Celebrate The Holidays In Key West

If you are looking to spend the holidays in a LGBTQ-friendly destination, Key West, Florida offers a plethora of exciting things to do and experience. Festivities kick off on Wednesday, Nov. 27 with a sunset illumination of the Harbor Walk of Lights at the Key West Historic Seaport. This Christmas display is the perfect way to get into the holiday spirit and is a great way to spend an evening with family and friends ahead of Thanksgiving. 

Events continue throughout the Keys into December. Highlights include the Holiday Party Trolly on Wednesday, Dec. 11. Grab tickets for you and your party and enjoy a one to two hour ride to see beautiful holiday light displays with a couple special stops for refreshing drinks. 

The party continues into Friday with the Key West Annual Holiday Concert & Bazaar at the Key West Museum of Art and History on Friday, Dec. 13. Enjoy food and drinks, a holiday light show designed by the Key West High School, and shop for gifts from some of the region’s finest artisans. The best part? This event is free and open to the public. Selections include jewelry, textiles, home decor, clothing, stationery, confections, and more.

Also starting on Dec. 13 is the Waterfront Winter Wonderland. This family-experience continues through Dec. 28 and transforms the grounds of the Coffee Butler Amphitheater, overlooking Key West Harbor, into a glowing winter wonderland. Enjoy an ice skating rink, festive light displays, carnival rides (including a romantic ferris wheel), a Christmas train and inflatable snow globes, and musical performances. Bring the kids or engage your inner child! And don’t miss when Santa himself stops in. 

On Dec. 14 the Annual Schooner Wharf Bar Lighted Boat Parade returns for its 33rd year. At 8 p.m. spectators can watch from the docks as boats and sailing vessels decked out in holiday displays and lights compete for best decor. 

Key West bars and restaurants are always hosting amazing LGBTQ+ friendly events including drag shows, open mics and live music performances, all you have to do is walk down the main strip to find something lively. 

To finish off the year on the right foot, the New Year’s Eve Red Shoe Drop is a can’t miss event at Bourbon Street Pub in Key West. For 25 years, famous drag queen Sushi was dropped from the roof of the bar surrounded by extensive light displays, twinkling all the way down to celebrate a fresh start. But last year a new drag queen filled the shoe, literally. This New Year’s celebration is a bucket list item for LGBTQ+ travelers and the ideal place to cap off 2024.