'A Positive Step' 5k Rudolph Red Nose Run
Join the Festive Fun: 15th 'A Positive Step' 5k Rudolph Red Nose Run in Key West Get ready to don your festive holiday jammies and step into the magic of the 15th 'A Positive Step' 5k Rudolph Red Nos...
Breakfast with Santa at The Hard Rock Cafe
Come along for Breakfast with Santa on December 16th and 17th, from 9 am to 12 pm! Enjoy a delightful Special Breakfast Buffet, complemented by Unlimited Mimosas. Engage in fun with Donut Decorating ...
Holiday Classic Car Show
See classic cars from a variety of eras at the official show of the Florida Keys Southernmost Car Club, and choose a People’s Choice winner with your votes. Located at the Conch Republic Seafoo...
Pictures with Santa at The Perry Hotel
Capture the magic of the holiday season with Santa at The Perry. Join us for a festive tropical photoshoot with Ol' Saint Nick himself! Bring the family and create unforgettable memories with our jol...
Holiday Train Fundraiser by Fringe Theatre
HOLIDAY TRAIN December 17, 2023 -- -- The Gardens Hotel It's our first fundraiser of the season and a crowd favorite! Check-in at 7pm at the beautiful Gardens Hotel and enjoy a tasty beverage at the G...
Ben Harrison
Experience the Musical Magic of Ben Harrison Live! Prepare to be swept away on a one-of-a-kind musical journey as the charismatic Ben Harrison graces the stage at the Key West Theater's Back Stage Li...
Red Barn Theatre: A Tuna Christmas
Red Barn Theater : Discover the Heartwarming Hilarity of "A Tuna Christmas" in the Lone Star State Nestled deep within the Texan landscape, in the quaint confines of the third-smallest ...
Key West Theater: Peter Mayer--Stars & Promises Christmas Tour
Ladies and gentlemen, prepare to be immersed in a world of musical excellence as we introduce Peter Mayer, a multifaceted artist who has left an indelible mark on the music industry. With a career spa...
Microparty: Electric Blue Yonder at The Studios Of Key West
A traveling troupe of intrepid space folk explorers, Electric Blue Yonder (EBY) examines the mysteries of the universe and reports their findings through song. The popular touring band has graced Key ...
Pilar Rum Tasting at Oceans Edge
Pilar Rum Tasting Key West is known for its rum! Taste some of the best from Pilar Rum at deliciously educational tastings on December 22.
The Marker 4th Annual Holiday Cookie Throw Down
Break out your best cookie recipe and submit your creation to the 4th annual Holiday Cookie Throw-down!! December 24th at 12pm. Resort guests will be your judges! Prizes will be awarded! You must RSV...
Jazz in the Gardens
Sway to the Rhythms of Jazz : Gardens of Key West When the sun begins to dip below the horizon, and the balmy evening air embraces you in its gentle warmth, there's no better place to...