Habitat for Humanity hosted a Las Vegas-themed silver anniversary party last year at the Cheeca Lodge & Spa in Islamorada. The Kentucky Derby is the theme for this year’s Cocktail Party on March 8 at Cheeca Lodge. CONTRIBUTED

Gear up for a night of Southern charm and equine elegance as Habitat for Humanity of the Upper Keys presents its 21st annual cocktail party with a Kentucky Derby theme.  

Set for Friday, March 8 at 6:30 pm at Cheeca Lodge & Spa in Islamorada, this year’s celebration promises a twist of Kentucky Derby glamor. A VIP pre-party will take place on the grand lawn adjoining the lodge.

The cocktail party will bring together the sophistication of the Derby with the laid-back charm of the Florida Keys. Guests will be transported to a world of mint juleps, Southern hospitality and the thrill of the race. 

What to Expect

  • Dress to impress: Guests are encouraged to don their most dashing Derby attire. For ladies, that includes those fabulous hats and fascinators, and for gentlemen, seersucker and bow ties. Prizes will be awarded for the best ladies’ hat or fascinator, best gentlemen’s bowtie and best-coordinated couple.
  • Southern culinary delights: Indulge in an array of Southern-inspired delicacies that pay homage to the flavors of the Derby, from bourbon-infused treats to classic Southern comfort food.
  • Live entertainment: Dance into the night with tunes that blend the best of Southern tradition with the laid-back vibes of the Florida Keys.
  • Live and silent auctions: A live auction will feature exclusive items and experiences. A silent auction will include art, jewelry, fishing/diving adventures, restaurant meals and more. All proceeds will go toward Habitat’s mission of building homes, communities and hope.
  • Gambling tables: Guests can try their hand at blackjack, roulette, craps and more, all while raising funds for affordable housing.  

The VIP pre-party will feature bourbon tasting and appetizers in an open-air setting along with reserved cocktail party seating. Tickets are limited. The cocktail party includes various food stations, unlimited beer and wine, access to the gaming tables and auctions. A limited number of reserved tables are available. 

Tickets are available at

The presenting sponsors are First Horizon Bank, Florida Keys Board of Realtors and American Caribbean Real Estate.