Key West Festivals

Browse Hey Key West's current festivals event grouping, with dates, venues, and details.

  • TUTU SALSA SESSIONS — October 19, 2026 · Southernmost Beach Resort: Tuesday, October 20, 2026. Celebrate one of Fantasy Fest’s most colorful traditions during Tutu Tuesday at Southernmost Beach Café, where beachfront drinks give way to an evening of salsa dancing, festive attire, (Browse group: Festivals)
  • The Greatest Hits Pool Party — October 19, 2026 · Winslow's Bungalows: Tuesday, October 20, 2026, from noon to 4 p.m. Dress like an icon and sing like a legend during the Greatest Hits Pool Party at Winslow’s Bungalows, part of the 2026 Fantasy Fest celebration in Key West. (Browse group: Festivals)
  • The Beatle Band at 5:30, 9:00 & 11:00 *Offical Fantasy Fest Event — October 19, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Tony Baltimore, Chris Thomas, Hiram Garzaro, and Oren Polak, re-create a Fab Four Show with "THE BEATLE BAND, All You Need is Love" with shows at 5:30, 9:00 and 11:00pm. Their past Beatle Tribute Shows had Parrot patrons swinging from the rafters as they danced, laughed, and sang along to a set-list pulled from decades of Lennon-McCartney hits. Photo Credit: Bill Klipp (Browse group: Festivals)
  • Fantasy Fest — October 21, 2026 · Duval Street: A 10-day festival featuring themed parties, parades, and costume contests, celebrating the spirit of Key West. (Browse group: Festivals)
  • Goombay Festival — October 22, 2026 · Bahama Village: A vibrant celebration of Bahamian culture with music, food, and arts in the heart of Bahama Village. (Browse group: Festivals)
  • FUNK IT UP Party with Trae Pierce & The T-Stones at 5:30, 9:00 & 11:00 *Official Fantasy Fest Event — October 22, 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 Four-time Grammy Award winning funk master Trae Pierce and his band the T-Stones return to our stage for a funky good weekend. Trae and his band members consider the Parrot stage as merely their launching pad as they swarm into the crowd with their infectious beats and can't-stay-in-your-seat dance-moves. Pierce gets audiences fired up with his funky talk box versions of 2Pac’s “California Love,” Phil Collin’s “In the Air Tonight,” and “24K Magic” by Bruno Mars while The T-Stones’ lead vocalist Pierce’s son, Ray Pierce, adds a hip-hop flavor to the music. Speaking of flavor, fun fact: Ray has his own famous connections having been Flava Flav’s roommate in California for several years... (Browse group: Festivals)
  • Key West Film Festival — November 9, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events with filmmakers. (Browse group: Festivals)
  • Key West Film Festival — November 10, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events with filmmakers. (Browse group: Festivals)
  • Key West Film Festival — November 11, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events with filmmakers. (Browse group: Festivals)
  • Key West Film Festival — November 12, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events with filmmakers. (Browse group: Festivals)
  • The Resolvers at 5:30, 9:00 & 11:00 — November 13, 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 The Resolvers Bring “Big Band Reggae” to Green Parrot. Named the Best Reggae band of 2013 by The Ft Lauderdale New Times, The Resolvers draw influences from classic Jamaican Reggae, Rocksteady, and Ska along with American Rock, Jazz, Funk, and Soul. Their live show has been described as explosive with up to 10 musicians on stage, including a full horn section, and led by the powerful brother & sister duo of Ojay & Sahara Smith on lead vocal roles. The Resolvers play in the style they coined “Big Band Reggae” combining classic jamaican roots and lively new orleans stylings. Siblings Ojay & Sahara Smith (son and daughter of Ernie Smith) both take turn on lead vocals roles and the band features a 4 piece horn section. Their show has been described as “explosive” and “must see”, and the band has gained the reputation as a premier reggae act. The Resolvers have shared the stage with The Wailers, Julian Marley, Stephen Marley, Damian Marley, Kymani Marley, Inner Circle, English Beat, Yellowman, Matisyahoo, Lee ‘Scratch’ Perry, Mishka along many other world renowned acts in major International festivals such as Marley Fest, Jamaican Jazz & Blues Fest, Sun Fest, Aura Music & Arts Fest, Dub Fest and more. (Browse group: Festivals)
  • Key West Film Festival — November 13, 2026 · Tropic Cinema: An annual celebration of independent film featuring screenings, panels, and special events with filmmakers. (Browse group: Festivals)
  • The Resolvers at 5:30, 9:00 & 11:00 — November 14, 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 The Resolvers Bring “Big Band Reggae” to Green Parrot. Named the Best Reggae band of 2013 by The Ft Lauderdale New Times, The Resolvers draw influences from classic Jamaican Reggae, Rocksteady, and Ska along with American Rock, Jazz, Funk, and Soul. Their live show has been described as explosive with up to 10 musicians on stage, including a full horn section, and led by the powerful brother & sister duo of Ojay & Sahara Smith on lead vocal roles. The Resolvers play in the style they coined “Big Band Reggae” combining classic jamaican roots and lively new orleans stylings. Siblings Ojay & Sahara Smith (son and daughter of Ernie Smith) both take turn on lead vocals roles and the band features a 4 piece horn section. Their show has been described as “explosive” and “must see”, and the band has gained the reputation as a premier reggae act. The Resolvers have shared the stage with The Wailers, Julian Marley, Stephen Marley, Damian Marley, Kymani Marley, Inner Circle, English Beat, Yellowman, Matisyahoo, Lee ‘Scratch’ Perry, Mishka along many other world renowned acts in major International festivals such as Marley Fest, Jamaican Jazz & Blues Fest, Sun Fest, Aura Music & Arts Fest, Dub Fest and more. (Browse group: Festivals)
