Upcoming Events

Red Barn Theatre: Ms Holmes & Ms Watson, Apt. 2B
Red Barn Theatre: Ms Holmes & Ms Watson, Apt. 2B
January 28 - February 22, 2025

Red Barn Theatre to Host "Ms. Holmes and Ms. Watson, Apt. 2B" This January Key West, FL – The Red Barn Theatre, a beloved staple in Key West’s vibrant arts community, is set to kick off the new year ...

Coffee Butler Amphitheater: Willie Nelson & Family
Coffee Butler Amphitheater: Willie Nelson & Family
February 17, 2025 7:00 PM

Willie Nelson Returns to Key West: A Night of Legendary Music at Coffee Butler Amphitheater Key West, get ready for a night to remember! The one and only Willie Nelson, a true legend with a career sp...

Waterfront Playhouse: La Cage Aux Folles
Waterfront Playhouse: La Cage Aux Folles
February 26 - March 22, 2025

La Cage Aux Folles at The Waterfront Playhouse Join us at The Waterfront Playhouse from February 26th to March 22nd for La Cage Aux Folles, a Broadway classic that has captivated audiences for decade...

Conch Shell Blowing Contest
Conch Shell Blowing Contest
March 8, 2025 10:00 AM

Blow Into the Fun: The 62nd Annual Conch Shell Blowing Contest! Dive into a beloved island tradition with the Annual Conch Shell Blowing Contest! This quirky and historic event pays homage to the con...

NAS Key West Southernmost Air Spectacular
NAS Key West Southernmost Air Spectacular
March 29 - March 30, 2025

The Southernmost Air Spectacular 2025: A Legacy of Aerial Excellence Continues at NAS Key West Join us on March 29th and 30th, 2025, for a breathtaking display of aerial prowess as the U.S. Navy Flig...

Hemingway Days 2025
Hemingway Days 2025
July 23 - July 27, 2025

Celebrate Ernest Hemingway's enduring legacy and vibrant spirit at Key West’s Annual Hemingway Days 2025, taking place from July 23rd to July 27th on the iconic Duval Street in Key West, FL. This high...

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Upcoming Live Entertainment

Boondocks Grille
Tuesday, Jan 28, 2025

  • 12:00 AM - ERICA SUNSHINE LEE
  • Celtic Conch Public House
    Tuesday, Jan 28, 2025

  • 2:00 PM - Tom Curtis
  • Comedy Key West
    Tuesday, Jan 28, 2025

  • 8:30 PM - Comedy Key West Open Mic
  • El Meson De Pepe's Restaurant and Bar
    Tuesday, Jan 28, 2025

  • 5:30 PM - Mario Vale
  • Hank's Hair of the Dog Saloon
    Tuesday, Jan 28, 2025

  • 1:00 PM - Tony Baltimore
  • 5:00 PM - Sheldon Benton
  • 9:00 PM - Victoria
  • More Live Entertainment

    Latest News

    Florida Keys 2025: A Year of Unforgettable Adventures
    December 20, 2024

    If you're dreaming of a destination that blends tropical beauty with vibrant culture, the Florida Keys should top your 2025 travel list. With a calendar packed full of events ranging from quirky festivals to awe-inspiring spectacles, there’s always s...

    Groove and Sunshine: Key West’s Mile 0 Fest is a Must-See Musical Escape
    December 19, 2024

    Picture this: balmy breezes, turquoise waters, and five days of electrifying music that embodies the heart of Americana and “Red Dirt” soundscapes. Welcome to Mile 0 Fest, where the rhythms of the road meet the soul of the subtropics. Taking place Ja...

    Key West Hosts the Ultimate Flag Football Getaway: The 33rd Annual Kelly McGillis Classic
    December 17, 2024

    A Global Celebration of Sport, Sisterhood, and Sunshine in Key West Pack your bags and head to Key West this January as the island transforms into a vibrant hub of energy, competition, and camaraderie for the 33rd Annual Kelly McGillis Classic Inter...

    Harmony in Paradise: South Florida Symphony Orchestra Brings Timeless Performances to Key West
    December 17, 2024

    Experience the magic of classical music against the backdrop of sun-soaked Key West as the South Florida Symphony Orchestra (SFSO) celebrates its 2025 season with three spectacular performances. Founded 27 years ago in Key West under the visionary le...

    Raise a Toast to Midnight in the Florida Keys: The Legendary Conch Shell Drop at Sloppy Joe’s
    December 12, 2024

    As the final seconds of the year slip away, the heart of Key West pulses with anticipation. Travelers and locals alike fill Duval Street, eagerly awaiting a spectacle that has become as iconic as the southernmost sunsets—Sloppy Joe’s famous Conch She...

    Set Sail for Paradise: Key West Hosts the Thrilling Southernmost Regatta
    December 12, 2024

    Five Days of Competitive Racing, Tropical Vibes, and Unforgettable Experiences Await For sailing enthusiasts and wanderlust-driven travelers, there’s no better way to escape the winter blues than a sun-soaked week in Key West, Florida. From Monday, ...

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