| Nate Smith & Chase Matthew | 5-1-2025
Thursday
8:00 PM | Coffee Butler Amphitheater in Key West, FL | View Tickets |
| Dan Boulger | 5-1-2025
Thursday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Dan Boulger | 5-2-2025
Friday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Dan Boulger | 5-4-2025
Sunday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| The Comedy Music Jam | 5-5-2025
Monday
8:00 PM | Comedy Key West in Key West, FL | View Tickets |
| Andy Fiori | 5-7-2025
Wednesday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Andy Fiori | 5-8-2025
Thursday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Paula Poundstone | 5-9-2025
Friday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Ed Larson | 5-9-2025
Friday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| The Magic of Motown | 5-10-2025
Saturday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Ed Larson | 5-10-2025
Saturday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Ed Larson | 5-11-2025
Sunday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| The Lost Boy - A Reading | 5-13-2025
Tuesday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Duane Betts & Palmetto Motel | 5-15-2025
Thursday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Aaron Berg | 5-15-2025
Thursday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Aaron Berg | 5-16-2025
Friday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Aaron Berg | 5-17-2025
Saturday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Mini Kiss | 5-18-2025
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Journeyman - Tribute to Eric Clapton | 5-20-2025
Tuesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Jimmy Cash | 5-21-2025
Wednesday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Jimmy Cash | 5-22-2025
Thursday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Key West Coast - Tribute Jimmy Buffet | 5-23-2025
Friday
7:00 PM | Goldfield Trading Post in Roseville, CA | View Tickets |
| Stomp | 5-23-2025
Friday
8:00 PM | Tennessee Williams Theatre in Key West, FL | View Tickets |
| Jimmy Cash | 5-23-2025
Friday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Stomp | 5-24-2025
Saturday
8:00 PM | Tennessee Williams Theatre in Key West, FL | View Tickets |
| Jimmy Cash | 5-24-2025
Saturday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Chris Tabb | 5-28-2025
Wednesday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Chris Tabb | 5-29-2025
Thursday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Chris Tabb | 5-30-2025
Friday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Chris Tabb | 5-31-2025
Saturday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Adrienne Lapalucci | 6-11-2025
Wednesday
8:00 PM | Comedy Key West in Key West, FL | View Tickets |
| Adrienne Lapalucci | 6-12-2025
Thursday
8:00 PM | Comedy Key West in Key West, FL | View Tickets |
| Adrienne Lapalucci | 6-13-2025
Friday
8:00 PM | Comedy Key West in Key West, FL | View Tickets |
| Adrienne Lapalucci | 6-14-2025
Saturday
8:00 PM | Comedy Key West in Key West, FL | View Tickets |
| A Fabulous Evening With Lillian Baxter | 6-25-2025
Wednesday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Eddie Ifft | 6-25-2025
Wednesday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| A Fabulous Evening With Lillian Baxter | 6-26-2025
Thursday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Eddie Ifft | 6-26-2025
Thursday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| A Fabulous Evening With Lillian Baxter | 6-27-2025
Friday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Eddie Ifft | 6-27-2025
Friday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| A Fabulous Evening With Lillian Baxter | 6-28-2025
Saturday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Eddie Ifft | 6-28-2025
Saturday
8:30 PM | Comedy Key West in Key West, FL | View Tickets |
| Kristin Key | 7-18-2025
Friday
6:30 PM | Funny Bone Comedy Club - Liberty Township in West Chester, OH | View Tickets |
| Kristin Key | 7-18-2025
Friday
9:00 PM | Funny Bone Comedy Club - Liberty Township in West Chester, OH | View Tickets |
| Jesse Rice | 8-15-2025
Friday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Key West | 9-26-2025
Friday
7:00 PM | Paramount Center For The Performing Arts in Bristol, TN | View Tickets |
| Elton Dan and the Rocket Band | 11-12-2025
Wednesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Anthony Rodia | 12-11-2025
Thursday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| The Massacoustics | 2-4-2026
Wednesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| The Massacoustics | 2-5-2026
Thursday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Changes in Latitudes - Jimmy Buffet Tribute | 3-3-2026
Tuesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
