Karaoke with Foss at RockHouse Live
Join Foss for an unforgettable karaoke night at RockHouse Live, Key West. Known for his electrifying presence and talent, Foss elevates the evening with engaging…
Free
27 events found.
Events for May 22, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Join the vibrant nightlife at Bobby's Monkey Bar in Old Town Key West, where the standout entertainer takes the stage for an unforgettable karaoke experience.…
Riptide Riot at Irish Kevin’s Bar
Riptide Riot, a dynamic power duo hailing from Key West, electrifies audiences at Irish Kevin's Bar. Featuring Jim Simonian on drums and vocals and Tim…
Free
Yoga on the Beach – Smather’s Beach
Join a rejuvenating Yoga on the Beach session at Smather's Beach with renowned instructor Maya Soleil. Embrace the serene surroundings of Key West's palm-lined shores…
$20
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max for a daily party boat fishing adventure at A & B Marina in Key West. While the marina offers excellent boating…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join a rejuvenating Yoga on the Beach at Fort Zachary Taylor in Key West. As you stretch and unwind, be captivated by the scenic beauty…
$20
Story Time at the Key West Library
Experience the enchanting world of stories with renowned storyteller, captivating audiences of all ages at the Key West Library. Nestled in Old Town, this engaging…
Free
Jeff Harris at Irish Kevin’s Bar
Jeff Harris, a multi-talented performer, lights up Irish Kevin's Bar with his captivating blend of music and comedy. As a singer-songwriter and comedian, he effortlessly…
Free
Distillery Tour – Key West Legal Rum Distillery
Explore the captivating Key West Legal Rum Distillery located in the Historic Seaport, offering an engaging atmosphere with daily free tours and tastings. Delight in…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at the Key West Legal Rum Distillery, where a talented entertainer guides you through the art of crafting the perfect mojito.…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for a captivating evening of ocean exploration. Highlighting a talented entertainer, the cruise combines marine beauty…
$69.95
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Join acclaimed musician, actor, and Buffett historian Caleb Hogan at Comedy Key West for A Pirate Looks Back: Jimmy Buffett Tribute Show. Experience a captivating…
$28
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for an unforgettable journey with spectacular views of marine life. The highlight of the cruise is…
$69.95
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain is a dynamic entertainer performing at Irish Kevin's Bar in Key West. Known for captivating audiences with his lively performances, Mylo brings energy…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for a thrilling daily party boat fishing adventure at A & B Marina in Key West's historic seaport. While enjoying the vibrant…
$85.00
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience an unforgettable aquatic adventure with Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports in Key West. Dive into vibrant coral…
$79.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West and enjoy the mesmerizing views of the ocean beneath you, all while being entertained by talented…
$69.95
World Famous 801 Girls- 5pm Show
Experience the dazzling World Famous 801 Girls at their 5pm show, where their charismatic performances light up the stage. Set in the lively 801 Bourbon…
Sunset Celebration at Mallory Square
Experience the enchanting Sunset Celebration at Mallory Square, a Key West hotspot where entertainment meets breathtaking ocean views. Be mesmerized by talented street performers, including…
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 essence of Cuban…
The Resolvers at Green Parrot Bar
The Resolvers, Florida's premier reggae band, will take the stage at Green Parrot Bar, renowned for its vibrant live music scene. Fusing big band reggae…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin's Bar in Key West, Florida. Renowned for his captivating shows, he effortlessly blends music and entertainment,…
Free
Karaoke at Two Friends Patio
Join the lively atmosphere at Two Friends Patio, where the real star is the charismatic karaoke host. Enjoy an unforgettable night of entertainment as the…
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
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…
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
The Resolvers at Green Parrot Bar
Florida's biggest reggae band, The Resolvers, bring their vibrant fusion of big band reggae and energetic rhythms to the Green Parrot Bar. Known for their…
Free