December 2026 Key West Events & Festivals

Plan your Key West trip with this calendar of December 2026 events, festivals, concerts, and things to do.

• Sunset Celebration at Mallory Square — December 1, 2026 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, street performers, and beautiful sunset views over the Gulf of Mexico. (Browse group: Arts & Culture)
• Key West Art Walk — December 1, 2026 · 6:00pm - 9:00pm: An evening of art and culture as local galleries open their doors for an art walk showcasing local artists and their works. (Browse group: Arts & Culture)
• Monthly Ukulele Night — December 2, 2026 · 8:00 PM – 11:00 PM · Green Parrot Bar: The Green Parrot Ukulele Association will hold their monthly meeting with co-hosts Bobby Howard, Wavy Dave, and bassist Bubba Lownote. Following the same format as the previous well-attended, high-spirited shindigs, the meeting will begin with a workshop at 8 p.m. for those just starting out on theinstrument. Basic instruction and chord and song sheets will be provided. At 9 p.m., there will be featured performers, an open mic and a play-along, in no particular order. For those who missed last month’s’s meeting, it was outstanding, with an ever-growing congregation of uke-bearing aficionados in attendance, most of whom crowded the stage for a few nimble and professional sing-along covers of popular songs to wrap up an already lively night. “It is obvious from recent month’s turnouts that there is a serious Key West ukulele scene simmering just below the surface,” said John Vagnoni, Green Parrot manager. “We also see this as a unique way for Key Westers to meet people and make music at the same time.” Dig out that old ukulele from your attic or closet and strum your way into a four-string stupor at Green Parrot Ukulele night, Key West’s only ukulele-powered jam session. Come to just listen or join in. All levels are welcome and remember, spare ukes and instruction are available for those who want to try them out. (Browse group: Live Music)
• Happy Christmas Baby - Featuring the World’s Greatest Christmas Songs from ABBA to Bing Crosby (8PM) — December 2, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
• Happy Christmas Baby - Featuring the World’s Greatest Christmas Songs from ABBA to Bing Crosby (4PM) — December 2, 2026 · 4:00 PM (Doors 3:00 PM) · Key West Theater (Browse group: Arts & Culture)
• Sunset Celebration at Mallory Square — December 3, 2026 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, street performers, and beautiful sunset views over the Gulf of Mexico. (Browse group: Arts & Culture)
• Key West Farmers Market — December 3, 2026 · 1:00pm - 6:00pm · Truman Waterfront: A vibrant market featuring local produce, handmade goods, and unique crafts from local artisans. (Browse group: Food & Drink)
• Empire Strikes Brass at 5:30, 9:00 & 11:00 — December 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 Coming in from Asheville, NC band, Empire Strikes Brass, will take the stage for two performances. Their shows are high energy, reminiscent of old school funk, and rooted in the New Orleans brass band tradition of second-line parades and deep moving grooves. You won't want to miss this! (Browse group: Live Music)
• Empire Strikes Brass at 5:30, 9:00 & 11:00 — December 5, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 10:00-11:30, and 12:00-1:30 Coming in from Asheville, NC band, Empire Strikes Brass, will take the stage for two performances. Their shows are high energy, reminiscent of old school funk, and rooted in the New Orleans brass band tradition of second-line parades and deep moving grooves. You won't want to miss this! (Browse group: Live Music)
• Key West Artisan Market — December 5, 2026 · 10:00am - 2:00pm · Higgs Beach: A market featuring local artisans and their handmade goods, set in a beautiful beachside location. (Browse group: Food & Drink)
• Sunset Celebration at Mallory Square — December 5, 2026 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, street performers, and beautiful sunset views over the Gulf of Mexico. (Browse group: Arts & Culture)
• Empire Strikes Brass Soundcheck Set — December 6, 2026 · 5:30 PM – 7:00 PM · Green Parrot Bar: One 90-minute set: 5:30-7:00. Coming in from Asheville, NC band, Empire Strikes Brass, will take the stage for two performances. Their shows are high energy, reminiscent of old school funk, and rooted in the New Orleans brass band tradition of second-line parades and deep moving grooves. You won't want to miss this! (Browse group: Live Music)
• Bingo for Studios of Key West — December 7, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
• Banshee Tree at 5:30, 8:30 & 10:30 — December 8, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:30, and 11:00-12:30 Expanding the boundaries of rock, punk, swing, and Django-jazz, Banshee Tree hits the Parrot stage again for two nights. Fonted by guitarist and lead vocalist Thom LaFond and featuring drummer Michelle Pietrafitta, five-string violinist Nick Carter, bassist Jason Bertone, Banshee Tree is familiar to Parrot patrons from their past Coast is Clear Festival appearances. (Browse group: Festivals)
• Banshee Tree at 5:30, 8:30 & 10:30 — December 9, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00 and 10:30-12:00 Expanding the boundaries of rock, punk, swing, and Django-jazz, Banshee Tree hits the Parrot stage again for two nights. Fonted by guitarist and lead vocalist Thom LaFond and featuring drummer Michelle Pietrafitta, five-string violinist Nick Carter, bassist Jason Bertone, Banshee Tree is familiar to Parrot patrons from their past Coast is Clear Festival appearances. (Browse group: Festivals)
• Shaun Cassidy UNWRAPPED: Songs & Stories For The Holidays — December 10, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
