Karaoke at Bobby’s Monkey Bar
Experience lively karaoke nights at Bobby's Monkey Bar in Key West's Old Town. Although specific entertainer details are not available, the vibrant island atmosphere and…
25 events found.
Events for May 23, 2026
Ongoing
Riptide Riot at Irish Kevin’s Bar
Riptide Riot, a dynamic power duo from Key West, electrifies audiences weekly at Irish Kevin's Bar. With Jim Simonian on drums and vocals and Tim…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing adventure at A & B Marina in Key West's historic seaport. Enjoy a vibrant atmosphere with live…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Experience tranquility with Yoga on the Beach at Fort Zachary Taylor in Key West. While the park's stunning seascapes and rich Civil War history set…
$20
Prime of Life Yoga with Monica Haskell
Experience rejuvenation with Monica Haskell at Prime of Life Yoga, set amidst the enchanting Key West Tropical Forest & Botanical Garden. Monica, a seasoned yoga…
$20
Jeff Harris at Irish Kevin’s Bar
At Irish Kevin’s Bar in Key West, Jeff Harris captivates audiences with his multi-talented artistry. An American singer, songwriter, and comedian, Jeff blends music and…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant nightlife atmosphere at Key West First Legal Rum Distillery. Enjoy free daily tours and tastings in this historic seaport location, once a…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West Legal Rum Distillery with a minimum of four people for an unforgettable experience. Enjoy lively entertainment as expert…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the Glass Bottom Boat Cruise in Key West, where a charming entertainer guides you through the vibrant marine life visible beneath your feet. With…
$69.95
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Caleb Hogan shines as Jimmy Buffett in A Pirate Looks Back, delivering an engaging tribute to the legendary musician. With charm and authenticity, Hogan encapsulates…
$28
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West where the stars of the show are the vibrant marine life visible through the crystal-clear…
$69.95
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin's Bar in Key West, Florida. Known for his captivating performances that seamlessly blend music and entertainment,…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for daily party boat fishing at A & B Marina in Key West's historic seaport. Enjoy the beautiful waterfront and lively atmosphere,…
$85.00
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join Sunset Watersports in Key West's Historic Seaport for an unforgettable adventure. Although details about the entertainer are sparse, the experienced staff ensures a thrilling…
$79.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join us for the Glass Bottom Boat Cruise in Key West, a unique journey showcasing the magical underwater world. Delight in live entertainment that enhances…
$69.95
World Famous 801 Girls- 5pm Show
Experience the dazzling performances of the World Famous 801 Girls at their 5pm show, held at the vibrant 801 Bourbon Bar in Key West. Known…
Sunset Celebration at Mallory Square
Experience the Sunset Celebration at Mallory Square, where performers captivate with breathtaking acts. From daring jugglers to the enchanting antics of the famous cat man,…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant rhythms of Caribe of Key West at El Meson de Pepes on Mallory Square. This talented entertainer brings the lively spirit of…
The Resolvers at Green Parrot Bar
Experience The Resolvers at Green Parrot Bar, where Florida's biggest reggae band brings the house down with their vibrant fusion of big band reggae and…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a charismatic and jovial entertainer at Irish Kevin's Bar in Key West, known for his charm and humor. His engaging performances, featuring…
Free
Karaoke at Two Friends Patio
Experience lively karaoke at Two Friends Patio, a beloved Key West destination. The highlight of the event is the charismatic entertainer who engages and energizes…
Free
The Resolvers at Green Parrot Bar
The Resolvers, Florida's premier reggae band, bring their dynamic fusion of big band reggae and energetic rhythms to the iconic Green Parrot Bar. Known for…
Free
Karaoke at Bobby’s Monkey Bar
Experience an unforgettable night of karaoke at Bobby's Monkey Bar, where the star of the show is the charismatic karaoke host. With their vibrant energy…
Jack and Jim Show at Irish Kevin’s Bar
Experience the electrifying Jack and Jim Show at Irish Kevin's Bar, where these dynamic entertainers captivate audiences with their energetic performances. Set in the lively…
Free
The Resolvers at Green Parrot Bar
The Resolvers, Florida's premier reggae band, bring their vibrant fusion of big band reggae and energetic rhythms to the Green Parrot Bar. Known for their…
Free