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.

Ultimate Adventure activities

Special Offer For Florida Residents

Now – December 18, 2020

There’s never been a better time for Sunshine State locals to discover an adventure in their own backyard! Florida Residents Save Big on some of our most exciting tours we offer here in paradise (aka Key West, Florida). Who doesn’t want to get some fresh air, sunshine and Ultimate Savings?! Use the code FLORIDA when booking your next trip before December 19, 2020, and explore the fun of the Key West waters above and below sea-level.

Old Town Trolley with holiday lights in Key West

Holiday Tours on the Trolley 

Select Nights from December 4th – 23rd

Ever seen a palm tree decorated with holiday lights? Celebrate this festive time of year with a tour as unique as Key West. Conch Tour Train and Old Town Trolley offer Holiday Lights Tours that guide you around Key West to see the island dressed to its best in lights and décor. 2020 dates are December 4-23, 2020. Conch Tour Train’s version departs from Key West High School. Old Town Trolley’s departs from Mallory Square. Each one-hour tour includes special holiday lights glasses and views of the most elaborately decorated homes, buildings and neighborhoods. Even though these tours take place in December, you want to purchase tickets now. Space is limited and these special trolleys and trains will fill up quick.

Key West Triathlon

December 5th

The annual Key West Triathlon brings 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.

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.

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.

Image of Key West Fury catamaran

Key West Private Catamaran Charters in Paradise

Discover the pristine blue waters of Key West aboard your very own private charter. We offer a fleet of high-performance catamarans that can transport your party on a private boat excursion of your choice for a truly unforgettable experience. Private Charters are completely customizable for your group and can include catering, full bar, live bands and picture packages. Whether you’re looking for a relaxing full-day on the water sipping your favorite cold beverage, or an adventurous half-day excursion, our team is prepared to help you plan the perfect day in paradise!

Monthly Artisan Market

CANCELLED IN 2020

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.

Annual Key West House & Garden Tours

CANCELLED IN 2020

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.

Sail with Santa Sunset Sail with Fury Water Adventures

Fury’s Annual Sunset Sail with Santa Benefiting Wesley House

CANCELLED IN 2020

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.

Key West Holiday Parade

CANCELLED IN 2020

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.

Holiday Concert & Bazaar

CANCELLED IN 2020

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!

Last Updated 11/24/2020