  • Pirates in Paradise — November 19, 2026: A week-long festival celebrating Key West's pirate history with parades, music, and family-friendly activities. (Browse group: Festivals)
  • Pirates in Paradise — November 20, 2026: A week-long festival celebrating Key West's pirate history with parades, music, and family-friendly activities. (Browse group: Festivals)
  • Pirates in Paradise — November 21, 2026: A week-long festival celebrating Key West's pirate history with parades, music, and family-friendly activities. (Browse group: Festivals)
  • Ajeva at 5:30, 9:00 & 11:00 — November 27, 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 AJEVA (ah-JAY-vuh) is a Progressive Funk, five piece powerhouse hailing from St. Petersburg, FL. They spread their message of peace, unity and higher consciousness through music with infectious grooves and driving energy. Composed of Reed Skahill (vocals), Taylor Gilchrist (bass), Travis Young (drums), Lyndon Thacker (guitar/keyboards) and Michael Nivens (guitar), Ajeva has been playing all over the Eastern U.S. since March 2013. These gentlemen pride themselves on providing the ultimate voyage for your earholes, with an enthralling live show that will keep you watching and listening. (Browse group: Festivals)
  • Ajeva at 5:30, 9:00 & 11:00 — November 28, 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 AJEVA (ah-JAY-vuh) is a Progressive Funk, five piece powerhouse hailing from St. Petersburg, FL. They spread their message of peace, unity and higher consciousness through music with infectious grooves and driving energy. Composed of Reed Skahill (vocals), Taylor Gilchrist (bass), Travis Young (drums), Lyndon Thacker (guitar/keyboards) and Michael Nivens (guitar), Ajeva has been playing all over the Eastern U.S. since March 2013. These gentlemen pride themselves on providing the ultimate voyage for your earholes, with an enthralling live show that will keep you watching and listening. (Browse group: Festivals)
  • Ajeva Soundcheck Set — November 29, 2026 · 5:30 PM – 7:00 PM · Green Parrot Bar: One 90-minute set: 5:30-7:00 AJEVA (ah-JAY-vuh) is a Progressive Funk, five piece powerhouse hailing from St. Petersburg, FL. They spread their message of peace, unity and higher consciousness through music with infectious grooves and driving energy. Composed of Reed Skahill (vocals), Taylor Gilchrist (bass), Travis Young (drums), Lyndon Thacker (guitar/keyboards) and Michael Nivens (guitar), Ajeva has been playing all over the Eastern U.S. since March 2013. These gentlemen pride themselves on providing the ultimate voyage for your earholes, with an enthralling live show that will keep you watching and listening. (Browse group: Festivals)
  • 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)
  • Key West Songwriters Festival — March 1, 2027: An annual celebration of songwriters featuring performances, workshops, and showcases throughout the island. (Browse group: Festivals)
  • Key West Songwriters Festival — March 4, 2027: An annual celebration of songwriters featuring performances, workshops, and showcases throughout the island. (Browse group: Festivals)
  • Key West Songwriters Festival — March 6, 2027: An annual celebration of songwriters featuring performances, workshops, and showcases throughout the island. (Browse group: Festivals)
  • Key West Songwriters Festival — March 7, 2027: An annual celebration of songwriters featuring performances, workshops, and showcases throughout the island. (Browse group: Festivals)
  • Key West Songwriters Festival — March 8, 2027: An annual celebration of songwriters featuring performances, workshops, and showcases throughout the island. (Browse group: Festivals)
  • Magic of the Conch Republic — April 18, 2027 · 7:00 PM (Doors 6:00 PM) · Key West Theater (Browse group: Festivals)
  • Conch Republic Independence Celebration — April 23, 2027 · Duval Street: A quirky celebration of Key West's independence from the United States, featuring parades, parties, and various festivities. (Browse group: Festivals)
  • Key West Songwriters Festival — May 3, 2027: An annual festival celebrating the craft of songwriting with performances by renowned songwriters and artists. (Browse group: Festivals)
  • Key West Songwriters Festival — May 4, 2027: An annual festival celebrating the craft of songwriting with performances by renowned songwriters and artists. (Browse group: Festivals)
  • Key West Songwriters Festival — May 5, 2027: An annual festival celebrating the craft of songwriting with performances by renowned songwriters and artists. (Browse group: Festivals)
  • Key West Songwriters Festival — May 6, 2027: An annual festival celebrating the craft of songwriting with performances by renowned songwriters and artists. (Browse group: Festivals)
  • Key West Songwriters Festival — May 7, 2027: An annual festival celebrating the craft of songwriting with performances by renowned songwriters and artists. (Browse group: Festivals)
  • Key West Pride — June 1, 2027: A week-long celebration of the LGBTQ+ community featuring parades, parties, and various events throughout Key West. (Browse group: Festivals)
  • Key West Pride Parade — June 10, 2027 · 5:00pm · Duval Street: Join the colorful parade celebrating diversity and inclusion in the heart of Key West. (Browse group: Festivals)
  • Hemingway Days — July 21, 2027 · Sloppy Joe's Bar: A celebration of Ernest Hemingway's life and work, featuring literary readings, a look-alike contest, and more. (Browse group: Festivals)