Upcoming Holiday Events in Key West

   Holiday Celebrations

• Wesley House Family Services Holiday Village and BeLighted Bike Ride (December 5): The Wesley House, a non-profit organization addressing child welfare and other family services is hosting their 5th annual holiday village at Key West’s Coffee Butler amphitheater. It features booths with games and activities as well as carnival rides and a bike ride featuring festively decorated bikes. It will run from 5-9 p.m.
• Holiday Historic Inn Tours (December 5 & 12): This annual event offers self-guided tours of Key West’s historic inns specially decorated for the holidays. The tour includes holiday bites and libations.
• Key West Christmas Parade/Old Time Celebration (December 6): This popular parade will run from Truman to Duval Street. It will put you in the holiday spirit with floats, local marching bands and other entertainers and participants in colorful costumes as well as a few surprises. The parade is scheduled to start at 7 p.m.
• Old Town Trolley’s Holiday Sights and Festive Nights Tour (December 8-23): Key West’s well-known trolley offers special holiday tours that explore Key West’s holiday decorations and light displays. Prices for the hour-long tour start from $37.86
• Gay Key West Holiday Lights Trolley Tour (December 13): Key West Business Guild is repeating their gay holiday trolley tour after a positively received debut last year. They suggest you get decked out in your holiday best and tour Key West’s “fabulous” holiday displays. It is scheduled to start at 7 p.m. from Bobby’s Monkey Bar.
• A Positive Step 5K Rudolph Red Nose Run (December 13) This holiday run will start at 8 a.m. from the Southernmost Beach Cafe on Duval Street. Participants are encouraged to wear festive Pj’s or other holiday attire.
• Holiday Classic Car Show & Toy Drive (December 21): This car show featuring classic cars is sponsored by the Florida Keys Southernmost Car Club. It will take place from 11 a.m. to 3 p.m.  at the Conch Republic Seafood Company parking lot on the Harbor Walk of Lights at Greene St. They are requesting an unwrapped toy to benefit the Monroe County Domestic Abuse Shelter.
• Christmas Brunch Sails (December 25): Two ships offer Christmas brunch sailing experiences. One is the Schooner America 2.0 Christmas Day Brunch Sail, and the other is aboard the Argo Navis, a luxury catamaran.
• Key West Artisan Market (November 30, December 14, 21 & 28): This artisan market takes place on certain Sundays between October and April. It features local craft artisans as well as food options.

     New Year’s

• The Conch Shell Drop at Sloppy Joe’s:  This ball drop experience at a bar made famous by Ernest Hemingway s in its 32nd year. Hence, its name, at midnight they drop a huge lit up conch shell.
• The Red Shoe Drop at Bourbon St. Pub: This dropping of a drag queen in a huge red sparkling high heel has been featured yearly on CNN. It is also a fabulous way to ring in the new year.
• The Lowering of the Pirate Wench at Schooner Wharf Bar: This bar offers a popular New Year’s Eve waterfront celebration featuring live music, a cannon blast and the lowering of the “Pirate Wench” from the mast of a tall ship.