Key West Events This Weekend

Find festivals, concerts, nightlife, and things to do in Key West this weekend.

Gulfstream Band — September 4, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
The Local Discounts — September 4, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Just a Few Friends Event feat. Gypsies in the Palace — September 4, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Steeln' Peaches at 5:30, 9:00 & 11:00 — September 4, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 Steeln' Peaches: an Allman Brothers Revue makes their much anticipated return to the Green Parrot stage. Paying tribute to the founding fathers of Southern rock and Spearheaded by Chuck Magid, whose incorporation of barn-burning lap-steel slide guitar gave the group inspiration for its name, “Steeln' Peaches-The Music of the All man Brothers Band" features some of Florida’s most exciting young musicians with Daniel Heitz, guitar, vocals; Aaron “Bucky” Buckingham, drums, vocals; Glenn Kastrinos, bass, vocals; Colin Fei, keyboards, vocals; and David Vanegas, percussion, vocals. (Browse group: Live Music)
Sunset Celebration — September 4, 2026 · 6:27pm · Mallory Square: Join the crowd at Mallory Square for the Sunset Celebration, a beloved Key West tradition with entertainment and local crafts. (Browse group: Community)
Cliff Cody — September 5, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Occupational Hazard, The First Coral Reefers - SOLD OUT — September 5, 2026 · 2:00 PM (Doors 1:00 PM) · Key West Theater (Browse group: Arts & Culture)
Just a Few Friends Event feat. Gypsies in the Palace — September 5, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Steeln' Peaches at 5:30, 9:00 & 11:00 — September 5, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 Steeln' Peaches: an Allman Brothers Revue makes their much anticipated return to the Green Parrot stage. Paying tribute to the founding fathers of Southern rock and Spearheaded by Chuck Magid, whose incorporation of barn-burning lap-steel slide guitar gave the group inspiration for its name, “Steeln' Peaches-The Music of the All man Brothers Band" features some of Florida’s most exciting young musicians with Daniel Heitz, guitar, vocals; Aaron “Bucky” Buckingham, drums, vocals; Glenn Kastrinos, bass, vocals; Colin Fei, keyboards, vocals; and David Vanegas, percussion, vocals. (Browse group: Live Music)
Sunset Celebration — September 5, 2026 · 6:26pm · Mallory Square: Don't miss the Sunset Celebration at Mallory Square, where you can enjoy live music, food vendors, and the breathtaking sunset. (Browse group: Live Music)
Gulfstream Band — September 5, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Cayman And The Mango Men: A Buffett Tribute Soundcheck Set — September 6, 2026 · 5:30 PM – 7:00 PM · Green Parrot Bar: One 90-minute set: 5:30-7:00 Join us for a special Soundcheck set to celebrate Jimmy Buffet lead by our friend (and Jimmy's) Cayman Smith-Martin. When life gives you limes, make margaritas. (Browse group: Arts & Culture)
Gulfstream Band — September 6, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
The Local Discounts — September 6, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
McKenna Carlson — September 6, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Womenfest — September 6, 2026: Womenfest is a celebration of women, featuring a variety of events including parties, workshops, and entertainment throughout Key West. (Browse group: Arts & Culture)
Jess and Jill at 12:00 & 2:00 — September 6, 2026 · 12:00 PM – 4:30 PM · Green Parrot Bar: Two 90-minute sets: 12:00-1:30 and 2:30-4:00 (ish) Jesse Wagner and Jillian Todd bring us sweet originals and harmonic covers. They won Duo Of The Year at the 2024 Iggies, Key West Music Awards. (Browse group: Live Music)