Christmas and the Holidays in Key West

As any regular visitor can tell you, Key West, aka the Conch Republic, is a truly unique and special destination any day of the year. You might think of us as a beach and watersports destination where you can swim, jet ski, and go snorkeling to your heartÂ’s content.

However, the Christmas holidays are when the magic really happens.

If you are staying at one of our premier vacation rental properties during this special holiday, you'll become aware of a sort of paradox going on in Key West. While our locals and visitors can most definitely go over the top with decorations, events, costumes, and so forth, the tempo is somehow less frantic than in other parts of America.

Maybe that's because we are a small, friendly Florida Keys town or maybe it’s the swaying palm trees and sunny weather — the December averages for Florida are a comfortable 77°F in the daytime and 70° at night.

LetÂ’s explore the most festive holiday events to experience during your magical Key West Christmas.

 

Key West Harbor Walk of Lights

Date and time: November 27th 2024 to January 1st 2025

Head down to the Key West Historic Seaport for the Key West Harbor Walk of Lights and the lighting of the Christmas tree. Expect to see more than 60,000 lights illuminating the harbor area in a spectacular light show that you wonÂ’t soon forget.

The Nutcracker Key West

Date and time: December 5th to 15th, various showtimes

With its tropical twist on Tchaikovsky's classic ballet, The Nutcracker Key West is a biennial extravaganza we always eagerly anticipate. The Tennessee Williams Theatre hosts this saga, which takes you through Old Town Key West, circa 1863, over the ocean, and under the waves to the reef.

The principal roles are performed by professionals brought in just for this production, and then the cast is rounded out with talented locals of all ages and skill sets as required. With a cast of 80, lavish sets and costumes, and remarkable production values, this is something you definitely won't want to miss.

 

Holiday Village & BeLighted Bike Ride

Date and time: December 6th at 5 pm

A (sort of) parade of a completely different stripe is the Holiday Village & BeLighted Bike Ride, a benefit for Wesley House Family Services. Staged at the Coffee Butler Amphitheater in the beautiful Truman Waterfront Park, this family-oriented gathering is full of holiday cheer and culminates in a lighted bicycle ride. Take this opportunity to see Key Westers apply their creativity and holiday spirit to their beloved bicycles, all while helping a worthy local organization.

 

Hometown Holiday Parade

In early December, the season kicks off with the Hometown Holiday Parade. Barely one month after the madness and excess of the Fantasy Fest parade, this small-town confection will warm your heart and put you in the mood for the month ahead. The floats have a very homemade feel, and most of the marching groups are not bands.

Expect to see a few pirates and "parrot heads" sprinkled into the mix, because, hey, it's Key West. But this is a family-friendly event. The kids are delighted to scramble for the candies being tossed their way and interact with the parade participants. No crushing crowds are lining the parade route, and there is room for everyone to spread out and enjoy the great holiday vibes as the procession moves down Truman Avenue and then up Duval Street to Eaton Street.

 

Conch Train Holiday Lights Tour

Date and time: December 9th, 10th and 13th to 23rd at regular times during the evening

If you just want to cruise around enjoying the holiday sights, walking or bicycling around Old Town in our glorious subtropical climate should be perfect for you. Another option is to take the Key West Holiday Lights Train Tour. This company sponsors the annual Key West Holiday Lights Contest so they will be sure to know where the very best displays are to be seen!

Tip: Old Town Trolley Tours are another great option for soaking up the festive atmosphere without the need to walk miles upon miles. Contact them to ask about the accessibility of the tours.

 

Eaton Street Christmas Stroll

Date and time: December 8th at 3:30 pm

One great way to start seeing the trimmings and get into the holiday mood is by joining in the
Eaton Street Christmas Stroll. This annual free event allows you to wander down historic Eaton Street while taking in the sights and meeting new friends. Stops at various venues along the route offer music, entertainment, snacks, and even a cocktail or two. DonÂ’t miss the Keys Choral Arts winter concert along the way for a dose of festive caroling and holiday music.

 

The Rudolph Red Nose 5K Run

Date and time: December 14th at 8 am

Feeling energetic? The annual Rudolph Red Nose 5K Run may be for you.  It's a serious race that doesn't take itself too seriously. And it benefits a worthy cause. Santa hats and reindeer antlers abound, and, of course, red noses. But the real kicker is everyone shows up in their finest Christmas pajamas!

This run benefits Positive Step of Monroe County, a 501(c)(3) non-profit organization serving Monroe County's highest-risk kids and their families, and runners and walkers of all ages and abilities are welcome to participate.

 

Schooner Wharf Lighted Boat Parade

Date and time: December 14th at 8 pm

Just a few days after the street parade comes the annual Christmas Schooner Wharf Lighted Boat Parade at the Key West Historic Seaport (previously known as Key West Bight). Fishing boats, sailing ships, yachts, catamarans, and dinghies cruise by, each festooned with Christmas lights and decorations ranging from the ridiculous to the sublime. Spectators line the harbor and fill up Schooner Wharf bars and restaurants to catch a glimpse of the light displays and a party ensues which lasts all evening and well into the wee hours.

Tip: The entire Key West Harbor Walk is decorated and lit up for the holidays, so while youÂ’re here for the light show you can enjoy a stroll to take in the sights and immerse yourself in the celebration.

 

Holiday Historic Inn Tour

Date and time: TBA, check the website for upcoming announcements

For a curated tour that is an evening's entertainment in itself, the Holiday Historic Inn Tour may be for you. Starting at the Key West Butterfly & Nature Conservatory on Duval St, the traveling party takes in the Conservatory and several historic Key West inns. Each is decked out in its holiday attire, and at each stop, your hosts will give you a tour of the property, and you will be offered holiday treats.

Tip: As you are checking out the various displays around the island, be sure to stop by Bayview Park to see the Official Christmas Tree and Menorah of the City of Key West. The tree is illuminated for the entire month, and there is a ceremonial lighting of the menorah on the first evening of Hanukkah.

 

Christmas Day on Duval Street

Date and time: December 25th all day

One of our favorite things to do on Christmas Day is to head for Duval Street to enjoy the all-day promenade of strolling visitors and locals in their finest (or wackiest) holiday attire. Many of the restaurants, bistros, and cafes along this main drag offer outdoor seating on decks, porches, or balconies overlooking the sidewalk parade out front, so this is a perfect way to enjoy brunch or dinner.

If you are a visitor to the island, we suggest you scout out your perfect spot earlier in the week and make a reservation to ensure you'll nab the best seats for your special day.

 

Sloppy JoeÂ’s Bar

Date and time: December 31st

Now it's time to cap off the Key West holiday season, wrap up one year, and welcome the next with the biggest event of all, New Year's Eve. Parties are hosted at restaurants and bars all over the island, many including dinner, cocktails, and live music.

Over on Lower Duval, at the historic Sloppy Joe's Bar, a giant conch shell descends at the stroke of twelve. Mounted on a pole on top of Sloppy's marquee, the shell looms over a throng of revelers filling the corner of Duval and Greene Street.

 

A Festive Winter Wonderland in Key West

And with that, another year is done, this fantastic holiday season wraps up, and a fresh New Year begins in Key West. Now you know what activities are on offer, all thatÂ’s left to do is to decide where to stay!