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Best things to do in Key West in December 2022


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 December 11th.


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

Enjoy a wonderful weekend under the tropical island sun at the East Martello Fort – One of Key West’s old civil war forts turned music venues for the Coast is Clear Music & Arts Festival Dec 1-4. Dance, drink and be merry! Tickets sold here!

4. See the Nutcracker Key West-style

A naughty and spirited two-actreverie, inspired by the famed Tchaikovsky holiday classical “The Nutcracker” ballet, is sure to bring laughter to Key West’s holiday festivities. Clara, a young ingénue, celebrates the season with one to many sugar rum cherry cocktails. That night she dreams of sword fights and sailors and a world unlike any other in the “Land of Libations”. The show stars Tatah DuJour, Moana Amour, Jenna Beth and Auroura Natrix. December 19th. Click here for tickets 


5. 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 10th @ 8pm.


6. 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.

7. Mingle & Jingle


Sip, shop, and stroll the stores, studios and galleries inside the historic Shops at Mallory (formerly Coast Guard Building/Clinton Square Market Mall, next to The Custom House). Shop the holidays and everyday from your neighbors — the small businesses of the Key West community appreciate you and welcome you to come mingle and get to know them.

8. 9th Annual Parade of Paws

Join the Florida Keys SPCA at the Higgs Beach Dog Park 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 2022 Royal Court.  Enjoy pictures with Santa, sloppy kisses at the Kiss A Bull 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.


BONUS! Celebrate A Tropical New Year’s Eve

Photo // The Key West Citizen, Rob O’Neal MIAMI HERALD OUT

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!