The Florida Keys has its own unique lifestyle, so it’s only fitting that the holidays in the Keys are just as original. America’s southernmost city has dozens of ways to celebrate the season, but don’t forget about the 125-mile island chain with celebrations along the way. From winter wonderland festivals to dazzling lighted boat tours, there is something for visitors and locals alike.
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We put together a list of 15 unique ways to celebrate the holidays in the Florida Keys.
1. Key West Holiday Fest
From lighted parades on land and the water to Holiday Historic Inn Tours and New Year’s Eve parties, Key West Holiday Fest has festive celebrations for the whole family. Until December 31, Key West turns into an island full of holiday fun. Check the calendar for the full lineup.
2. Wesley House Family Services Holiday Village And BeLighted Bike Ride
The second annual Holiday Village and BeLighted Bike Ride is on December 2 in Key West. There will be food trucks, crafts for the kids, a best bike contest, and photos with Santa. The BeLighted Bike Ride is a parade of bikes up Duval Street all decked out with holiday lights and decorations.
3. Florida Keys Holiday Fest
It may not snow in the Keys, but there will be a 30-ton snow hill at the 18th annual Florida Keys Holiday Fest in Islamorada. On December 2, snow will also fall during the lighting of the 35-foot-tall tree! The fest also includes a holiday parade, Santa’s Sweet Shoppe with gourmet desserts and coffee, a holiday bazaar, a gingerbread house contest, and more.
4. Lighting Of The Lighthouse
A truly unique Keys tradition for the holidays, the annual lighting of the iconic Middle Keys lighthouse takes place on December 3 in Marathon. Hosted by the Faro Blanco Resort & Yacht Club, families can enjoy food, music, live performances, and a visit from Santa.
5. Key West City Hometown Holiday Parade
Santa will make an appearance at the Key West City Hometown Holiday Parade on December 3. This wildly popular parade features local marching bands, school groups, and floats. It kicks off at Bayview Park’s White Street and Truman Avenue.
6. Eaton Street Christmas Stroll
This free family-friendly event on December 4 takes you on a stroll through theaters, cultural landmarks, and churches to get you in the holiday spirit! Begin at St Paul’s Episcopal Church in Key West, for a short program of secular and religious music for the season, then make your way through stops that include a Christmas short film, live music, cocktails, and an art gallery.
7. Nutcracker Key West
The Nutcracker Key West is a Keys-themed adaptation of this classic holiday ballet. This performance includes 60 Florida Keys children and adults and 15 professional dancers from around the world. This performance is a historical recreation and includes shrimp, jewels of the Atocha, and the famous free-roaming local roosters. There are six performances from December 7 through the 11.
8. Zonta’s Festival Of Trees
Take a walk through dozens of decorated trees at the 12th annual Festival of Trees from December 7 through 10. The Zonta Club of Marathon puts on the event each year. The trees are decorated and donated by locals, businesses, and clubs. The event is free. You can buy a raffle ticket for a chance to take home your favorite tree.
9. Old Town Trolley’s Holiday Sights & Festive Night Tours
The Old Town Trolleys are a classic way to see Key West. For the holidays, the popular green and orange cars are decorated with holiday lights and take you through the best-decorated neighborhoods on the island. See how the island transforms for the holidays with a guided tour leaving from famous Mallory Square.
10. Lighted Boat Parades
You can’t get more Florida Keys than a lighted boat parade! Stock Island, Key West, Key Largo, and Key Colony Beach will all host the festive traditions on the water this holiday season. Grab a seat along the shore to watch boats covered in holiday lights and decorations cruise the Keys on December 9, 10, and 11.
11. Holiday Historic Inn Tours
Take a tour of the historic inns of Key West. The island is home to dozens of inns, and this is a chance to see some of them decorated in their holiday best. These self-guided tours give you a chance to experience the unique architecture, history, and holiday decor. Tickets are available for December 9 and 16.
12. Key West Art & Historical Society Holiday Bazaar
The sixth annual concert and holiday shopping event lets you enjoy the porch and walkway of the historic Key West Museum of Art and History. Enjoy a holiday light show, unique crafts from local artisans, holiday music, food and drinks, and a visit from Santa on December 9.
13. Rudolph Red Nose 5k
Put on your holiday pajamas and get ready to run! The southernmost holiday run in the country takes off on December 17. The most festive and unusual PJs get a prize!
14. Winter Wonderland At Crane Point
Bring the family to enjoy this winter wonderland in paradise. There will be a chocolate fountain, reindeer, Santa Claus, and more. The forecast is calling for snow at this annual festival, so come ready on December 17.
15. New Year’s Eve Drops
Key West has its own New Year’s Eve traditions! Ring in 2023 with the conch shell drop at the famous Sloppy Joe’s Bar on Duval Street. Celebrate the 25th anniversary of the huge, the red high-heel shoe (carrying drag queen Sushi) drop at Bourbon St. Pub/New Orleans Housecomplex. Schooner Wharf Bar will lower a pirate wench from the tall ship’s mast at midnight. A huge replica of a Key lime wedge will splash into a life-size margarita glass at Ocean Key Resort & Spa, and there’s a tuna drop at the Smokin’ Tuna Saloon.
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