Joe the Show ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-14 19:00 - 23:00 (America/New_York)
Experience the unforgettable talent of Joe the Show at Rick’s Bar, nestled within Key West’s renowned Rick’s Entertainment Complex. This gifted musician captivates audiences with electrifying performances, making every night memorable. Dive into the vibrant nightlife, enjoy diverse music, and savor the energetic atmosphere. A can’t-miss event for music lovers!

Magic Of Frank Everhart at Schooner Wharf Bar
2026-01-14 19:00 - 23:59
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West’s Seaport. Frank Everhart captivates audiences with mesmerizing magic and unforgettable performances in a laid-back, open-air setting. Enjoy fresh seafood, stunning dockside views, and the unique charm of this historic bar as Frank’s spellbinding artistry adds a touch of magic to your evening.

DJ Todd ~ Red Garter Saloon at Rick's Entertainment Complex
2026-01-14 19:00 - 2026-01-15 04:00
Experience the electrifying beats of DJ Todd at the Red Garter Saloon in Rick’s Entertainment Complex, Key West’s nightlife hub. Known for his dynamic energy and impeccable mixing skills, DJ Todd creates an unforgettable atmosphere, perfect for dancing the night away. Join the excitement in Old Town’s largest club and enjoy vibrant entertainment.

The Expanding Man at Key West Theater
2026-01-14 20:00 - 22:00
Experience the dynamic sounds of The Expanding Man at the historic Key West Theater. This band offers an exhilarating performance that captivates audiences with their unique musical flair. Set in the intimate ambiance of a newly renovated venue, this event promises an unforgettable evening of top-tier entertainment in the heart of Old Town.

Hard G Comedy W/ Robyn and Jason Gilleran at Comedy Key West
2026-01-14 20:30 - 22:30
Join us for Hard G Comedy at Comedy Key West, featuring the dynamic duo Robyn and Jason Gilleran. Detroit-based comedian Robyn Gilleran captivates audiences with her sharp wit on motherhood and life, while Jason, a fixture in the Detroit comedy scene, complements the act. Together, they deliver memorable laughs and entertainment.

LUVBOM ~ Durty Harry's Stage at Rick's Entertainment Complex
2026-01-14 21:00 - 2026-01-15 02:00
Experience the electrifying energy of LUVBOM at Durty Harry’s Stage in Rick’s Entertainment Complex. Nestled in the heart of Old Town Key West, LUVBOM captivates audiences with their dynamic rock performances. Their exhilarating music creates an unforgettable atmosphere, ensuring a memorable night out in the largest club south of Miami, amid vibrant nightlife and endless fun.

DJ Duke ~ Rick's Bar Upstairs at Rick's Entertainment Complex
2026-01-14 21:00 - 2026-01-15 04:00
Experience DJ Duke’s electrifying beats at Rick’s Bar, located upstairs at Rick’s Entertainment Complex. Renowned for his captivating sets, DJ Duke transforms the night into an unforgettable musical journey. Dive into Key West’s largest club scene as his rhythms pulse through the vibrant atmosphere, drawing you into a world of dance and celebration.

Super Nash Bros at Sloppy Joe's Bar
2026-01-14 22:00 - 23:59
Experience an unforgettable night with the Super Nash Bros at Sloppy Joe’s Bar, Key West’s historic landmark since 1937. Renowned for their electrifying performances and dynamic sound, Super Nash Bros promise a lively evening filled with great music, blending seamlessly with the bar’s vibrant atmosphere and rich history on Duval Street.

Karaoke w/ Jorge ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-14 23:00 - 2026-01-15 04:00
Join Jorge for an unforgettable karaoke night at Rick’s Bar, located in the vibrant Rick’s Entertainment Complex, Key West. As a charismatic entertainer, Jorge captivates with his infectious energy, turning each session into a must-see event. Sing your heart out and enjoy a lively atmosphere, perfect for music lovers and partygoers alike.

Izzy Zaidman at Sloppy Joe's Bar
2026-01-15 10:00 - 11:45
Izzy Zaidman, a gifted musician, has captivated Key West since his arrival in 2021. With his Steel Resonator guitar, he brings the vibrant sounds of American Roots music to life at Sloppy Joe’s Bar. His performances are a must-see, making the historic venue pulse with energy and authentic charm.

