DJ Todd ~ Red Garter Saloon at Rick’s Entertainment Complex
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…
Free
24 events found.
Events for January 16, 2026
Ongoing
KRANK SINATRA~ Durty Harry’s Stage at Rick’s Entertainment Complex
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,…
Free
DJ Duke ~ Rick’s Bar Upstairs at Rick’s Entertainment Complex
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…
Free
Karaoke w/ Davis ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
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…
Free
Rolando Rojas at Sloppy Joe’s Bar
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…
Free
Wynn Tayor ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
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,…
Free
Tim Hollohan at Sloppy Joe’s Bar
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…
Free
Tony Baltimore at Schooner Wharf Bar
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…
Free
Burgers & Buffett Tunes at Comedy Key West
Step into the vibrant world of Caleb Hogan, an acclaimed musician, actor, and Buffett historian, at Comedy Key West's Burgers & Buffett Tunes. Hogan channels…
$28
Joe the Show ~ Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex
Experience the electrifying talent of Joe the Show at Rick's Bar Downstairs Stage in Key West. Known for his dynamic performances, Joe delivers a captivating…
Free
Hemingway in a Funny Way at Comedy Key West
Join stand-up comedian James Scott Patterson at Comedy Key West for a hilarious romp through Ernest Hemingway's life. Known for his Comedy Central appearances and…
$28
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Experience an unforgettable evening with Pete & Larry, the dynamic duo known as Sloppy 2nds, at Sloppy Joe's Bar. Renowned for their infectious energy and…
Free
DALLAS REMINGTON ~ Durty Harry’s Stage at Rick’s Entertainment Complex
Experience the dynamic performance of musician Dallas Remington on Durty Harry's Stage at Rick's Entertainment Complex. With his compelling presence and captivating music, Dallas brings…
Free
Dave Richards Band at Schooner Wharf Bar
Experience the captivating sounds of the Dave Richards Band at the Schooner Wharf Bar in Key West. Known for their lively performances and dynamic musical…
Free
Joe the Show ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Experience an unforgettable night with Joe the Show at Rick's Bar, tucked away in Rick's Entertainment Complex. Joe captivates audiences with his dynamic performances in…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the mesmerizing Magic of Frank Everhart at the Schooner Wharf Bar, Key West's beloved open-air venue. Renowned magician Frank Everhart captivates audiences with his…
Free
DJ Marty ~ Red Garter Saloon at Rick’s Entertainment Complex
Join DJ Marty at the Red Garter Saloon in Rick's Entertainment Complex for an electrifying night in Key West's vibrant nightlife scene. Known for his…
Free
Kash’d Out With Seranation at Key West Theater
Experience the energetic vibes of Kash'd Out, a standout band known for their infectious reggae-rock fusion, at the historic Key West Theater. Enjoy an unforgettable…
$
Jimmy Buffett’s Coral Reefer Band at Key West Theater
Join Jimmy Buffett's legendary Coral Reefer Band for an unforgettable performance at the historic Key West Theater. Immerse yourself in the laid-back charm and tropical…
$
Brendan Sagalow at Comedy Key West
New York City-based comedian Brendan Sagalow brings his sharp wit and confident social observations to Comedy Key West. Celebrated for his blend of self-deprecation and…
$30
DURTBAGS~ Durty Harry’s Stage at Rick’s Entertainment Complex
Experience the electrifying energy of The Durtbags, Key West’s premier party rock band, live at Durty Harry's Stage within Rick's Entertainment Complex. Every Thursday through…
Free
DJ Chaka ~ Rick’s Bar Upstairs at Rick’s Entertainment Complex
Experience the electrifying beats of DJ Chaka at Rick's Bar, located upstairs at Rick's Entertainment Complex in Key West. Renowned for his dynamic sets and…
Free
Super Nash Bros at Sloppy Joe’s Bar
Catch the electrifying Super Nash Bros performing at Sloppy Joe's Bar, a legendary Key West spot since 1937. Feel the energy as this dynamic duo…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs at Rick’s Entertainment Complex
Join Jason for an unforgettable night of karaoke at Rick's Bar, located downstairs at Rick's Entertainment Complex in Key West. Known for his engaging style…
Free