| Event | Venue | Date/Time | |
| Duane Betts & Palmetto Motel | Key West Theater
Key West, FL | Thursday
5/15/2025
8:00 PM |  |
| Aaron Berg | Comedy Key West
Key West, FL | Thursday
5/15/2025
8:30 PM | |
| Aaron Berg | Comedy Key West
Key West, FL | Friday
5/16/2025
8:30 PM | |
| Aaron Berg | Comedy Key West
Key West, FL | Saturday
5/17/2025
8:30 PM | |
| Mini Kiss | Key West Theater
Key West, FL | Sunday
5/18/2025
8:00 PM | |
| Journeyman - Tribute to Eric Clapton | Key West Theater
Key West, FL | Tuesday
5/20/2025
8:00 PM | |
| Jimmy Cash | Comedy Key West
Key West, FL | Wednesday
5/21/2025
8:30 PM | |
| Jimmy Cash | Comedy Key West
Key West, FL | Thursday
5/22/2025
8:30 PM | |
| Stomp | Tennessee Williams Theatre
Key West, FL | Friday
5/23/2025
8:00 PM | |
| Jimmy Cash | Comedy Key West
Key West, FL | Friday
5/23/2025
8:30 PM | |
| Stomp | Tennessee Williams Theatre
Key West, FL | Saturday
5/24/2025
8:00 PM | |
| Jimmy Cash | Comedy Key West
Key West, FL | Saturday
5/24/2025
8:30 PM | |
| Chris Tabb | Comedy Key West
Key West, FL | Wednesday
5/28/2025
8:30 PM | |
| Chris Tabb | Comedy Key West
Key West, FL | Thursday
5/29/2025
8:30 PM | |
| Chris Tabb | Comedy Key West
Key West, FL | Friday
5/30/2025
8:30 PM | |
| Chris Tabb | Comedy Key West
Key West, FL | Saturday
5/31/2025
8:30 PM | |
| Adrienne Lapalucci | Comedy Key West
Key West, FL | Wednesday
6/11/2025
8:00 PM | |
| Adrienne Lapalucci | Comedy Key West
Key West, FL | Thursday
6/12/2025
8:00 PM | |
| Adrienne Lapalucci | Comedy Key West
Key West, FL | Friday
6/13/2025
8:00 PM | |
| Adrienne Lapalucci | Comedy Key West
Key West, FL | Saturday
6/14/2025
8:00 PM | |
| A Fabulous Evening With Lillian Baxter | Fringe Theater Key West
Key West, FL | Wednesday
6/25/2025
7:00 PM | |
| Eddie Ifft | Comedy Key West
Key West, FL | Wednesday
6/25/2025
8:30 PM | |
| A Fabulous Evening With Lillian Baxter | Fringe Theater Key West
Key West, FL | Thursday
6/26/2025
7:00 PM | |
| Eddie Ifft | Comedy Key West
Key West, FL | Thursday
6/26/2025
8:30 PM | |
| A Fabulous Evening With Lillian Baxter | Fringe Theater Key West
Key West, FL | Friday
6/27/2025
7:00 PM | |
| Eddie Ifft | Comedy Key West
Key West, FL | Friday
6/27/2025
8:30 PM | |
| A Fabulous Evening With Lillian Baxter | Fringe Theater Key West
Key West, FL | Saturday
6/28/2025
7:00 PM | |
| Eddie Ifft | Comedy Key West
Key West, FL | Saturday
6/28/2025
8:30 PM | |
| Jesse Rice | Key West Theater
Key West, FL | Friday
8/15/2025
8:00 PM | |
| Dead-Zep | Key West Theater
Key West, FL | Saturday
11/1/2025
8:00 PM | |
| Elton Dan and the Rocket Band | Key West Theater
Key West, FL | Wednesday
11/12/2025
8:00 PM | |
| Anthony Rodia | Key West Theater
Key West, FL | Thursday
12/11/2025
8:00 PM | |
| The Phil Collins Experience - Tribute | Key West Theater
Key West, FL | Monday
1/26/2026
8:00 PM | |
| The Massacoustics | Key West Theater
Key West, FL | Wednesday
2/4/2026
8:00 PM | |
| The Massacoustics | Key West Theater
Key West, FL | Thursday
2/5/2026
8:00 PM | |
| Changes in Latitudes - Jimmy Buffet Tribute | Key West Theater
Key West, FL | Tuesday
3/3/2026
8:00 PM | |
