Izzy Zaidman at Sloppy Joe’s Bar
Experience the captivating performance of Izzy Zaidman at Sloppy Joe's Bar in Key West. As a talented musician, guitarist, composer, and singer-songwriter, Izzy enchants audiences…
Free
47 events found.
Events for July 15, 2026
Sharese at Rams Head Southernmost
Experience the soulful tunes of Sharese Nicole at Rams Head Southernmost, where her Mississippi and Key West roots shine through her music. Known for her…
Free
Oren Polak at Irish Kevin’s Bar
At Irish Kevin's Bar, Oren Polak delivers captivating performances that engage audiences with his talent and charisma. As a versatile musician and band leader, he…
Free
Carson Lowe at Rick’s Downstairs Stage
Carson Lowe captivates audiences at Rick's Downstairs Stage with his dynamic performances and engaging presence. Known for his soulful melodies and vibrant energy, he transforms…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant nightlife atmosphere at Key West First Legal Rum Distillery in the Historic Seaport. Enjoy daily free tours, rum samples, and mojito-making classes.…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery, where a charismatic entertainer guides you through the art of crafting the perfect mojito. Set…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Explore the vibrant marine life of the Florida Keys on the Glass Bottom Boat Cruise, departing from Fury Key West. This captivating experience promises unforgettable…
$69.95
Andy Mauerman at Hog’s Breath Saloon
Andy Mauerman captivates audiences at Hog's Breath Saloon with his vibrant music and magnetic presence. As a musician and advocate for experiential living, Andy inspires…
Free
Wednesday Filet Day at Mary Ellen’s
Mary Ellen's Wednesday Filet Day is a must-visit in Old Town Key West, where the lively atmosphere pairs perfectly with live music from talented local…
Free
Brian Roberts at Sloppy Joe’s Bar
Brian Roberts, a captivating singer/songwriter from the Florida Keys, energizes audiences at Sloppy Joe's Bar. Performing live every Tuesday and Wednesday afternoon, he brings a…
Free
Caffeine Carl Memorial at The Key West Theatre
Caffeine Carl Memorial at the Key West Theatre
Sharese Nicole at Tiki House Key West
Sharese Nicole is a captivating singer and songwriter performing at Tiki House Key West. With roots in Mississippi and Key West, she embodies her philosophy…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the mesmerizing Glass Bottom Boat Cruise in Key West, featuring a captivating entertainer who brings the marine wonders to life. Depart from Fury Key…
$69.95
Alfonse at Two Friends Patio Restaurant
Alfonse, a talented musician, enchants guests at Two Friends Patio Restaurant in Key West with his captivating performances. Amid the vibrant atmosphere of this iconic…
Free
Aaron Hudgins at Irish Kevin’s Bar
Aaron Hudgins electrifies the crowd at Irish Kevin's Bar with his dynamic performances. As a talented musician, he captivates audiences with his engaging stage presence…
Free
Chris M at Two Friends Patio Restaurant
Chris M captivates audiences at Two Friends Patio Restaurant with his dynamic live performances. Situated in the heart of Key West, this lively venue enhances…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience the ultimate aquatic adventure with Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports, Key West. Guided by skilled entertainers, explore…
$79.95
Harley Ray at Rick’s Bar Downstairs Stage
Harley Ray captivates audiences at Rick's Bar Downstairs Stage with his heartfelt and innovative songwriting. His melodies and lyrics resonate on a deeply personal level,…
Free
Just George at Old Sailor Bar
Experience the soul-stirring acoustic melodies of Just George at Old Sailor Bar, a cornerstone of Key West's nightlife. This passionate musician enchants audiences with his…
Free
Shastina Chiles at Hank’s Hair of the Dog Saloon
Catch the electrifying performance of Shastina Chiles at Hank's Hair of the Dog Saloon in Key West's vibrant Old Town. Known for her captivating presence…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise from Key West with a stellar entertainer elevating the journey. Enjoy captivating commentary and lively performances as you…
$69.95
Tim & Teague at Hog’s Breath Saloon
Step into the vibrant atmosphere of Hog's Breath Saloon and let Tim & Teague captivate you with their live music performance. Known for their engaging…
Free
World Famous 801 Girls- 5pm Show
Experience the vibrant energy of the World Famous 801 Girls at their 5pm show in Old Town Key West's iconic 801 Bourbon Bar. These talented…
Dallas Reminton at Mac’s Place
Dallas Remington, a vibrant country music artist, performs at Mac's Place. Known for her blend of class and sass, she captivates audiences with her passionate…
