 pm

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

February 14 @ 9:00 pm - 11:45 pm
Aaron Hudgins and Pierce August at Hank’s Hair of the Dog Saloon
Aaron Hudgins energizes Hank's Hair of the Dog Saloon in Key West with his captivating musical performances, setting the stage for an unforgettable evening. This…
Free

Sunday, February 15, 2026

• February 15, 2026 10:00 am - 11:45 am

  Chris Thomas at Sloppy Joe’s Bar

February 15 @ 10:00 am - 11:45 am
Chris Thomas at Sloppy Joe’s Bar
Renowned musician Chris Thomas electrifies audiences at Sloppy Joe's Bar, a historic Key West landmark. Known for his captivating performances, Thomas brings a dynamic blend…
Free
• February 15, 2026 11:00 am - 2:30 pm

  Bradd Shadduck at Irish Kevin’s Bar

February 15 @ 11:00 am - 2:30 pm
Bradd Shadduck at Irish Kevin’s Bar
Experience the dynamic energy of musician Bradd Shadduck at Irish Kevin’s Bar in the heart of Key West's Old Town. Known for his engaging performances…
Free
• February 15, 2026 12:00 pm - 4:45 pm

  John LaMere at Sloppy Joe’s Bar

February 15 @ 12:00 pm - 4:45 pm
John LaMere at Sloppy Joe’s Bar
John LaMere has captivated audiences at Sloppy Joe's Bar since 2011, with his dynamic performances and extensive song list. A weekly fixture on the iconic…
Free
• February 15, 2026 12:00 pm - 5:00 pm

  Mylo O’maolain at Schooner Wharf Bar

February 15 @ 12:00 pm - 5:00 pm
Mylo O’maolain at Schooner Wharf Bar
Experience the captivating sounds of Mylo O'Maolain at Schooner Wharf Bar, a lively open-air venue in Key West. Known for his dynamic performances, Mylo enchants…
Free
• February 15, 2026 12:00 pm - 4:00 pm

  Harley Ray ~ Rick’s Downstairs Stage

February 15 @ 12:00 pm - 4:00 pm
Harley Ray ~ Rick’s Downstairs Stage
Experience the electrifying performance of musician Harley Ray at Rick's Downstairs Stage in Old Town Key West. Known for his dynamic sound and captivating presence,…
Free
• February 15, 2026 2:30 pm - 6:00 pm

  Jeff Harris at Irish Kevin’s Bar

February 15 @ 2:30 pm - 6:00 pm
Jeff Harris at Irish Kevin’s Bar
Experience the dynamic performance of Jeff Harris at Irish Kevin’s Bar in Key West. Known for his engaging live music, Jeff captivates audiences with his…
Free
• February 15, 2026 4:00 pm - 8:00 pm

  Trenton Chandler ~ Rick’s Bar Downstairs Stage

February 15 @ 4:00 pm - 8:00 pm
Trenton Chandler ~ Rick’s Bar Downstairs Stage
Catch Trenton Chandler, a talented country musician and songwriter from Shallowater, Texas, live on the Rick's Bar Downstairs Stage. Influenced by legends like Elvis and…
Free
• February 15, 2026 6:00 pm - 10:00 pm

  Oren Polak at Irish Kevin’s Bar

February 15 @ 6:00 pm - 10:00 pm
Oren Polak at Irish Kevin’s Bar
Oren Polak brings an electrifying energy to Irish Kevin's Bar, a vibrant hotspot in Key West's Old Town known for its nonstop entertainment. As a…
Free
• February 15, 2026 6:30 pm - 10:30 pm

  Meghan Barter at Schooner Wharf Bar

February 15 @ 6:30 pm - 10:30 pm
Meghan Barter at Schooner Wharf Bar
Meghan Barter, a captivating musician, brings her vibrant energy and soulful tunes to the Schooner Wharf Bar in Key West's historic seaport. Her performances at…
Free
• February 15, 2026 7:30 pm - 10:30 pm

  Elle Haley at Tiki House Key West

February 15 @ 7:30 pm - 10:30 pm
Elle Haley at Tiki House Key West
Join the captivating Elle Haley at Tiki House Key West for an unforgettable musical experience. Known for her soulful voice and dynamic performance, Elle brings…
Free
• February 15, 2026 8:00 pm - 11:59 pm

  Aaron Hudgins ~ Rick’s Bar Downstairs Stage

February 15 @ 8:00 pm - 11:59 pm
Aaron Hudgins ~ Rick’s Bar Downstairs Stage
Experience the captivating sounds of Aaron Hudgins at Rick's Bar Downstairs Stage, nestled in Key West's vibrant nightlife hub. Hudgins, a skilled musician, delivers an…
Free
• February 15, 2026 8:00 pm - 11:59 pm

  Sandra Lee at The Bull & Whistle Bar

February 15 @ 8:00 pm - 11:59 pm
Sandra Lee at The Bull & Whistle Bar
Experience the captivating sounds of musician Sandra Lee at The Bull & Whistle Bar. Nestled in Key West's vibrant Old Town, her soulful performances breathe…
Free
• February 15, 2026 9:00 pm - 11:45 pm

  Cliff Cody at Hank’s Hair of the Dog Saloon

February 15 @ 9:00 pm - 11:45 pm
Cliff Cody at Hank’s Hair of the Dog Saloon
Cliff Cody, a captivating musician, graces Hank's Hair of the Dog Saloon in Key West with his soulful tunes and engaging performances. Known for his…
Free