Christmas and the Holidays in Key West

Everything but the snow!

As any regular visitor can tell you, Key West is a truly unique and special destination any day of the year. But add in the sparkle and levity of the Christmas holidays, and then the magic really happens.

If you are staying at one of our premier Vacation Rental Properties during this enchanting season, 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 locales. Maybe that's because we are a small, friendly island town. Maybe it is the gorgeous December weather that makes us slow down and savor every moment. The December averages are 77°F in the daytime, and 70° at night. And of course, there is lots of sunshine!

Key West enjoys the same holiday traditions and customs as anyplace else- it's just that here, they often go in a distinctive Island direction. Santa may abandon the red velour and fur for a tropical print and shorts. In lieu of the sleigh, he may arrive in a dinghy pulled by eight dolphins. (Sorry, Rudolph.)  Live poinsettias and festooned palm trees stand in for the holly and spruce, although you'll often see those, too.

I love a 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 really 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 "parrotheads" 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. There are no crushing crowds 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 to Eaton Street.



Just a few days after the street parade comes the Schooner Wharf Lighted Boat Parade at the Key West Historic Seaport. Fishing boats, sailing ships, yachts and dinghies cruise by, each festooned with lights and decorations ranging from the ridiculous to the sublime. Spectators line the harbor and fill up the bars and restaurants along the parade route. A party ensues, lasting all evening and well into the wee hours.

The entire Harbor Walk is decorated and lit up for the holidays, so while you are here, you can enjoy a stroll to take in the sights and immerse yourself in the celebration.

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 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.

Of course, in Key West, we don't just decorate the floats and the boats. We will jump at any chance to dress up our houses, our cars and ourselves. And there is no better opportunity than the holiday season. With Christmas, Hanukkah, Kwanzaa and New Year's all converging within just a few weeks, we love to decorate everything in sight, and keep the party going all month long.

Deck the Halls

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.
Note: some of the links we provide here mention specific dates, and those are not necessarily the same every year. We know that many of our vacation rental guests return year after year, and often book a year in advance. So, we suggest that as your holiday vacation approaches, you consult this Key West Calendar of Events for each year's event dates.

If you just want to cruise around enjoying the decorations, 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 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!

For a curated tour that is an evening's entertainment in itself, the Holiday Historic Inn Tour may be for you. Starting off at the Key West Butterfly & Nature Conservatory on Duval, the travelling party takes in the Conservatory and three 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.



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.

Special Events

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 skillsets 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.

All the way at the other end of the entertainment scale, here is one for the grownups. The Key West Burlesque troupe offers up  The 12 Days of Stripmas, a jovial and highly entertaining folly in classic burlesque style at the Key West Theater on Eaton Street. A little risqué (of course,) but never crass or vulgar, Burlesque is an historic form of vaudeville entertainment which has enjoyed an immensely popular revival in recent years. And the Key West Burlesque company has kept it classic and classy for the past couple of decades. Their fresh, new Holiday edition promises you an excellent evening of polished, light-hearted entertainment.

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 A 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.

Christmas Day in Key West

After a month full of busy activity, the action cools down for the climactic big day. In a town that is always friendly and easygoing, the atmosphere seems even more cheerful, bright and embracing on Christmas Day. Of course Santa comes here as he does anywhere, so the morning is usually all about gift-giving with family and friends. But afterward, many locals love to head to their favorite beach. We are just entering the season when nearly every day offers up postcard-perfect weather. Clear, bright, sunny, and not too hot, a beach visit is definitely in order.

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. So 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 our 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.

Annnnd...The Grand Finale!

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. Ever since the first "ball-drop" in Times Square in 1907, people have been dropping all sorts of things at midnight on Dec. 31^st. Never happy to be outdone by anyone else, Key West offers up THREE midnight drops to choose from.

The Schooner Wharf Bar presents the Pirate Wench Drop, in which the costumed wench is lowered from the mast of a classic sailing ship docked at the Historic Seaport, right in front of the bar.

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 that 200 block of Duval.

And finally, perhaps our most famous drop, thanks to Anderson Cooper's frequent live coverage of the event, is The Drag Queen Shoe Drop at the Bourbon Street Pub. Since 1996, Sushi, the drag queen, perched in a giant red high-heeled pump, has been lowered at midnight from the gable of the pub to the 700 block of Duval Street below. Hundreds of partiers jam the Pink Triangle (as the intersection of Petronia and Duval is known) and shout the countdown to midnight.

And with that, another year is done, this fantastic holiday season wraps up, and a fresh New Year begins in Key West and everywhere.

Happy New Year, everyone!