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…
25 events found.
Events for May 16, 2026
Ongoing
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
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 Yoga on the Beach at Fort Zachary Taylor State Park in Key West for an invigorating experience amidst breathtaking sunset views. Enhance your well-being…
$20
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for an invigorating Prime of Life Yoga session at the beautiful Key West Tropical Forest & Botanical Garden. Monica, a celebrated yoga…
$20
Jeff Harris at Irish Kevin’s Bar
Jeff Harris, a dynamic American artist, graces Irish Kevin's Bar with his captivating performances. As a singer, songwriter, comedian, and author, Jeff effortlessly fuses music…
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
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Experience a lively tribute to iconic musician Jimmy Buffett as acclaimed entertainer Caleb Hogan takes the stage at Comedy Key West. Hogan embodies Buffett through…
$28
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
NY Pauly at Irish Kevin’s Bar
NY Pauly is a legendary performer at Irish Kevin's Bar in Key West, Florida, captivating audiences with his vibrant and unforgettable shows. Seamlessly blending music…
Free
Fishmonster Max- Daily Party Boat Fishing
Join Fishmonster Max for daily party boat fishing at A & B Marina in Key West's historic seaport. Enjoy the beautiful waterfront and lively atmosphere,…
$85.00
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 dazzling energy of the World Famous 801 Girls at their exclusive 5pm show. These exceptional drag queens bring charisma, uniqueness, and flair to…
Sunset Celebration at Mallory Square
Experience the captivating Sunset Celebration at Mallory Square, where vibrant street performers steal the show. Marvel at the famous cat man and talented jugglers as…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the vibrant sounds of Caribe of Key West, performing live at El Meson de Pepe’s on Mallory Square. This family-owned establishment in Key West…
Damon Fowler at Green Parrot Bar
Experience the dynamic talents of Damon Fowler at the Green Parrot Bar. Known for his electrifying guitar skills and soulful vocals, Damon captivates audiences with…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a charismatic and fun-loving performer known for delighting audiences with his humor and charm at Irish Kevin's Bar in Key West. His…
Free
Karaoke at Two Friends Patio
Experience an unforgettable evening at Two Friends Patio with lively karaoke entertainment stealing the spotlight. Hosted by charismatic entertainers, karaoke nights promise joy and laughter…
Free
Damon Fowler at Green Parrot Bar
Experience the electrifying performance of Damon Fowler at the iconic Green Parrot Bar. Renowned for his masterful fusion of blues, soul, and rock, Fowler captivates…
Free
Karaoke at Bobby’s Monkey Bar
Experience a night of vibrant entertainment at Bobby's Monkey Bar in Key West's Old Town, where the star of the show is the charismatic karaoke…
Jack and Jim Show at Irish Kevin’s Bar
Experience the electrifying Jack and Jim Show at Irish Kevin’s Bar, where captivating performers create a night to remember. With their dynamic energy and engaging…
Free
Damon Fowler at Green Parrot Bar
Damon Fowler, a masterful blues guitarist and soulful singer, captivates audiences at the Green Parrot Bar in Key West. Known for his electrifying performances and…
Free