Karaoke at Bobby’s Monkey Bar
Experience a night of vibrant entertainment at Bobby's Monkey Bar in Key West's Old Town, where the star of the show is the charismatic karaoke…
24 events found.
Events for May 17, 2026
Ongoing
Jack and Jim Show at Irish Kevin’s Bar
Experience the electrifying Jack and Jim Show at Irish Kevin’s Bar, where captivating performers create a night to remember. With their dynamic energy and engaging…
Free
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
Yoga on the Beach at Fort Zachary Taylor in Key West provides a serene setting with historic charm and stunning ocean views. The real highlight…
$20
Bradd Shadduck at Irish Kevin’s Bar
At Irish Kevin's Bar, Bradd Shadduck captivates audiences with his dynamic musical performances. Known for lively sets that engage the crowd, he enhances the vibrant…
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
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
Jeff Harris at Irish Kevin’s Bar
Experience the dynamic performance of Jeff Harris at Irish Kevin's Bar, where his talents as a singer-songwriter and comedian come to life. Known for his…
Free
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
Tea Dance at La Te Da
Experience an unforgettable evening at the Tea Dance at La Te Da in Key West. Enjoy the captivating performances of talented drag queen Randy Roberts,…
Free
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
801 Karaoke – Hosted by Jeff
Join the lively atmosphere at 801 Bourbon Bar's Karaoke night hosted by the charismatic Jeff. Nestled in Old Town Key West, Jeff's dynamic energy makes…
Free
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls deliver an electrifying 5pm drag show at the iconic 801 Bourbon Bar in Key West. Known for their charismatic performances…
QMitch Drag Queen Bingo at 22&Co
Experience the vibrant world of QMitch Drag Queen Bingo at 22&Co in Old Town Key West. Known for unforgettable performances, QMitch dazzles with charisma and…
Free
Sunday Jazz at the Gardens
Experience the enchanting Sunday Jazz at the Gardens, where the spotlight shines on renowned jazz performers amidst the lush, tropical backdrop of The Gardens Hotel.…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West enchants audiences at El Meson de Pepe's on Mallory Square. Known for their captivating live performances, Caribe infuses the vibrant Cuban…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square in Key West, where the famous cat man and other street performers captivate audiences against a stunning…
Free
Damon Fowler Soundcheck Set at Green Parrot Bar
Renowned blues guitarist Damon Fowler brings his soulful sound to the iconic Green Parrot Bar, captivating audiences with his masterful guitar skills and heartfelt vocals.…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak electrifies Irish Kevin's Bar with his dynamic performances and charismatic presence. As a versatile musician and band leader, he captivates audiences with his…
Free
80s & 90s Trivia Night
Join us for an unforgettable 80s & 90s Trivia Night at The Retro Room, featuring an engaging entertainer who will take you on a nostalgic…
Free
Karaoke at Bobby’s Monkey Bar
Experience an unforgettable evening at Bobby's Monkey Bar with dynamic karaoke sessions led by an engaging and talented entertainer. Nestled in Key West's Old Town,…
Mylo O’Maolain at Irish Kevin’s Bar
Immerse yourself in the vibrant performances of Mylo O'Maolain at Irish Kevin's Bar in Key West. An Irish-born musician, Mylo captivates crowds with his soulful…
Free