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…
24 events found.
Events for May 3, 2026
Ongoing
Jack and Jim Show at Irish Kevin’s Bar
Experience the infectious energy of the Jack and Jim Show at Irish Kevin’s Bar, where talented entertainers captivate audiences with their lively performances. Set in…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing adventure at A & B Marina in Key West's historic seaport. Enjoy a vibrant atmosphere with live…
$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
Local’s Day at The Key West Tropical Forest & Botanical Garden
Local's Day at The Key West Tropical Forest & Botanical Garden invites visitors to immerse themselves in a vibrant showcase of local flora and fauna.…
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck electrifies the stage at Irish Kevin's Bar in Key West with his dynamic performances. Known for his engaging style, Bradd captivates audiences with…
Free
Distillery Tour – Key West Legal Rum Distillery
Experience the vibrant nightlife atmosphere at Key West First Legal Rum Distillery. Enjoy free daily tours and tastings in this historic seaport location, once a…
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 of four people for an unforgettable experience. Enjoy lively entertainment as expert…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Experience the Glass Bottom Boat Cruise in Key West, where a charming entertainer guides you through the vibrant marine life visible beneath your feet. With…
$69.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West where the stars of the show are the vibrant marine life visible through the crystal-clear…
$69.95
Jeff Harris at Irish Kevin’s Bar
Experience the captivating talent of Jeff Harris at Irish Kevin's Bar in Key West. A multi-talented American artist, Jeff effortlessly blends music and comedy, delivering…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Join Sunset Watersports in Key West's Historic Seaport for an unforgettable adventure. Although details about the entertainer are sparse, the experienced staff ensures a thrilling…
$79.95
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
Join us for the Glass Bottom Boat Cruise in Key West, a unique journey showcasing the magical underwater world. Delight in live entertainment that enhances…
$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
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
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…
Oren Polak at Irish Kevin’s Bar
Oren Polak is a dynamic musician and band leader performing at Irish Kevin's Bar in Key West. Renowned for his versatile talent and engaging charisma,…
Free
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…
Mylo O’Maolain at Irish Kevin’s Bar
Experience the vibrant energy of Mylo O'Maolain at Irish Kevin's Bar. Renowned for his engaging performances, Mylo captivates audiences with his dynamic blend of music…
Free