Waterfront Playhouse: La Cage Aux Folles

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: A Historic Florida Keys Tradition The 62nd Annual Conch Shell Blowing Contest celebrates a cherished Florida Keys tradition with a blend of history and creativity. Hosted...

Comedy Key West | John Caparulo

John Caparulo Live Comedy in Key West Likely To Sell Out! Special Event features acclaimed comedian John Caparulo performing live in Key West. The event runs over four consecutive nights: Thu, Mar 13...

Irish Kevin's 5k/10k Shamrock Shuffle

Key West Shamrock Shuffle 2025 The 12th Annual IK Shamrock Shuffle in Key West is a must-attend charity race event for St. Paddy's enthusiasts. Participants can choose from a 5K Run, 5K Walk, 10K Run...

NAS Key West Southernmost Air Spectacular

Experience the Southernmost Air Spectacular with the Blue Angels at NAS Key West The Southernmost Air Spectacular 2025 returns on March 29th & 30th, 2025 at NAS Key West. This family-friendly air...

Conch Republic Independence Celebration

Celebrate the Conch Republic’s 43rd Anniversary in Key West The 43rd Annual Conch Republic Independence Celebration 2025 honors a unique legacy rooted in the founding of the Conch Republic on April 2...

Boondocks Grille

Captain Tony's Saloon

Comedy Key West

Green Parrot Bar Webcam

Hank's Hair of the Dog Saloon

Hemingway Distillery

Fishing & Key West Live Music in May

Florida Keys Fishing & Key West Live Music: A May Extravaganza Experience the ultimate May getaway in Key West with a dynamic fusion of Florida Keys fishing and Key West live music. Held at the historic Key West Theater (512 Eaton Street, Key We...

Florida Keys 2025: A Year of Unforgettable Adventures

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

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

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

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

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...