Wednesday Filet Day at Mary Ellen’s
Join the lively atmosphere at Mary Ellen's in Old Town Key West for Wednesday Filet Day. Enjoy classic American comfort food, including mouthwatering gourmet grilled…
Free
24 events found.
Events for May 14, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Enjoy an unforgettable evening at Bobby's Monkey Bar, where the charismatic karaoke host steals the show. With their energetic presence, they turn every night into…
Kari Wolf at Irish Kevin’s Bar
Kari Wolf brings her dynamic presence to Irish Kevin’s Bar, captivating audiences with soulful melodies and a unique style. As a celebrated musician from Key…
Free
Ambitious Morning Runners
The Ambitious Morning Runners event at White Street Pier in Key West features live entertainment against a stunning oceanfront backdrop. As runners gather to experience…
Free
Yoga on the Beach – Ft Zachary Taylor
Experience tranquility at Yoga on the Beach with renowned instructor in the serene setting of Fort Zachary Taylor State Park, Key West. Enjoy a unique…
$20
Prime of Life Yoga with Monica Haskell
Join Monica Haskell for Prime of Life Yoga at the Key West Tropical Forest & Botanical Garden. Monica brings her expertise to this serene setting,…
$20
Mylo O’Maolain at Irish Kevin’s Bar
Experience the vibrant energy of Mylo O'Maolain at Irish Kevin's Bar in Key West. Known for his captivating performances, Mylo engages the crowd with his…
Free
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Experience Caleb Hogan as a captivating tribute to Jimmy Buffett in A Pirate Looks Back at Comedy Key West. Dive into an immersive musical journey…
$28
Truman Waterfront Farmers Market
At Truman Waterfront Farmers Market in Key West, enjoy lively performances at the amphitheater amidst a vibrant community setting. While vibrant stalls offer local produce…
Free
Irish Kevin at Irish Kevin’s Bar
Irish Kevin is a charismatic entertainer known for his humor and infectious energy at Irish Kevin's Bar in Key West. With a genuine spirit and…
Free
World Famous 801 Girls- 5pm Show
Experience the captivating World Famous 801 Girls at their 5pm show, where talented drag queens dazzle the stage with charisma and flair. Held at 801…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square in Key West where talented street performers take center stage. Revel in the artistry of jugglers and…
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 Pepes on Mallory Square. This captivating entertainer brings the spirit of Cuban…
Have Gun Will Travel at Green Parrot Bar
Have Gun Will Travel brings their captivating live performance to the iconic Green Parrot Bar in Key West. The band's dynamic sound and engaging stage…
Free
Bria Ansara at Berlin’s Cocktail Bar
Bria Ansara enchants patrons at Berlin's Cocktail Bar with her captivating performance. Her jazz-infused vocals and magnetic stage presence create an unforgettable experience. As guests…
Free
Filming Sit with Kit Podcast Episodes
Join the captivating entertainer Mr. Kit Carson at Angelina's Pizzeria in Key West for the Filming Sit with Kit podcast episodes. Engage in vibrant discussions…
Free
Oren Polak at Irish Kevin’s Bar
Oren Polak brings his captivating performances and unique sound to Irish Kevin's Bar in Key West. A versatile musician and band leader, Oren engages the…
Free
Catch The Mania Trivia at Brady’s Pub
Join the excitement at Brady's Pub for Catch The Mania Trivia, hosted by a dynamic entertainer who brings energy and fun to every question. Enjoy…
Free
Andy’s Cabana Open Mic No Mic Night
Andy's Cabana showcases a unique night where talented performers captivate audiences in an intimate environment, relying solely on their pure acoustic sounds. Nestled in Key…
Free
Have Gun Will Travel at Green Parrot Bar
Experience the dynamic sounds of Have Gun Will Travel at the iconic Green Parrot Bar in Key West. Known for their compelling blend of Americana…
Free
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
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
Have Gun Will Travel at Green Parrot Bar
Experience the captivating sounds of Have Gun Will Travel at Green Parrot Bar in Key West. This renowned ensemble promises a night of dynamic live…
Free