January 2027 Key West Events & Festivals

Plan your Key West trip with this calendar of January 2027 events, festivals, concerts, and things to do.

The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band — January 1, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Live Music)
Sunset Celebration — January 1, 2027 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
Sunset Celebration — January 2, 2027 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
Keller Williams Trio featuring Gibb Droll & Jason Hann — January 2, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Scott Kirby - 36 YEARS OF SONGS AND STORIES with Noah Robertson — January 2, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
Sunset Celebration — January 3, 2027 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
Scott Kirby - 36 YEARS OF SONGS AND STORIES with Noah Robertson — January 3, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
Sunset Celebration — January 4, 2027 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
Ben Harrison — January 5, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
Sunset Celebration — January 5, 2027 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
Brian Patafie (7:00PM) — January 6, 2027 · 7:00 PM (Doors 6:15 PM) · Back Stage Listening Room (Browse group: Community)
Brian Patafie (9:00PM) — January 6, 2027 · 9:00 PM (Doors 8:30 PM) · Back Stage Listening Room (Browse group: Community)
Key West Literary Seminar — January 6, 2027 · San Carlos Institute: An annual gathering of writers and readers, featuring discussions, workshops, and lectures from renowned authors. (Browse group: Arts & Culture)
Sunset Celebration — January 6, 2027 · 5:30pm · Mallory Square: A nightly celebration featuring local artisans, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
Key West Literary Seminar — January 7, 2027 · San Carlos Institute: An annual gathering of writers and readers, featuring discussions, workshops, and lectures from renowned authors. (Browse group: Arts & Culture)
Key West Farmers Market — January 7, 2027 · 1:00pm - 6:00pm · Truman Waterfront: A weekly market featuring local produce, crafts, and artisan goods from Key West and the surrounding areas. (Browse group: Food & Drink)
Brian Patafie — January 7, 2027 · 8:00 PM (Doors 7:00 PM) · Back Stage Listening Room (Browse group: Community)
Key West Art Walk — January 7, 2027 · 6:00pm - 9:00pm · Various galleries on Duval: An evening event where local galleries open their doors for art lovers to explore and enjoy. (Browse group: Arts & Culture)
Key West Literary Seminar — January 8, 2027 · San Carlos Institute: An annual gathering of writers and readers, featuring discussions, workshops, and lectures from renowned authors. (Browse group: Arts & Culture)
Key West Artisan Market — January 8, 2027 · 10:00am - 2:00pm · Higgs Beach: A market featuring local artisans showcasing their crafts, food, and more at Higgs Beach. (Browse group: Food & Drink)
Jim Messina — January 12, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Pearl Jam Night w/ Tony Baltimore at 5:30 & 9:00 — January 12, 2027 · 5:30 PM – 11:00 PM · Green Parrot Bar: Two sets: 5:30-7:00 and 9:00-11:00 Get your flannel & Doc Martens ready! The Green Parrot and Tony Baltimore will host a local-musicians’ tribute to Pearl Jam Photo Credit: Bill Klipp (Browse group: Live Music)
Alice Howe & Freebo — January 13, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
Scott Kirby - 36 YEARS OF SONGS AND STORIES — January 14, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
Alice Howe & Freebo — January 15, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
Key West Half Marathon — January 15, 2027 · 7:00am: A scenic half marathon that takes runners through the beautiful streets of Key West, ending at the beach. (Browse group: Sports)
Kash'd Out w/ A-Mac & The Height — January 16, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Double Duran "The Ultimate Duran Duran Experience" — January 18, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Ben Harrison — January 19, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
The Phil Collins Experience — January 20, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Yacht Rock Revue - Primetime — January 20, 2027 · 7:30 PM (Doors 6:00 PM) · Key West Theater (Browse group: Arts & Culture)
Yacht Rock Revue - Primetime — January 20, 2027 · Doors: 6:00 PM / Show: 7:30 PM · Coffee Butler Amphitheater: Live show at the Coffee Butler Amphitheater (The Key West Amp), Truman Waterfront. (Browse group: Arts & Culture)
Monthly Ukulele Night — January 20, 2027 · 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)
Tom Papa Live — January 21, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Tom Papa Live — January 22, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
Classic Seger: Bob Seger's Greatest Hits Live (9PM) — January 23, 2027 · 9:00 PM (Doors 8:00 PM) · Key West Theater (Browse group: Arts & Culture)
Classic Seger: Bob Seger's Greatest Hits Live (6PM) — January 23, 2027 · 6:00 PM (Doors 5:00 PM) · Key West Theater (Browse group: Arts & Culture)
Scott Kirby - 36 YEARS OF SONGS AND STORIES with Larry Smith — January 28, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
The Expanding Man: An Original Tribute to the Music of Steely Dan & Beyond — January 31, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Live Music)