Sid The Bayou Kid at Sloppy Joe's Bar
2026-01-15 12:00 - 16:45
Sid The Bayou Kid brings his unique swampy sound to Sloppy Joe’s Bar, a historic venue in Key West. With over 30 years of experience performing across the country, Sid captivates audiences with his lively music infused with the soulful essence of Thibodaux, LA. Enjoy an unforgettable performance in a vibrant atmosphere.

Ross Brown at Schooner Wharf Bar
2026-01-15 12:00 - 17:00
Ross Brown, a talented musician, brings his captivating performances to the lively Schooner Wharf Bar in Key West. Known for his engaging stage presence and musical prowess, Ross entertains locals and visitors alike in this laid-back, open-air venue. Enjoy unforgettable tunes alongside stunning dockside views and fresh seafood delights.

Burgers & Buffett Tunes at Comedy Key West
2026-01-15 12:30 - 14:30
Experience a captivating lunchtime tribute at Comedy Key West with acclaimed musician and Buffett historian Caleb Hogan. Dressed as Jimmy Buffett, Hogan delivers an unforgettable performance blending live music, storytelling, and humor. Relive the 1970s Key West era with this unique musical celebration of Buffett’s legacy, complete with cheeseburgers and classic tunes.

Jeff Harris ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-15 15:00 - 19:00
Experience the electrifying performance of musician Jeff Harris at Rick’s Bar, located in the renowned Rick’s Entertainment Complex in Old Town Key West. Known for his captivating live shows and extraordinary musical talent, Jeff elevates the vibrant nightlife with his dynamic presence, making it a must-visit for music lovers and revelers alike.

Pete & Larry Sloppy 2nds at Sloppy Joe's Bar
2026-01-15 17:30 - 21:30
Experience the infectious energy of Pete & Larry, known as Sloppy 2nds at the iconic Sloppy Joe’s Bar. This dynamic duo delivers uproarious comedy and spirited sing-alongs, ensuring a night of non-stop entertainment. With their engaging performances, they transform any evening into a memorable celebration of music and laughter.

Nick Brownwell at Schooner Wharf Bar
2026-01-15 18:30 - 22:30
Experience the musical talents of Nick Brownell at the iconic Schooner Wharf Bar. Known for his engaging performances, Nick brings energy and charisma to Key West’s beloved waterfront venue. As he captivates audiences with his vibrant tunes, enjoy the laid-back atmosphere, fresh seafood, and unforgettable sailing tales under the stunning dockside views.

Scott Kirby With Caffeine Carl at Key West Theater
2026-01-15 19:00 - 21:00
Experience an unforgettable evening with renowned entertainer Scott Kirby, accompanied by the dynamic Caffeine Carl, at the historic Key West Theater. Known for his captivating performances and masterful storytelling through music, Scott Kirby promises an intimate and engaging show in this charming, newly renovated venue in the heart of Old Town Key West.

Andrew B. ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-15 19:00 - 23:00
Experience an electrifying evening with Andrew B., the captivating musician at Rick’s Bar, nestled in the bustling heart of Old Town Key West. Known for his dynamic performances, Andrew brings energy and flair to the largest club south of Miami. Enjoy his live music amidst vibrant nightlife and endless fun.

Magic Of Frank Everhart at Schooner Wharf Bar
2026-01-15 19:00 - 23:59
Experience the mesmerizing Magic of Frank Everhart at the Schooner Wharf Bar, a Key West icon. Frank’s enchanting performances captivate audiences against a backdrop of stunning dockside views. As a renowned magician, his spellbinding tricks and engaging presence elevate the vibrant atmosphere, making every visit unforgettable in this historic, open-air waterfront setting.

DJ Todd ~ Red Garter Saloon at Rick's Entertainment Complex
2026-01-15 19:00 - 2026-01-16 04:00
DJ Todd brings electrifying energy to the Red Garter Saloon at Rick’s Entertainment Complex, transforming it into the ultimate nightlife destination in Key West. Known for his dynamic mixes and unbeatable beats, DJ Todd ensures every night is unforgettable. Dance the night away and enjoy his unmatched talent in this vibrant setting.

