Karaoke at Bobby’s Monkey Bar
Experience a lively island atmosphere at Bobby's Monkey Bar in Key West's Old Town, where karaoke nights shine with vibrant entertainment. The charismatic performers create…
23 events found.
Events for May 11, 2026
Ongoing
Mylo O’Maolain at Irish Kevin’s Bar
At Irish Kevin's Bar, Mylo O'Maolain captivates audiences with his dynamic performances and charismatic presence. Known for his engaging style and vibrant energy, Mylo ensures…
Free
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
Join a rejuvenating session of Yoga on the Beach at Fort Zachary Taylor State Park in Key West. Emphasizing breathtaking sunset views, this experience offers…
$20
Aqua Yoga at Southernmost Beach Resort
Experience the tranquility of Aqua Yoga at Southernmost Beach Resort in Key West, a luxurious island escape offering lush gardens and ocean views. Immerse yourself…
$20
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings electrifying energy to Irish Kevin’s Bar, captivating the audience with his dynamic performances. Nestled in Old Town Key West, this lively venue…
Free
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
Jeff Harris at Irish Kevin’s Bar
Experience the captivating artistry of Jeff Harris at Irish Kevin's Bar. A multi-talented American entertainer, Jeff seamlessly blends music and comedy, enchanting audiences with his…
Free
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
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
World Famous 801 Girls- 5pm Show
Experience the unparalleled charisma of the World Famous 801 Girls at their 5pm show. These dynamic drag queens captivate audiences with their dazzling performances and…
Glow Hours on Hugh’s View
Experience an enchanting evening at Glow Hours on Hugh's View, where vibrant performances by world-class artists light up the night. Set atop The Studios of…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where entertainers steal the show. Marvel at captivating performances by jugglers and the renowned cat man, set…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant sounds of Caribe of Key West at El Meson de Pepes on Mallory Square. This talented entertainer infuses lively Cuban rhythms into…
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin's Bar in Key West, captivating audiences with his vibrant and entertaining shows. Known for seamlessly blending…
Free
Martini Monday at Virgilios
Experience Martini Monday at Virgilio’s in Old Town Key West, where you can savor exquisite martinis and enjoy live performances every evening. This stylish lounge…
Free
Charity Bingo at The Green Parrot
Join us at The Green Parrot in Key West for Charity Bingo, where vibrant entertainment takes center stage in this historic dive bar. Enjoy the…
Free
Sean Patton at Comedy Key West
Sean Patton is a dynamic comedian renowned for his engaging storytelling and sharp wit. Based in New York, with roots in New Orleans, he captivates…
$35
Karaoke at Bobby’s Monkey Bar
Join the charismatic and talented performer at Bobby's Monkey Bar for an unforgettable night of karaoke in Key West's Old Town. The lively island atmosphere…
Mylo O’Maolain at Irish Kevin’s Bar
Experience the charismatic Mylo O’Maolain at Irish Kevin's Bar, where his lively performances captivate audiences in the heart of Old Town Key West. Known for…
Free