Karaoke at Bobby’s Monkey Bar
Join the vibrant nightlife at Bobby's Monkey Bar for unforgettable karaoke sessions hosted by dynamic entertainers who know how to engage the crowd. Set in…
20 events found.
Events for May 31, 2026
Ongoing
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
Experience tranquility with Yoga on the Beach at Fort Zachary Taylor in Key West. Despite the lack of a specific entertainer, this serene outdoor session…
$20
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
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
Trae Pierce & The T-Stones Soundcheck Set at Green Parrot Bar
Experience the electrifying performance of Trae Pierce & The T-Stones at the renowned Green Parrot Bar in Key West. Known for his dynamic stage presence…
Free
Tea Dance at La Te Da
Experience the vibrant Tea Dance at La Te Da in Key West, where the spotlight is on the extraordinary performances by drag star Randy Roberts.…
Free
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
801 Karaoke – Hosted by Jeff
Join the vibrant atmosphere of 801 Bourbon Bar in Old Town Key West for an unforgettable karaoke night hosted by the charismatic Jeff. Known for…
Free
World Famous 801 Girls- 5pm Show
Experience the charismatic performances of the World Famous 801 Girls during the 5pm show at 801 Bourbon Bar, nestled in Old Town Key West. These…
QMitch Drag Queen Bingo at 22&Co
QMitch captivates audiences at 22&Co in Key West with her vibrant drag queen bingo performances. Known for her dynamic presence and charismatic flair, QMitch transforms…
Free
Sunday Jazz at the Gardens
Sunday Jazz at the Gardens features captivating performances by talented jazz musicians in a lush, tropical setting at The Gardens Hotel in Key West. Enjoy…
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 Pepe's on Mallory Square. This talented band captivates audiences with their energetic…
Sunset Celebration at Mallory Square
Experience the lively Sunset Celebration at Mallory Square, where street performers and entertainers take center stage. Marvel at the famous cat man's astonishing feline tricks…
Free
Full Moon Lighted Bike Ride
Experience the enchanting Full Moon Lighted Bike Ride at White Street Pier in Key West. While the location offers stunning oceanfront views and a peaceful…
80s & 90s Trivia Night
Join us for an unforgettable 80s & 90s Trivia Night at The Retro Room in Old Town Key West. Our charismatic entertainer will guide you…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant island atmosphere at Bobby's Monkey Bar for a night of karaoke fun. With talented local performers leading the charge, the lively ambiance…