Free
Tony Roberts at Sunset Tiki Bar & Grill
Tony Roberts, a talented Key West singer-songwriter, captivates audiences at Sunset Tiki Bar & Grill with his soulful guitar performances. Known for his thick beard…
Free
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where entertainment takes center stage. Revel in the captivating performances of street entertainers like jugglers and the…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant sounds of Caribe of Key West at El Meson de Pepes on Mallory Square. This family-owned Cuban restaurant enchants guests with live…
Cayo Ritmo at Green Parrot Bar
Experience the vibrant sounds of Cayo Ritmo at the iconic Green Parrot Bar in Key West. Known for their energetic performances, Cayo Ritmo brings a…
Free
Victoria Leigh at Sloppy Joe’s Bar
Victoria Leigh, a dynamic musician from the Florida Keys, lights up Sloppy Joe's Bar with her electrifying performances. Known for her feel-good covers and original…
Free
John Sausser at Rams Head Southernmost
Experience the captivating performance of John Sausser at Rams Head Southernmost, where his musical talents shine amidst a lively island atmosphere. Enjoy his dynamic live…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a charismatic entertainer at Irish Kevin's Bar, renowned for his humor and captivating performances. Known for his genuine and fun-loving spirit, he…
Free
Line Dancing at Kaya Island Eats
Kick up your heels at Kaya Island Eats for an unforgettable evening of line dancing. Nestled in Key West, this laid-back venue blends Caribbean culinary…
Free
Ericson Holt at Two Friends Patio Restaurant
Experience the captivating sounds of musician Ericson Holt at Two Friends Patio Restaurant. Known for his soulful performances, Ericson brings a unique blend of blues…
Free
Irie Monte at ViV Wine & Cheese Bar Key West
Experience the captivating melodies of Irie Monte at ViV Wine & Cheese Bar in Key West. Located in Bahama Village near Duval Street, this venue…
Free
Andrew B. at Rick’s Bar Downstairs Stage
Andrew Burleson graces Rick's Bar Downstairs Stage with his captivating melodies and charming humor. Known for his engaging performances, Andrew often lightens the atmosphere with…
Free
DJ Todd at Red Garter Saloon Stage
Experience the electrifying energy of DJ Todd at the Red Garter Saloon Stage. Renowned for his innovative mixes and dynamic performances, DJ Todd captivates audiences…
Free
Aaron Hudgins at Hank’s Hair of the Dog Saloon
Aaron Hudgins captivates audiences at Hank's Hair of the Dog Saloon with his dynamic musical performances. Known for his engaging presence and versatile style, he's…
Free
Karaoke at Kaya Island Eats
Experience an unforgettable night at Kaya Island Eats with captivating karaoke entertainment. The talented entertainer will energize the crowd, encouraging both seasoned singers and enthusiastic…
DJ Duke at Rick’s Bar Upstairs Stage
DJ Duke, a dynamic and innovative music producer, takes center stage at Rick's Bar Upstairs Stage. Known for his mesmerizing mixes and electrifying performances, he…
Free
Daniel Lynn Band at Hog’s Breath Saloon
Experience the electrifying performance of Daniel Lynn Band at Hog's Breath Saloon. Known for their dynamic sound and engaging stage presence, the band creates an…
Free
Crank Sinatra at Durty Harry’s Stage
Experience the dynamic energy of Krank Sinatra at Durty Harry's Stage. Known as a talented vocalist, guitarist, and songwriter, he captivates audiences with electrifying performances.…
Free
Cayo Ritmo at Green Parrot Bar
Experience the infectious energy of Cayo Ritmo at the iconic Green Parrot Bar in Key West. This dynamic band brings a vibrant mix of rhythms…
Free
Karaoke at Bobby’s Monkey Bar
Enjoy a vibrant night of music at Bobby's Monkey Bar in Key West's Old Town. Experience the lively island atmosphere as entertainers bring the karaoke…
Kari Wolf at Irish Kevin’s Bar
Kari Wolf captivates audiences at Irish Kevin's Bar in Key West with her dynamic performances and soulful melodies. This talented musician brings a unique style…
Free
King Pin at Sloppy Joe’s Bar
King Pin electrifies the stage at Sloppy Joe's Bar, captivating audiences with his dynamic performance and charisma. Known for his engaging presence and musical prowess,…
Free
Cayo Ritmo at Green Parrot Bar
Cayo Ritmo brings electrifying energy to the iconic Green Parrot Bar in Key West. Renowned for their vibrant performances, this band infuses the historic dive…
Free
Karaoke w/ Davis at Rick’s Bar Downstairs Stage
Join DJ Davis at Rick's Bar Downstairs Stage for an electrifying karaoke night. Renowned for his eclectic beats and infectious energy, Davis expertly reads the…
Free