Key West Comedy Events
Displaying 1 event

North America > United States > Florida > Key West > Events > Concerts & Shows > Comedy

Key West Comedy Events

Key West brings its island spirit to the stage with live music, open-air concerts, and laid-back performances happening daily. From local bands to touring acts, enjoy entertainment with a tropical twist. See what’s playing during your stay.

2/27/2026
Colin Quinn

Colin Quinn, the celebrated comedian known for his sharp wit and candid humor, is set to take the stage at the Key West Theater. With a career spanning decades, Quinn has become a staple in the comedy world, renowned for his insightful observations a... Read more

Wednesday, February 25, 2026 8:00 PM - Dave Matthews Tribute Band
Friday, February 27, 2026 8:00 PM - Colin Quinn
Tuesday, March 3, 2026 8:00 PM - Changes In Latitudes (21 & Over)
11/20/2026 - 11/21/2026
Dusty Slay

Dusty Slay, known for his distinctive laid-back storytelling and sharp wit, is set to perform at the Key West Theater. Slay has quickly become a favorite in the comedy circuit, captivating audiences with his unique perspective on everyday life. His S... Read more

Wednesday, February 25, 2026 8:00 PM - Dave Matthews Tribute Band
Friday, February 27, 2026 8:00 PM - Colin Quinn
Tuesday, March 3, 2026 8:00 PM - Changes In Latitudes (21 & Over)

All upcoming events are listed on this page. You can view all regular performing shows by visiting the Key West Shows page.