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…
22 events found.
Events for May 4, 2026
Ongoing
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
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 renowned yoga instructor for a rejuvenating session at Fort Zachary Taylor State Park in Key West. Experience the perfect blend of relaxation and history,…
$20
Aqua Yoga at Southernmost Beach Resort
Experience Aqua Yoga at Southernmost Beach Resort, a luxurious island escape. Although specific entertainer details are sparse, join this serene session in a setting of…
$20
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck energizes Irish Kevin’s Bar with his captivating musical performances. As a talented musician, he brings an infectious energy that keeps the crowd engaged…
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
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 dynamic energy of Jeff Harris at Irish Kevin's Bar in Old Town Key West. This multi-talented entertainer blends music and comedy, captivating audiences…
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
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
World Famous 801 Girls- 5pm Show
Experience the dazzling talent of the World Famous 801 Girls during their 5pm show at 801 Bourbon Bar in Key West's Old Town. This vibrant…
Glow Hours on Hugh’s View
Experience a magical evening at Glow Hours on Hugh's View at The Studios of Key West, featuring captivating performances by world-class artists. Enjoy live music…
Sunset Celebration at Mallory Square
Experience the lively atmosphere at Mallory Square's Sunset Celebration, a must-visit Key West attraction. Be captivated by talented street performers, including the renowned cat man,…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant energy of Caribe of Key West at El Meson de Pepe's on Mallory Square. Renowned for delivering exhilarating live performances, Caribe brings…
NY Pauly at Irish Kevin’s Bar
NY Pauly, a legendary performer at Irish Kevin's Bar in Key West, captivates audiences with his vibrant shows. Blending music and entertainment seamlessly, he creates…
Free
Martini Monday at Virgilios
Join us at Martini Monday at Virgilios in Old Town Key West for an unforgettable evening. As you savor exquisite martinis and Italian cuisine, enjoy…
Free
Charity Bingo at The Green Parrot
Join Charity Bingo at The Green Parrot in Key West, where an incredible entertainer awaits to elevate your evening. Experience the magic of this iconic…
Free
Karaoke at Bobby’s Monkey Bar
Karaoke at Bobby's Monkey Bar features an energetic and charismatic host who brings the crowd to life every night. Nestled in Key West's Old Town,…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O’Maolain captivates audiences at Irish Kevin’s Bar with his dynamic performances and engaging stage presence. Known for his energetic and interactive shows, Mylo keeps…
Free