Karaoke with Foss at RockHouse Live
Join Foss for an unforgettable karaoke night at RockHouse Live Key West, where his charisma and engaging presence light up the stage. Experience a lively…
Free
22 events found.
Events for May 29, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Experience the vibrant energy of Karaoke at Bobby's Monkey Bar, where the star is the charismatic karaoke host who engages the lively crowd. Located in…
Riptide Riot at Irish Kevin’s Bar
Riptide Riot, the dynamic power duo from Key West, captivates audiences every week at Irish Kevin's Bar. Featuring Jim Simonian on drums and vocals and…
Free
Yoga on the Beach – Smather’s Beach
Join us for Yoga on the Beach at Smathers Beach in Key West, where our captivating instructor leads rejuvenating sessions set against palm-lined shores and…
$20
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for a daily party boat fishing experience at A & B Marina in Key West's historic seaport. Enjoy live entertainment amidst the…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Join Yoga on the Beach at Fort Zachary Taylor in Key West, where the serene surroundings enhance your practice. With a focus on relaxation and…
$20
Story Time at the Key West Library
Experience enchanting tales at Story Time at the Key West Library, where a captivating storyteller brings each narrative to life. Nestled in the historic Old…
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 group of four. The entertainer, a spirited mixologist, will guide you through…
$75.00
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant Key West Legal Rum Distillery with daily free tours and tastings. Although there’s no specific entertainer mentioned, the lively setting itself offers…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise for a unique maritime experience in Key West. While the tour offers breathtaking views of vibrant marine life through…
$69.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the vibrant marine life of Key West aboard the Glass Bottom Boat Cruise, featuring captivating performances by talented local entertainers. This unique excursion combines…
$69.95
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 the vibrant Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports in Key West's Historic Seaport. Dive into an adventure with…
$79.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West, where the ocean comes alive beneath your feet. Marvel at the vibrant marine life through…
$69.95
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls deliver an unforgettable drag experience in their 5pm show at 801 Bourbon Bar, Key West. Renowned for their vibrant performances…
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a lively spectacle where talented entertainers captivate audiences as the sun dips below the horizon.…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West enchants audiences at El Meson de Pepes on Mallory Square with captivating live music that echoes the rich Cuban-Conch heritage of…
Trae Pierce & The T-Stones at Green Parrot Bar
Experience the electrifying energy of Trae Pierce & The T-Stones at the Green Parrot Bar. Led by 4-time Grammy Award winner Trae Pierce, this dynamic…
Free
Karaoke at Two Friends Patio
Experience lively karaoke nights at Two Friends Patio, a Key West favorite since 1967. The enchanting open-air setting comes alive with charismatic entertainers, making each…
Free
Trae Pierce & The T-Stones at Green Parrot Bar
Experience the electrifying performance of Trae Pierce & The T-Stones at the Green Parrot Bar. Led by four-time Grammy winner Trae Pierce, this dynamic band…
Free
Karaoke at Bobby’s Monkey Bar
Join the lively atmosphere at Bobby's Monkey Bar for an unforgettable Karaoke night. The highlight of the evening is the charismatic entertainer who engages the…
Trae Pierce & The T-Stones at Green Parrot Bar
Experience the electrifying rhythm of Trae Pierce & The T-Stones at Green Parrot Bar. Led by four-time Grammy winner Trae Pierce, the band is celebrated…
Free