| Event | Venue | Date/Time | |
| Keys Choral Arts: Holiday Concert | Tennessee Williams Theatre
Key West, FL | Sunday
12/14/2025
4:00 PM |  |
| Mike Vecchione | Comedy Key West
Key West, FL | Tuesday
12/16/2025
8:30 PM | |
| Schmaltz and Pepper | Tennessee Williams Theatre
Key West, FL | Tuesday
1/6/2026
7:30 PM | |
| David Nihill | Key West Theater
Key West, FL | Sunday
1/11/2026
6:00 PM | |
| Los Lobos | Key West Theater
Key West, FL | Tuesday
1/13/2026
8:00 PM | |
| The Expanding Man - Tribute To Steely Dan | Key West Theater
Key West, FL | Wednesday
1/14/2026
8:00 PM | |
| Asleep At The Wheel | Key West Theater
Key West, FL | Thursday
1/15/2026
8:00 PM | |
| Martina Bevis | Tennessee Williams Theatre
Key West, FL | Friday
1/16/2026
7:30 PM | |
| Kash'd Out | Key West Theater
Key West, FL | Friday
1/16/2026
8:00 PM | |
| The Coral Reefer Band | Coffee Butler Amphitheater
Key West, FL | Friday
1/16/2026
8:00 PM | |
| Direct From Sweden - The Music of ABBA | Tennessee Williams Theatre
Key West, FL | Wednesday
1/21/2026
7:30 PM | |
| Rumours ATL - A Fleetwood Mac Tribute | Key West Theater
Key West, FL | Wednesday
1/21/2026
8:00 PM | |
| Young Dubliners | Key West Theater
Key West, FL | Friday
1/23/2026
8:00 PM | |
| South Florida Symphony Orchestra: Vaughan Williams - Sibelius' Symphony No. 2 & Ravel's Piano Concerto | Tennessee Williams Theatre
Key West, FL | Saturday
1/24/2026
7:30 PM | |
| Paradise Big Band | Tennessee Williams Theatre
Key West, FL | Sunday
1/25/2026
7:30 PM | |
| The Phil Collins Experience - Tribute | Key West Theater
Key West, FL | Monday
1/26/2026
8:00 PM | |
| Mile 0 Fest Key West - Tuesday | Truman Waterfront Amphitheater
Key West, FL | Tuesday
1/27/2026
5:00 PM | |
| Mile 0 Fest Key West: Stephen Wilson Jr., American Aquarium & Taylor Hunnicut - Wednesday | Truman Waterfront Amphitheater
Key West, FL | Wednesday
1/28/2026
4:00 PM | |
| Mile 0 Fest Key West: Randy Rogers Band, Kaitlin Butts & Tanner Usrey - Thursday | Truman Waterfront Amphitheater
Key West, FL | Thursday
1/29/2026
4:00 PM | |
| Mile 0 Fest Key West: Paul Cauthen, Cody Canada and The Departed & Them Dirty Roses - Friday | Truman Waterfront Amphitheater
Key West, FL | Friday
1/30/2026
4:00 PM | |
| Mile 0 Fest Key West: Shane Smith and The Saints, Casey Donahew & The Band of Heathens - Saturday | Truman Waterfront Amphitheater
Key West, FL | Saturday
1/31/2026
4:00 PM | |
| The Massacoustics | Key West Theater
Key West, FL | Wednesday
2/4/2026
8:00 PM | |
| Vienna Boys Choir | Tennessee Williams Theatre
Key West, FL | Thursday
2/5/2026
7:30 PM | |
| The Massacoustics | Key West Theater
Key West, FL | Thursday
2/5/2026
8:00 PM | |
| New York Philharmonic String Quartet | Tennessee Williams Theatre
Key West, FL | Tuesday
2/10/2026
7:30 PM | |
| Pilobolus | Tennessee Williams Theatre
Key West, FL | Friday
2/13/2026
7:30 PM | |
| Benmont Tench | Key West Theater
Key West, FL | Friday
2/13/2026
8:00 PM | |
| A Tribute to the Songs of Pat Dailey | Key West Theater
Key West, FL | Saturday
2/14/2026
8:00 PM | |
