Key West Music Schedule
Live Music in Key West
Upcoming live shows by musicians and entertainers at bars around the island. Join the party! Come see a live performance! View Entertainment Schedule by Time
Boondocks Grille
Wednesday, Sep 16, 2026
- 6:00 PM - Jonathan Williams
- 6:00 PM - Jonathan Williams - Family Night
Hank's Hair of the Dog Saloon
Wednesday, Sep 16, 2026
- 4:00 PM - Shastina Chiles
- 8:00 PM - Rochi & Prince
Irish Kevin's
Wednesday, Sep 16, 2026
- 11:00 AM - Oren Polak
- 2:30 PM - Jon Hollywood
- 6:00 PM - Aaron Hudgins
- 10:00 PM - Tim Bradach
Rick's Bar Key West
Wednesday, Sep 16, 2026
- 3:00 PM - Harley Ray
- 7:00 PM - Andrew B.
- 7:00 PM - DJ Todd
- 8:00 PM - DJ Kori
- 11:00 PM - Karaoke w/ Davis
