December 2026 Key West Events & Festivals

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

• Key West Art Walk — December 1, 2026 · 6:00pm - 9:00pm: A monthly event where local galleries open their doors for an evening of art, music, and community. (Browse group: Live Music)
• 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)
• 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)
• Key West Farmers Market — December 3, 2026 · 1:00pm - 6:00pm · Truman Waterfront: A vibrant market featuring local produce, crafts, and food vendors every Thursday. (Browse group: Food & Drink)
• Sunset Celebration — December 3, 2026 · 5:30pm · Mallory Square: Join locals and visitors alike for a nightly celebration of the sunset with street performers and local artisans. (Browse group: Arts & Culture)
• 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)
• 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)
• Sunset Celebration — December 10, 2026 · 5:30pm · Mallory Square: Join locals and visitors alike for a nightly celebration of the sunset with street performers and local artisans. (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)
• 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)
• Key West Farmers Market — December 10, 2026 · 1:00pm - 6:00pm · Truman Waterfront: A vibrant market featuring local produce, crafts, and food vendors every Thursday. (Browse group: Food & Drink)
• Lighted Boat Parade — December 10, 2026 · 6:00pm · Key West Bight: A festive parade of beautifully decorated boats sailing through the harbor, celebrating the holiday season. (Browse group: Community)
• 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)
• 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)
• Sunset Celebration — December 17, 2026 · 5:30pm · Mallory Square: Join locals and visitors alike for a nightly celebration of the sunset with street performers and local artisans. (Browse group: Arts & Culture)
• Key West Farmers Market — December 17, 2026 · 1:00pm - 6:00pm · Truman Waterfront: A vibrant market featuring local produce, crafts, and food vendors every Thursday. (Browse group: Food & Drink)
• Holiday Parade — December 17, 2026 · 7:00pm · Duval Street: A festive parade featuring floats, music, and holiday cheer as it travels down Duval Street. (Browse group: Live Music)
• Key West Artisan Market — December 18, 2026 · 10:00am - 2:00pm · Higgs Beach: A market featuring local artisans and their crafts, perfect for holiday shopping. (Browse group: Food & Drink)
• Sunset Celebration — December 24, 2026 · 5:30pm · Mallory Square: Join locals and visitors alike for a nightly celebration of the sunset with street performers and local artisans. (Browse group: Arts & Culture)
• 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)
• New Year's Eve Celebration — December 31, 2026 · 8:00pm · Sloppy Joe's Bar: Ring in the New Year at Sloppy Joe's with live music, festivities, and a countdown to midnight. (Browse group: Live Music)