| Gabriel Rutledge | Key West Theater
Key West, FL | Sunday
2/15/2026
8:00 PM | |
| Yachtley Crew | Key West Theater
Key West, FL | Wednesday
2/18/2026
8:00 PM | |
| Marty Stuart and His Fabulous Superlatives | Key West Theater
Key West, FL | Thursday
2/19/2026
8:00 PM | |
| South Florida Symphony Orhcestra: Rimsky-Korsakov’s Capriccio, Mozart, & Simon and Joachim | Tennessee Williams Theatre
Key West, FL | Saturday
2/21/2026
7:30 PM | |
| The Linda Ronstadt Experience | Key West Theater
Key West, FL | Saturday
2/21/2026
8:00 PM | |
| Dave Matthews Tribute Band | Key West Theater
Key West, FL | Wednesday
2/25/2026
8:00 PM | |
| Neil Berg's 50 Years of Rock & Roll | Tennessee Williams Theatre
Key West, FL | Friday
2/27/2026
7:30 PM | |
| Rick Thomas | Tennessee Williams Theatre
Key West, FL | Tuesday
3/3/2026
7:30 PM | |
| Changes in Latitudes - Jimmy Buffet Tribute | Key West Theater
Key West, FL | Tuesday
3/3/2026
8:00 PM | |
| The Man In Black: Tribute To Johnny Cash | Key West Theater
Key West, FL | Thursday
3/5/2026
8:00 PM | |
| Bobby in the Lobby | Tennessee Williams Theatre
Key West, FL | Sunday
3/8/2026
7:30 PM | |
| Bobby in the Lobby | Tennessee Williams Theatre
Key West, FL | Monday
3/9/2026
7:30 PM | |
| The Doo Wop Project | Tennessee Williams Theatre
Key West, FL | Wednesday
3/11/2026
7:30 PM | |
| Martin Sexton | Key West Theater
Key West, FL | Friday
3/13/2026
8:00 PM | |
| South Florida Symphony Orhcestra: Dvorak & Sibelius | Tennessee Williams Theatre
Key West, FL | Saturday
3/14/2026
7:30 PM | |
| The Reverend Peyton's Big Damn Band | Key West Theater
Key West, FL | Saturday
3/21/2026
8:00 PM | |
| Paradise Big Band | Tennessee Williams Theatre
Key West, FL | Sunday
3/22/2026
7:30 PM | |
| Tommy Emmanuel | Key West Theater
Key West, FL | Sunday
3/22/2026
8:00 PM | |
| Jazz At Lincoln Center: Great American Crooners | Tennessee Williams Theatre
Key West, FL | Tuesday
3/24/2026
7:30 PM | |
| 7 Bridges - Eagles Tribute Band | Key West Theater
Key West, FL | Friday
3/27/2026
8:00 PM | |
| BoDeans | Key West Theater
Key West, FL | Sunday
3/29/2026
8:00 PM | |
| Houston Ballet II | Tennessee Williams Theatre
Key West, FL | Monday
3/30/2026
7:30 PM | |
| Squirrel Nut Zippers | Key West Theater
Key West, FL | Thursday
4/2/2026
8:00 PM | |
| Belle Jampol | Tennessee Williams Theatre
Key West, FL | Saturday
4/4/2026
7:30 PM | |
| Puppy Pals | Tennessee Williams Theatre
Key West, FL | Monday
4/6/2026
6:30 PM | |
| Crystal Gayle | Key West Theater
Key West, FL | Tuesday
4/7/2026
8:00 PM | |
| Jillian Todd | Tennessee Williams Theatre
Key West, FL | Wednesday
4/15/2026
7:30 PM | |
| Dusty Slay | Key West Theater
Key West, FL | Saturday
4/18/2026
8:00 PM | |
| Foreigner & Lou Gramm | Coffee Butler Amphitheater
Key West, FL | Thursday
4/23/2026
8:00 PM | |
| Graham Nash | Key West Theater
Key West, FL | Saturday
4/25/2026
8:00 PM | |
| Graham Nash | Key West Theater
Key West, FL | Sunday
4/26/2026
8:00 PM | |
| One Night of Queen | Tennessee Williams Theatre
Key West, FL | Sunday
5/3/2026
7:30 PM | |
