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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 Dachshunds, this December in Key West will be quirky and cultural, as it should be.

1. Run A Triathlon

The Key West Triathlon 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.

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 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. 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!

4. 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.

5. Annual Holiday Bazaar

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

6. 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. More details located here

7. 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!

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