| Quin Lamar | 6-25-2025
Wednesday
8:00 PM | Key West Theater 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 |
| Jeff Dye | 6-29-2025
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Fighting For Laughs | 7-5-2025
Saturday
7:00 PM | Key West Theater in Key West, FL | View Tickets |
| Hilariously Inappropriate Drag Queen Bingo - A Comedy Show With Balls | 7-6-2025
Sunday
6:00 PM | Key West Theater 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 |
| Beehive | 7-29-2025
Tuesday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Beehive | 7-30-2025
Wednesday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Beehive | 7-31-2025
Thursday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Beehive | 8-1-2025
Friday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Beehive | 8-2-2025
Saturday
7:00 PM | Fringe Theater Key West in Key West, FL | View Tickets |
| Rum Fest: Cliff Cody & Sharese | 8-14-2025
Thursday
7:00 PM | Key West Theater in Key West, FL | View Tickets |
| Jesse Rice | 8-15-2025
Friday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| West Texas Symphony: Key Collaborations | 9-6-2025
Saturday
7:30 PM | Wagner Noel Performing Arts Center in Midland, TX | View Tickets |
| Key West | 9-26-2025
Friday
7:00 PM | Paramount Center For The Performing Arts in Bristol, TN | View Tickets |
| Puddles Pity Party | 9-28-2025
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Peter Antoniou | 10-11-2025
Saturday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Will Kimbrough | 10-31-2025
Friday
5:00 PM | Key West Theater in Key West, FL | View Tickets |
| Buffett Through The Years - Tribute to Jimmy Buffett | 10-31-2025
Friday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Dead-Zep | 11-1-2025
Saturday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Elton Dan and the Rocket Band | 11-12-2025
Wednesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Crystal Gayle | 11-22-2025
Saturday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Mac McAnally | 12-5-2025
Friday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| Mac McAnally | 12-6-2025
Saturday
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 |
| West Coast Hoops Showdown: Gonzaga Bulldogs Basketball vs. UCLA Bruins | 12-13-2025
Saturday
TBD | Climate Pledge Arena in Seattle, WA | View Tickets |
| Los Lobos | 1-13-2026
Tuesday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
| The Phil Collins Experience - Tribute | 1-26-2026
Monday
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 |
| Tommy Emmanuel | 3-22-2026
Sunday
8:00 PM | Key West Theater in Key West, FL | View Tickets |
