Karaoke with Foss at RockHouse Live
Join Foss for an electrifying night of karaoke at RockHouse Live in Key West. Known for his dynamic stage presence, Foss elevates the karaoke experience,…
Free
27 events found.
Events for May 15, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Enjoy electrifying evenings with top-notch entertainers at Bobby's Monkey Bar's karaoke nights. Nestled in Key West's Old Town, the bar boasts a lively island atmosphere…
Riptide Riot at Irish Kevin’s Bar
Riptide Riot is a dynamic power duo captivating audiences at Irish Kevin's Bar in Key West. Consisting of Jim Simonian on drums and Tim Bradach…
Free
Yoga on the Beach – Smather’s Beach
Join an invigorating Yoga on the Beach session at Smathers Beach in Key West. Led by an experienced instructor, you'll find peace and tranquility amidst…
$20
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
Join us for a serene yoga session guided by an inspiring instructor at the picturesque Fort Zachary Taylor State Park in Key West. Amidst historic…
$20
Story Time at the Key West Library
Experience a captivating Story Time at the Key West Library, led by a talented and engaging entertainer who brings tales to life with dynamic storytelling…
Free
Jeff Harris at Irish Kevin’s Bar
Jeff Harris, a dynamic American artist, will captivate audiences at Irish Kevin's Bar with his unique blend of music and comedy. Known for his heartfelt…
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
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
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
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Experience the charismatic Caleb Hogan as he transforms into Jimmy Buffett in A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West. This…
$28
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
Mylo O’Maolain at Irish Kevin’s Bar
Experience the vibrant energy of Mylo O'Maolain at Irish Kevin’s Bar in Key West. This Irish-born entertainer captivates audiences with his unique blend of traditional…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for a thrilling daily party boat fishing adventure at A & B Marina in Key West's historic seaport. While enjoying the vibrant…
$85.00
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. These talented drag queens captivate audiences at the vibrant 801 Bourbon…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square, where entertainers captivate audiences with their unique artistry. Watch the famous cat man and jugglers perform amidst…
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. This talented entertainer brings the authentic sounds of…
Damon Fowler at Green Parrot Bar
Experience the electrifying performance of Damon Fowler at Green Parrot Bar, Key West's iconic dive bar. Known for his soulful voice and masterful guitar skills,…
Free
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary entertainer at Irish Kevin's Bar in Key West, Florida. Renowned for his captivating performances, he effortlessly blends music and entertainment,…
Free
Karaoke at Two Friends Patio
Join the lively Karaoke at Two Friends Patio, where talented entertainers light up the open-air venue with energetic performances. Located near Mallory Square, this Key…
Free
Damon Fowler at Green Parrot Bar
Damon Fowler takes the stage at the iconic Green Parrot Bar, captivating audiences with his soulful blend of blues, roots, and rock music. Known for…
Free
Karaoke at Bobby’s Monkey Bar
Experience unforgettable evenings at Bobby's Monkey Bar in Key West, where a dynamic entertainer leads karaoke nights, transforming the lively island atmosphere into a vibrant…
Riptide Riot at Irish Kevin’s Bar
Riptide Riot, a dynamic power duo from Key West, electrifies audiences at Irish Kevin's Bar. Featuring Jim Simonian on drums and Tim Bradach on guitar,…
Free
Damon Fowler at Green Parrot Bar
Damon Fowler, a masterful blues guitarist and soulful singer, will electrify the Green Parrot Bar's stage in Key West. Known for his slide guitar prowess…
Free