Martini Monday at Virgilios
Experience the captivating sounds of talented musicians at Martini Monday at Virgilio's in Old Town Key West. This stylish cocktail lounge offers an impressive martini…
Free
23 events found.
Events for May 26, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Join the vibrant atmosphere at Bobby's Monkey Bar for an unforgettable karaoke night. The entertainer takes center stage, captivating the crowd with charisma and energy,…
Mylo O’Maolain at Irish Kevin’s Bar
Experience the energetic performance of Mylo O'Maolain at Irish Kevin's Bar, where his captivating act lights up the stage. Known for engaging his audience with…
Free
Ambitious Morning Runners
Join the Ambitious Morning Runners at White Street Pier in Key West, a stunning oceanfront location famous for its breathtaking sunset views and peaceful ambiance.…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max for a memorable daily party boat fishing adventure departing from A & B Marina in Key West's historic seaport. Experience lively…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join Yoga on the Beach at Fort Zachary Taylor State Park for a rejuvenating session that combines tranquility with stunning views. This event offers a…
$20
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, an enriching experience set against the serene backdrop of the Key West Tropical Forest & Botanical Garden.…
$20
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga, an enriching experience set against the serene backdrop of the Key West Tropical Forest & Botanical Garden.…
$20
Bradd Shadduck at Irish Kevin’s Bar
At Irish Kevin’s Bar, Bradd Shadduck energizes the crowd with his dynamic musical performances, making every night unforgettable in the heart of Old Town Key…
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
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
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a laid-back and fun-loving entertainer at Irish Kevin's Bar in Key West. Known for his charm and humor, he captivates audiences with…
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
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
World Famous 801 Girls- 5pm Show
Experience the dazzling charisma of the World Famous 801 Girls at their 5pm show. These talented drag queens captivate audiences with their vibrant performances at…
Sunset Celebration at Mallory Square
Experience the Sunset Celebration at Mallory Square, where the captivating entertainer, the famous cat man, mesmerizes audiences with his unique feline performances. As the sun…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant atmosphere at El Meson de Pepes on Mallory Square, where Caribe of Key West brings lively performances that captivate audiences. Savor authentic…
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin's Bar in Key West, captivating audiences with his vibrant and seamless blend of music and entertainment.…
Free
Comedy Key West Open Mic at Comedy Key West
Join Comedy Key West's Open Mic Night for an electrifying evening filled with laughter and creativity. Perfect for budding comedians or seasoned performers, this event…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant atmosphere at Bobby's Monkey Bar in Key West for an unforgettable evening of karaoke. Enjoy captivating performances by talented entertainers as they…
Simonian Wolf at Irish Kevin’s Bar
Simonian Wolf brings an electrifying presence to Irish Kevin’s Bar in Key West. Known for their charisma and innovative flair, Wolf captivates audiences through an…
Free