Sunset Celebration at Mallory Square

Key West's Sunset Celebration: A Must-Experience Event at Mallory Square Every evening, just as the sun begins its slow descent into the Gulf of Mexico, Mallory Square in Key West transforms into a l...

Waterfront Winter Wonderland

Discover the Magic of Key West’s Waterfront Winter Wonderland! If you're dreaming of a holiday getaway that adds a touch of enchantment to your Key West experience, look no further than the Waterfron...

Comedy Key West: Jim Florentine

Get ready to laugh until your cheeks hurt, because comedy legend Jim Florentine is taking the stage in Key West! Known for his razor-sharp wit and a comedic style that’s as bold as it is hilarious, Ji...

Running of the Elves 5k Run/Walk & Jingle Bell Mile

Get Your Holiday Cheer On with the Running of the Elves 5K and Jingle Bell Mile! Join the festive fun at the 1st Annual Running of the Elves 5K and Jingle Bell Mile on Saturday, December 21, 2024, at...

New Year's Eve Lowering of the Pirate Wench

Celebrate the New Year in true Schooner Wharf style with the annual Lowering of the pirate wench down the mast of the Schooner America 2.0 at midnight. Enjoy live music through the afternoon and eveni...

New Year's Eve: Conch Shell Drop at Sloppy Joe's

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. Travele...

Boondocks Grille

Hog's Breath Saloon Webcam

Irish Kevin's Webcam

Lagerheads Beach Bar & Watersports

Margaritaville Cafe

Schooner Wharf Bar & Grill Webcam

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...

Set Sail for Paradise: Key West Hosts the Thrilling Southernmost Regatta

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, ...

Literary Paradise: Key West Explores the Ties That Bind at Annual Seminar

Escape to the sun-kissed streets of Key West this January and immerse yourself in the power of storytelling at the 42nd Annual Key West Literary Seminar. From January 9–12, 2025, literary enthusiasts will gather at the historic San Carlos Institute t...

Chase the Sun: Key West Half Marathon Beckons Runners to a Tropical Paradise

Why You’ll Love This RacePicture this: a crisp January morning with the gentle warmth of the subtropical sun on your shoulders, the sound of waves lapping against the shore, and the vibrancy of Florida’s southernmost island all around you. That’s the...