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…
24 events found.
Events for May 24, 2026
Ongoing
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
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 State Park. This unique event combines the serene beauty of a historic beachside setting with invigorating…
$20
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck captivates audiences at Irish Kevin's Bar with his dynamic musical performances. Nestled in Old Town Key West, this lively venue on Duval Street…
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
Farm Open House
Experience a delightful afternoon at the Farm Open House, where family fun meets education at this nonprofit sanctuary. Highlighted by an engaging entertainer, the event…
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
Jeff Harris at Irish Kevin’s Bar
Experience the multifaceted talents of Jeff Harris at Irish Kevin's Bar, where he enthralls audiences with his unique blend of music and comedy. As a…
Free
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
Tea Dance at La Te Da
Experience the exuberance of Tea Dance at La Te Da, one of Key West's most dynamic venues. Renowned for dazzling drag shows featuring the charismatic…
Free
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
801 Karaoke – Hosted by Jeff
Join Jeff at 801 Bourbon Bar for an unforgettable karaoke experience in the heart of Old Town Key West. As an engaging and charismatic host,…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling World Famous 801 Girls at their 5pm show, where these talented drag queens bring glamour and energy to the stage. Held at…
QMitch Drag Queen Bingo at 22&Co
Join the vibrant atmosphere of 22&Co in Old Town Key West for QMitch Drag Queen Bingo. Hosted by the charismatic QMitch, this event promises an…
Free
Sunday Jazz at the Gardens
Enjoy a delightful evening at Sunday Jazz at the Gardens, featuring acclaimed jazz artists who bring soulful melodies to life in a serene tropical setting.…
Free
Sunset Celebration at Mallory Square
At Mallory Square's Sunset Celebration, experience Key West's lively atmosphere featuring a host of talented entertainers, including jugglers and the celebrated cat man. Against a…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the lively beats of Caribe of Key West at El Meson de Pepes on Mallory Square. This talented group energizes the atmosphere with their…
Oren Polak at Irish Kevin’s Bar
Oren Polak, a dynamic and versatile musician, captivates audiences at Irish Kevin’s Bar in Key West with his engaging performances and unique sound. Known for…
Free
80s & 90s Trivia Night
Join us for a memorable 80s & 90s Trivia Night at The Retro Room in Old Town Key West. Relive the good times with our…
Free
Karaoke at Bobby’s Monkey Bar
Experience lively karaoke nights at Bobby's Monkey Bar, set in the heart of Key West's Old Town. With an engaging entertainer leading the fun, guests…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain shines at Irish Kevin's Bar, captivating audiences with his vibrant performances and unique style. This Irish-born entertainer effortlessly blends traditional Irish music with…
Free