Best things to do in Key West in December 2023
It’s the most wonderful time of the year, and this December’s events reflect exactly that.
From celebrating New Year’s Eve on a sub-tropical island, to eating fresh seafood and watching a parade full of Dashchunds, this December in Key West will be quirky and cultural, as it should be.
1. Run A Triathlon
The Key West Triathlon, now in it’s 11th year, attracts athletes from all over to compete in paradise. With 1,000 contestants, it’s a “big race on a little island.” The best part? The swimming portion in the ocean is much warmer compared to other races around the world this month. The races happen Sunday, December 10th.
2. Join The Lighted Bike Parade
The Wesley House Family Services’ Annual Holiday Village & BeLighted Bike Ride is the premiere family-friendly event to kick off the Holiday Season. The fun begins at 4 pm on Friday, December 2nd at the Coffee Butler Amphitheater in Truman Waterfront Park, Key West. The Holiday Village runs from 4 – 8 pm and the BeLighted Bike Ride leaves from the Amphitheater at 8 pm and follows the same route as the Fantasy Fest parade, up Whitehead, and down Duval Streets.
The Holiday Village is the family-friendly pre-party to the bike ride, featuring over 20 community booths offering games, goodies, and crafts for the kids, DJ, food trucks, and photos with Santa! Enter the “best bike” contest at 7 and then cruise Duval St. at 8 pm on your ultra-lighted bike! Costumes are encouraged! Purchase tickets here!
3. Coast Is Clear Music Festival
Coast is Clear Music & Arts Festival Come enjoy numerous amazing musicians at numerous iconic venues in the historic Bahama Village Neighborhood of downtown Key West. November 30-December 3. Dance, drink and be merry! Tickets sold here!
4. Watch The Lighted Boat Parade
The family-friendly annual boat parade is a locals favorite. Watch as tall ships, yachts, row-boats and everything in between float along the historic seaport decked out in the holiday spirit! December 9th @ 8pm.
5. Get in the Christmas “Spirit” on a Cocktail Crawl
Our tour encompasses a lot more than just drinks. Discover the local haunts and how the Hemingway Daiquiri was invented, as we walk through historic neighborhoods from restaurant to restaurant.
6. Annual Holiday Bazaar
Join us for the highly anticipated Annual Custom House Holiday Concert & Bazaar on Friday, December 8, from 5 pm to 9 pm.
The event takes place on the porch and in the street in front of the gorgeous and historical Customs House located at 281 Front St and will feature not only vendors set up for holiday shopping, but also food and drinks, musicians, a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House.
More info here
7. 10th Annual Parade of Paws
Join the Florida Keys SPCA at the Higgs Beach Dog Park on December 9th from 10 a.m. – 2 p.m. for a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar and the crowning of the 2023 Royal Court. Enjoy pictures with Santa, sloppy kisses at the Smooch-a-Pooch booth, fun raffles and a dog parade where all pups are welcome to strut their stuff around the beach! Costumes encouraged! All proceeds from the event will benefit the homeless animals of the Middle and Lower Keys.
8. Waterfront Winter Wonderland
Don’t let our warm, balmy temperatures fool you, we love the Holidays in Key West! This December, the Coffee Butler Amphitheater at the Truman Waterfront Park will transition into a Key West Winter Wonderland for an all ages, family friendly holiday experience. There will be vendors for food, drink and gifts as well as attractions, rides, light displays and best of all – a custom ice skating rink for amateurs and pros alike. You can enjoy this wonderland from December 15-30.
More details located here
BONUS! Celebrate A Tropical New Year’s Eve
This weird year isn’t officially over until a drag queen drops down in a red stiletto. Other drops around town include a wench, conch shell, cuban cigar, and key lime wedge. But the icing on the cake is drinking champagne in 75 degree weather!