15 Fantastic Ways to Celebrate the Holidays in the Florida Keys

The Florida Keys have their own lifestyle, so it’s only fitting that vacations in the Keys should be just as original. America’s southernmost city has dozens of ways to celebrate the season, but don’t forget the 125-mile island chain with celebrations along the way. From winter wonderland festivals to dazzling illuminated boat tours, there’s something for visitors and locals alike.

We’ve put together a list of 15 unique ways to celebrate the Florida Keys vacation.

1. Key West Holiday Festival

From illuminated parades on land and water to tours of the Holiday Historic Inn and New Year’s Eve parties, Key West Holiday Fest hosts festive celebrations for the whole family. Until December 31, Key West transforms into an island full of vacation fun. Consult the calendar for the complete program.

2. Wesley House Family Services Holiday Village and BeLighted Bike Ride

The second annual BeLighted Holiday Village and Bike Ride will take place on December 2 in Key West. There will be food trucks, crafts for children, a contest for the best bike and photos with Santa Claus. The BeLighted Bike Ride is a parade of bikes down Duval Street, all decked out in Christmas lights and decorations.

3. Florida Keys Holiday Festival

It may not snow in the Keys, but there will be a 30-ton snow hill during the 18th Florida Keys Holiday Fest in Islamorada. On December 2, snow will also fall during the lighting of the 35-foot-tall tree! The festival also includes a holiday parade, Santa’s Sweet Shoppe with gourmet desserts and coffee, a holiday bazaar, a gingerbread house contest, and more.

4. Headlight illumination

A truly unique Keys holiday tradition, 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 entertainment and a visit from Santa Claus.

5. Key West City Hometown Holiday Parade

Santa Claus will make an appearance at the Key West City Hometown Holiday Parade on December 3. This very popular parade includes local marching bands, school groups and floats. It starts at White Street and Truman Avenue in Bayview Park.

6. Eaton Street Christmas Walk

This free December 4 family event takes you on a stroll through theaters, cultural sites and churches to get you into the holiday spirit! Start at St Paul’s Episcopal Church in Key West, for a short program of secular and religious music for the season, then work your way through stops that include a short Christmas film, live music, cocktails and a Art Gallery.

seven. Nutcracker Key West

The Nutcracker Key West is a Keys-themed adaptation of this classic holiday ballet. This show features 60 children and adults from the Florida Keys and 15 professional dancers from around the world. This representation is a historical recreation and includes prawns, jewels of the Atocha, and the famous local roosters roaming free. There are six performances from December 7 to 11.

8. Zonta Tree Festival

Stroll through dozens of decorated trees during the 12th Annual Tree Festival from December 7-10. The Zonta Marathon Club organizes the event every year. Trees are decorated and donated by locals, businesses and clubs. The event is free. You can buy a raffle ticket for the chance to take home your favorite tree.

9. Holiday sites and festive night tours of the Old Town

The Old Town Trolleys are a classic way to see Key West. For the holidays, the popular green and orange cars are decorated with Christmas lights and take you to the best decorated neighborhoods on the island. See how the island transforms for the holidays with a guided tour departing from the famous Mallory Square.

10. Illuminated boat parades

You can’t get more Florida Keys than a parade of illuminated boats! Stock Island, Key West, Key Largo and Key Colony Beach will all host festive traditions on the water this holiday season. Take a seat along the shore to watch boats covered in holiday lights and decorations cruise the Keys on December 9, 10 and 11.

11. Visits to Historic Holiday Inns

Take a tour of Key West’s historic inns. The island is home to dozens of hostels, and this is an opportunity to see some of them decked out in their finery. These self-guided tours let you experience unique architecture, history, and vacation 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 drink, and a visit from Santa on December 9th.

13. Rudolph Red Nose 5k

Put on your holiday pajamas and get ready to run! The southernmost holiday race in the country takes off on December 17. The most festive and unusual pajamas receive a prize!

14. Crane Point Winter Wonderland

Bring the family to enjoy this winter wonderland in paradise. There will be a chocolate fountain, reindeer, Santa Claus and more. The forecast calls for snow during this annual festival, so be prepared on December 17.

15. New Year’s Drops

Key West has its own New Year’s traditions! Ring in 2023 with the conch drop at the famous Sloppy Joe’s Bar on Duval Street. Celebrate the 25th anniversary of the huge drop in red high-heeled shoes (wearing drag queen sushi) at the Bourbon St. Pub/New Orleans Housecomplex. Schooner Wharf Bar will have a pirate girl descend from the mast of the tall ship at midnight. A huge replica of a lime wedge will splash in a life-size margarita glass at the Ocean Key Resort & Spa, and there’s a drop of tuna at the Smokin’ Tuna Saloon.

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