February 2027 Key West Events & Festivals

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

  • Sunset Celebration — February 1, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Sunset Celebration — February 2, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Key West Farmers Market — February 3, 2027 · 1:00pm - 6:00pm · Truman Waterfront: A weekly market featuring fresh produce, local goods, and artisan products from the Florida Keys. (Browse group: Food & Drink)
  • Key West Art Walk — February 3, 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)
  • Sunset Celebration — February 3, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Ben Harrison — February 3, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • The Massacoustics — February 3, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Key West Tropical Forest & Botanical Garden Plant Sale — February 4, 2027 · 10:00am - 4:00pm · Key West Tropical Forest & Botanical Garden: A sale featuring a variety of plants native to the Florida Keys, perfect for gardening enthusiasts. (Browse group: Community)
  • The Massacoustics — February 4, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Sunset Celebration — February 4, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Sunset Celebration — February 5, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Key West Artisan Market — February 5, 2027 · 10:00am - 2:00pm · Higgs Beach: A market featuring local artisans showcasing their crafts, food, and unique products. (Browse group: Food & Drink)
  • Sunset Celebration — February 6, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Pete Yorn Solo Acoustic: 25th Anniversary of musicforthemorningafter — February 6, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Live Music)
  • Scott Kirby - 36 YEARS OF SONGS AND STORIES with Gabriel Donohue — February 8, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Scott Kirby - 36 YEARS OF SONGS AND STORIES with Emily Randle — February 9, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Key West Farmers Market — February 10, 2027 · 1:00pm - 6:00pm · Truman Waterfront: A weekly market featuring fresh produce, local goods, and artisan products from the Florida Keys. (Browse group: Food & Drink)
  • In Cahoots — February 10, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Sunset Celebration — February 10, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Who's Bad: The World's #1 Michael Jackson Tribute — February 11, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Sunset Celebration — February 11, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • In Cahoots — February 11, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Sunset Celebration — February 12, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • A Tribute to the Songs of Pat Dailey, with Ray Fogg & Reese Dailey and Special Guests — February 13, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Ben Harrison — February 16, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Key West Farmers Market — February 17, 2027 · 1:00pm - 6:00pm · Truman Waterfront: A weekly market featuring fresh produce, local goods, and artisan products from the Florida Keys. (Browse group: Food & Drink)
  • Sunset Celebration — February 17, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • John Frinzi & Aaron Scherz — February 18, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Sunset Celebration — February 18, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • John Frinzi & Aaron Scherz — February 19, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Sunset Celebration — February 19, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Sunset Celebration — February 20, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Sunset Celebration — February 21, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Sunset Celebration — February 22, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Sunset Celebration — February 23, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • DMTB: The Dave Matthews Tribute Band- Burnin’ One Tour — February 24, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Live Music)
  • Sunset Celebration — February 24, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • Scott Kirby - 36 YEARS OF SONGS AND STORIES with Matt Backer — February 25, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Sunset Celebration — February 25, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf of Mexico. (Browse group: Live Music)
  • The Jayhawks — February 25, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)