Asleep At The Wheel at Key West Theater
2026-01-15 20:00 - 22:00
Experience the legendary Asleep At The Wheel at Key West Theater, an intimate historic venue in Old Town. Renowned for their exceptional musicianship and dedication to the classic sounds of Western swing, Asleep At The Wheel brings a captivating and energetic performance that celebrates the rich tradition of American roots music.

Brendan Sagalow at Comedy Key West
2026-01-15 20:30 - 22:30
Brendan Sagalow, a seasoned New York City-based comedian, brings his unique blend of confident social observation and sharp self-deprecation to Comedy Key West. With over a decade of experience, Sagalow has captivated audiences nationwide. His debut special, Thin Lips, is celebrated on YouTube, and his festival appearances and podcast features showcase his comedic prowess.

KRANK SINATRA~ Durty Harry's Stage at Rick's Entertainment Complex
2026-01-15 21:00 - 2026-01-16 02:00
Experience the electrifying performance of Krank Sinatra at Durty Harry’s Stage within Rick’s Entertainment Complex. Renowned for their dynamic rock sound and engaging stage presence, Krank Sinatra captivates audiences in Key West’s largest nightlife venue. Dance the night away to their incredible live music, complemented by vibrant bars and an unforgettable atmosphere.

DJ Duke ~ Rick's Bar Upstairs at Rick's Entertainment Complex
2026-01-15 21:00 - 2026-01-16 04:00
Experience the electrifying beats of DJ Duke at Rick’s Bar, located in Rick’s Entertainment Complex, Old Town Key West. Renowned for his dynamic mixes and vibrant energy, DJ Duke transforms the venue into a pulsating dance haven. Enjoy an unforgettable night of music and entertainment in Key West’s largest and most iconic nightlife spot.

Super Nash Bros at Sloppy Joe's Bar
2026-01-15 22:00 - 23:59
Experience the vibrant tunes of Super Nash Bros at Sloppy Joe’s Bar, a historic Key West gem. Nestled on Duval Street, this iconic venue promises an unforgettable evening filled with electrifying live music. Enjoy delicious American cuisine and classic cocktails as the Super Nash Bros captivate you with their energetic performance in this lively setting.

Karaoke w/ Davis ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-15 23:00 - 2026-01-16 04:00
Join Davis for an unforgettable karaoke experience at Rick’s Bar, nestled within Key West’s premier entertainment hub. With his engaging personality and musical prowess, Davis turns every night into a lively sing-along. Dive into endless fun and let Davis elevate your night at Rick’s Entertainment Complex’s most vibrant spot.

Rolando Rojas at Sloppy Joe's Bar
2026-01-16 10:00 - 11:45
Witness the electrifying performance of Rolando Rojas at Sloppy Joe’s Bar, a historic Key West landmark. Renowned for his charismatic stage presence and exceptional guitar skills, Rojas captivates audiences with every note. Don’t miss the chance to experience one of Key West’s most sought-after wedding acts in this lively, iconic setting.

Wynn Tayor ~ Rick's Bar Downstairs Stage at Rick's Entertainment Complex
2026-01-16 12:00 - 16:00
Experience the dynamic performance of musician Wynn Taylor on the Downstairs Stage at Rick’s Bar in Rick’s Entertainment Complex. Renowned for his captivating live shows, Taylor brings an electric energy to Key West’s vibrant nightlife scene. Don’t miss the opportunity to enjoy his music amidst eight iconic bars in Old Town’s largest club.

Tim Hollohan at Sloppy Joe's Bar
2026-01-16 12:00 - 16:45
Tim Hollohan captivates audiences at Sloppy Joe’s Bar in Key West with his engaging performances and interactive stage presence. Originally from Columbia, South Carolina, Tim brings his musical talents to this historic venue almost daily, enhancing the lively atmosphere with his charismatic flair and compelling music, making each visit memorable.

Tony Baltimore at Schooner Wharf Bar
2026-01-16 12:00 - 17:00
Tony Baltimore brings his captivating musical talents to the Schooner Wharf Bar, a beloved local venue in Key West. With a mix of soulful melodies and vibrant rhythms, Tony’s performances perfectly complement the bar’s laid-back, open-air ambiance. Enjoy an unforgettable evening of live music against stunning dockside views and island cuisine delights.
