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,…
21 events found.
Events for May 18, 2026
Ongoing
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
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
Enjoy a serene yoga session at Fort Zachary Taylor State Park's stunning beach location. While an emphasis on the entertainer is absent, the park itself…
$20
Aqua Yoga at Southernmost Beach Resort
Join us at Southernmost Beach Resort for a unique Aqua Yoga experience. This tranquil oasis offers the perfect blend of modern luxury and tradition with…
$20
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck, a dynamic musician, takes the stage at Irish Kevin's Bar, infusing the lively venue with his captivating energy and musical talent. Located on…
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
Renowned for his vibrant performances, Jeff Harris graces Irish Kevin's Bar in Key West with his multifaceted talent. As a singer, songwriter, and comedian, his…
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
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
World Famous 801 Girls- 5pm Show
Experience the captivating performances of the World Famous 801 Girls during their 5pm matinee show at 801 Bourbon Bar in Key West. Known for their…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where the highlight is the captivating performances by street entertainers. With acts ranging from jugglers to the…
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 Pepes on Mallory Square. Caribe captivates audiences with lively performances that perfectly…
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin's Bar in Key West, Florida. Renowned for his captivating shows, he seamlessly blends music and entertainment…
Free
Martini Monday at Virgilios
Martini Monday at Virgilios in Old Town Key West offers an enchanting evening filled with live music that captivates the audience. As you savor premier…
Free
Charity Bingo at The Green Parrot
Join us for Charity Bingo at The Green Parrot in Key West, an iconic dive bar with a vibrant atmosphere. Discover captivating entertainment that elevates…
Free
Karaoke at Bobby’s Monkey Bar
Experience a vibrant night at Bobby's Monkey Bar in Key West's Old Town, featuring karaoke nightly in a lively island atmosphere. Though the entertainer details…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain brings a dynamic and unforgettable performance to Irish Kevin's Bar. An Irish-born musician, he captivates audiences with his unique blend of traditional Irish…
Free