• Sunset Celebration at Mallory Square — December 10, 2026 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, street performers, and beautiful sunset views over the Gulf of Mexico. (Browse group: Arts & Culture)
• Scott Kirby - 36 YEARS OF SONGS AND STORIES — December 10, 2026 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
• Holiday Parade — December 10, 2026 · 7:00pm · Duval Street: An annual holiday parade featuring festive floats, local marching bands, and a joyful atmosphere along Duval Street. (Browse group: Live Music)
• Sunset Celebration at Mallory Square — December 11, 2026 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, street performers, and beautiful sunset views over the Gulf of Mexico. (Browse group: Arts & Culture)
• Lighted Boat Parade — December 11, 2026 · 6:00pm · Key West Bight: A festive parade of brightly decorated boats sailing through the harbor, creating a magical holiday atmosphere. (Browse group: Community)
• Tim Palmieri & Friends at 5:30, 9:00 & 11:00 — December 11, 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 Tim Palimieri on Guitar/Vocals Rob Somerville on sax Beau Sasser on Bass/Keys Michelangelo Carruba on drums (Browse group: Nightlife)
• The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers — December 12, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
• Tim Palmieri & Friends at 5:30, 9:00 & 11:00 — December 12, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30Tim Palimieri on Guitar/Vocals Rob Somerville on sax Beau Sasser on Bass/Keys Michelangelo Carruba on drums (Browse group: Nightlife)
• Sunset Celebration at Mallory Square — December 12, 2026 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, street performers, and beautiful sunset views over the Gulf of Mexico. (Browse group: Arts & Culture)
• Tim Palmieri & Friends Soundcheck Set — December 13, 2026 · 5:30 PM – 7:00 PM · Green Parrot Bar: One 90-minute set: 5:30-7:00 Tim Palimieri on Guitar/Vocals Rob Somerville on sax Beau Sasser on Bass/Keys Michelangelo Carruba on drums (Browse group: Nightlife)
• Bingo for Sister Season Fund — December 14, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
• An Evening Aglow: A Candlelight Christmas with Marjory Lee — December 15, 2026 · 8:00 PM (Doors 6:30 PM) · Key West Theater (Browse group: Arts & Culture)
• Mac McAnally — December 18, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
• Dave Scher Band at 5:30, 9:00 & 11:00 — December 18, 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 Photo by Max Crace (Browse group: Live Music)
• Dave Scher Band at 5:30, 9:00 & 11:00 — December 19, 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 Photo by Max Crace (Browse group: Live Music)
• Mac McAnally — December 19, 2026 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
• Dave Scher Band Soundcheck Set — December 20, 2026 · 5:30 PM – 7:00 PM · Green Parrot Bar: One 90-minute set: 5:30-7:00. Photo by Max Crace (Browse group: Live Music)
• Bingo for Key West Art & Historical Society — December 21, 2026 · 7:00 PM – 9:00 PM · Green Parrot Bar: Join us every Monday night at 7:00 pm we bring the creative and artistic forces of our town together to create a great fundraising opportunity to benefit one of the many local non-profits of our little island. Prizes will be awarded after each round and cards are only $1.00 and 100% of money raised goes to the charity. (Browse group: Arts & Culture)
• Finley LaFond at 5:30, 8:30 & 10:30 — December 22, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00 & 10:30-12:00. Claire Finley and Thom LaFond ft. Neal Evans and Jesse Shantor (Browse group: Nightlife)
• Finley LaFond at 5:30, 8:30 & 10:30 — December 23, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00 & 10:30-12:00. Claire Finley and Thom LaFond ft. Neal Evans and Jesse Shantorc (Browse group: Nightlife)
• Gent Treadly at 5:30, 8:30 & 10:30 — December 24, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00, and 10:30-12:00 Led by Greg Koerner on bass, jam/rockers Gent Treadly bring their blend of world class improvisational roots/ rock, jam, and blues back to The Green Parrot. Gent Treadly featuring Greg Koerner on bass, trumpet icon Wild Willie Waldman (Snoop Dogg, Banyan, etc.), Doug South on guitar, and Ajay Sims behind the kit. Greg Koerner, a veteran of the Parrot stage, is pictured here both at last night’s show, and again, here in April 2006, backing Grateful Dead keyboardist Vince Welnick. (Browse group: Nightlife)
• Gent Treadly at 5:30, 9:00 & 11:00 — December 25, 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 Led by Greg Koerner on bass, jam/rockers Gent Treadly bring their blend of world class improvisational roots/ rock, jam, and blues back to The Green Parrot. Gent Treadly featuring Greg Koerner on bass, trumpet icon Wild Willie Waldman (Snoop Dogg, Banyan, etc.), Doug South on guitar, and Ajay Sims behind the kit. Greg Koerner, a veteran of the Parrot stage, is pictured here both at last night’s show, and again, here in April 2006, backing Grateful Dead keyboardist Vince Welnick. (Browse group: Nightlife)
• Scott Kirby - 36 YEARS OF SONGS AND STORIES with Gabriel Donohue — December 26, 2026 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
• Gent Treadly ft. Stanley Jordan at 5:30, 9:00 & 11:00 — December 26, 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 Led by Greg Koerner on bass, jam/rockers Gent Treadly bring their blend of world class improvisational roots/ rock, jam, and blues back to The Green Parrot. Gent Treadly featuring Greg Koerner on bass, trumpet icon Wild Willie Waldman (Snoop Dogg, Banyan, etc.), Doug South on guitar, and Ajay Sims behind the kit. Greg Koerner, a veteran of the Parrot stage, is pictured here both at last night’s show, and again, here in April 2006, backing Grateful Dead keyboardist Vince Welnick. (Browse group: Nightlife)