Karaoke at Bobby’s Monkey Bar
Experience lively karaoke nights at Bobby's Monkey Bar, set in the heart of Key West's Old Town. With an engaging entertainer leading the fun, guests…
21 events found.
Events for May 25, 2026
Ongoing
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain shines at Irish Kevin's Bar, captivating audiences with his vibrant performances and unique style. This Irish-born entertainer effortlessly blends traditional Irish music with…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing excursion at A & B Marina in Key West's historic seaport. While the details of the entertainer…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Experience serenity at Yoga on the Beach at Ft Zachary Taylor State Park in Key West. Enjoy sessions led by a renowned local yogi against…
$20
Aqua Yoga at Southernmost Beach Resort
Experience the serene practice of Aqua Yoga at Southernmost Beach Resort in Key West. Set amidst lush gardens and ocean views, this unique session is…
$20
Bradd Shadduck at Irish Kevin’s Bar
At the heart of Old Town Key West, Irish Kevin's Bar hosts Bradd Shadduck, a dynamic musician known for energizing audiences with his captivating performances.…
Free
Distillery Tour – Key West Legal Rum Distillery
Explore the Key West First Legal Rum Distillery, nestled in the Historic Seaport. Delight in daily tours and rum samples while embracing vibrant nightlife vibes.…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West First Legal Rum Distillery, where a charismatic entertainer will guide you through a lively mojito-making experience. Delight in…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for an unforgettable journey beneath the sea. While soaking in vibrant marine life through crystal-clear waters,…
$69.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
The Glass Bottom Boat Cruise in Key West offers a unique marine adventure, enhanced by a captivating entertainer who brings the vibrant sea life into…
$69.95
Jeff Harris at Irish Kevin’s Bar
Experience the magnetic charm of Jeff Harris at Irish Kevin’s Bar, where his dynamic blend of music and comedy steals the spotlight. This multi-talented American…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience an unforgettable adventure with Sunset Watersports' Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise in Key West. Guided by knowledgeable and engaging staff,…
$79.95
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West for an unforgettable maritime adventure. While the vibrant marine life and crystal-clear waters captivate, it's…
$69.95
World Famous 801 Girls- 5pm Show
Experience the dazzling performances of the World Famous 801 Girls at their 5pm show in Key West's 801 Bourbon Bar. These talented drag queens captivate…
Sunset Celebration at Mallory Square
Experience the Sunset Celebration at Mallory Square, where the star attraction is the talented street performers. From the mesmerizing jugglers to the well-known cat man,…
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. This family-owned gem enchants guests with its lively…
NY Pauly at Irish Kevin’s Bar
NY Pauly, a legendary performer at Irish Kevin's Bar in Key West, captivates audiences with his dynamic blend of music and entertainment. Renowned for his…
Free
Martini Monday at Virgilios
Experience the captivating sounds of talented musicians at Martini Monday at Virgilio's in Old Town Key West. This stylish cocktail lounge offers an impressive martini…
Free
Charity Bingo at The Green Parrot
Join us for an unforgettable night at Charity Bingo at The Green Parrot in Key West. Experience the vibrant atmosphere of this historic dive bar,…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant atmosphere at Bobby's Monkey Bar for an unforgettable karaoke night. The entertainer takes center stage, captivating the crowd with charisma and energy,…
Mylo O’Maolain at Irish Kevin’s Bar
Experience the energetic performance of Mylo O'Maolain at Irish Kevin's Bar, where his captivating act lights up the stage. Known for engaging his audience with…
Free