Key West Comedy Events

Bubba Look Alike Contest

200 Duval St, Key West, FL 33040, United States 4 Sep 2026

A Pirate Looks Back - Jimmy Buffett Tribute

Comedy Key West 5 Sep 2026

Illusions The Drag Queen Show Key West - Drag Queen Show - Key West, FL

Illusions the Drag Queen Show Key West 21 Aug 2026

A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show

218 Whitehead St, Key West, FL 33040-6595, United States 2 Sep 2026

John Frinzi & Aaron Scherz

Key West Theater 2 Sep 2026

John Frinzi & Aaron Scherz

Key West Theater 3 Sep 2026

Drag Brunch

291 Front St suite 207, Key West, FL, United States, Florida 33040 6 Sep 2026

Pencil Thin Mustache Contest

Pier House Resort & Spa 7 Sep 2026

Pirate Looks Back Tribute Show: Ultimate Friends Edition

218 Whitehead St, Key West, FL 33040-6595, United States 4 Sep 2026

Key of Bones: Curse of the Ghost Pirate – Key West Red Carpet Premiere

Tennessee Williams Theatre 2 Oct 2026

A Tribute to the Songs of Pete & Wayne with Pete Jarvis, Larry Strickland, Ray Fogg & Special Guests

Key West Theatre 14 Nov 2026

Dusty Slay

Key West Theater 20 Nov 2026

Dusty Slay

Key West Theater 21 Nov 2026

Dusty Slay

Key West, Florida 20 Nov 2026

Brian Patafie

Key West Theater 7 Jan 2027

In Cahoots

Key West Theater 11 Feb 2027

Illusions The Drag Brunch Key West-Drag Queen Brunch-Key West, FL

Illusions the Drag Queen Brunch Key West 22 Aug 2026

Paul Mecurio - Permission to Speak at Key West Theater

Key West Theater 27 Feb 2027

Brian Patafie (9:00PM)

Key West Theater 6 Jan 2027

Dusty Slay at Key West Theater

Key West Theater 21 Nov 2026