There’s nothing quite like the holidays in Key West. Where else can you enjoy warm winter weather, water sports and palm trees wrapped in twinkling holiday lights? Whether you’re here during one of the big December holidays or simply taking an end of the year vacation, there are plenty of things to do in Key West in December.

Key West Holiday Parade

December 7th

October’s Fantasy Fest parade might get all the attention, but Key West also hosts a festive, family friendly holiday parade every December. With floats and marching groups representing local churches, civic organizations, businesses and schools, it’s a fantastic way to celebrate the holiday season. Find a spot to watch on the main drag of Duval Street or anywhere along the parade’s route on Truman Street.

Old Town Trolley with holiday lights in Key West

Holiday Tours on the Trolley 

Select Nights from December 6th-23nd

Key West might not turn into a snowy winter wonderland in December, but that doesn’t mean the residents don’t go all out with the holiday decor. Hop aboard Old Town Trolley or Conch Tour Train for their annual holiday lights tours. Ride around town oohing and aahing at twinkling lights, garlands, props and other decorations. And these 60 minute tours aren’t just about the sights, be sure to grab a few cookies and a glass of cider for the road! This annual holiday tradition is a hit with every member of the family and is sure to put you in the holiday spirit.

Key West Triathlon

December 7th

The annual Key West Triathlon brings 1,000 athletes to the southernmost point for this inspiring competition that includes running, cycling and swimming. Key West’s mild winter temperatures make for the perfect conditions both on land and in the water. Those who register can choose between Olympic and Sprint distances.

Sail with Santa Sunset Sail with Fury Water Adventures

Fury’s Annual Sunset Sail with Santa Benefiting Wesley House

December 12th

For subtropical holiday cheer, join us aboard our annual Sunset Sail with Santa benefiting Key West’s Wesley House. Children 12 and under sail for free and we ask for a minimum $25 donation from adult participants. Trek the Key West waters with us and enjoy complimentary beer, wine, champagne and holiday snacks. And, of course, Santa will be there! It’s fun for the whole family and benefits a great cause.

Monthly Artisan Market

December 1st, 15th & 29th

For those looking to do some shopping, head on over to the Restaurant Store on Eaton Street for the monthly Artisan Market. This month’s theme is Holiday Shop Local. Cruise the vibrant, open-air market filled with artists, chefs, authors, craftspeople and performers. Browse delectable treats such as fresh produce, baked goods, flowers, craft beer and wine.

Holiday Concert & Bazaar

December 18th

This inaugural event held at the Custom House Museum is sure to put you in the holiday spirit! Join Key West’s finest artisans, musicians and choirs for a night of family-friendly fun. And what would a holiday festival be without a flashy light show? Do some last minute gift shopping while browsing hundreds of unique options while listening to live music, sampling delicious food and sipping on libations. This event is free to the public, including Santa’s helpers!

Sailboat in the ocean with snowflakes

Christmas Ultimate Adventure

December 25th

In Key West for Christmas? Start a unique family tradition and enjoy Christmas at sea with Fury’s Ultimate Adventure trip. This full day trip includes breakfast and a special holiday lunch as well as unlimited beer and wine. You’ll go snorkeling, parasailng, jet skiing, ride banana boats and more. Enjoy spending time with your loved ones while taking in Key West’s amazing December weather.

Annual Key West House & Garden Tours

December 27th & 28th

Part of Key West’s inherent charm rests in its lovely homes and Victorian-style architecture. During the Key West House & Gardens Tours, enjoy a self-guided exploration through some of Key West’s most beautiful homes while they’re all dressed up for the holidays. This casual and festive event is presented by the Old Island Restoration Foundation.

Fury sail boat with beautiful orange sunset as background

New Year’s Eve in Key West

December 31st

Key West is always counted among the best places in the country to ring in the New Year—and for good reason. With warm, subtropical temperatures and a festive party atmosphere, it’s all laid back good fun here on New Year’s Eve. Start your evening with the last sunset sail of the year aboard one of our catamarans and then hit the town’s multiple bars and restaurants. And don’t forget about the various countdowns to midnight, all of which are done in true Key West style. You can watch the Conch Drop from Sloppy Joe’s, the Stiletto Drop from Bourbon Street Pub or the Wench Drop at Schooner Wharf.

Last Updated 06/17/2020