24 Days of Holly Jolly Joy

24 Days of Holly Jolly Joy to Celebrate the Holidays in Orlando

It’s the most wonderful time of the year! Celebrate the holidays in Orlando with our list of joyful activities to partake in together every single day from December 1 – 24.

December 1: Insta-worthy photos with Santa

Feel like kids again and get epic shots with Santa this year at Wall Crawl. The indoor selfie paradise has transformed more than half of its walls into holiday-themed sets perfect for Insta-worthy (and Christmas card-ready) photos with your boo. Book a time slot for December 1 when Santa comes to town. Free photos with Santa are included with your $25 entry ticket, and you’re welcome to snap your own photos in the space with your phone and camera. FYI: photos with Santa are also available on December 22.

photos with Santa at Wall Crawl
Image credit: Wall Crawl

December 2: Epcot Candlelight Processional

For some Orlandoans, Epcot’s Candlelight Processional is the holiday event of the season. Each night, a celebrity narrator tells the story of Christmas with the help of a choir and orchestra, and it’s pretty darn magical. Neil Patrick Harris will be narrating December 2 – 5. We attended during a hosted visit last year and put together this post with our tips for experiencing this holiday bucket list item. While the exact details have changed for 2019, the advice still holds up for planning your visit this year. 

Epcot Candelight Processional

December 3: Make a DIY Wreath

Deck your walls with a special DIY project: a custom holiday wreath! Head to Lakehouse in Lake Nona to make your very own holiday hoop wreath under the guidance of the pros from Buds Flower Co. You can even upgrade your ticket to include wine for an extra $5. Or, make your way to The Grape & The Grain for Enlighten Us’ grapevine wreath workshop with instructor Tracy Post of Petals & Stems Market, a mobile fresh flower market. You can sip on a complimentary frozen sangria while you work. We hear it helps to get those creative juices flowing and unearth the muse.

If December 3 doesn’t work for you, check out our roundup of December workshops. There are over a dozen holiday-themed classes to choose from including wreaths, ornaments and cocktails. 

Image credit: Enlighten Us

December 4: Play in the Snow

We don’t get real snow in Central Florida, but that doesn’t mean we can’t pretend. Play in the flurries (ok, they’re actually soap flurries) nightly in Celebration at 6, 7, 8 and 9pm from November 30 – December 31. Or, frolic in the real deal at Wekiva Island’s Winter Wonderland, which has a host of holiday happenings including snow flurries and a real snow slide. Lake Nona will also have occasional snowfall during their Oh What Fun Holiday Festival. RDV Ice Den is also bringing real snow to Central Florida for Snow Fest, taking place later in the month on December 14.

Snow at Wekiva Island
Image credit: Wekiva Island

December 5: 41st Annual Christmas in the Park

While you normally have to go inside of the Morse Museum to view its impressive collection of Louis Comfort Tiffany glass, the annual Christmas in the Park is a chance to see a bit of the collection outdoors for free, accompanied by a holiday concert to boot! Nine stained glass windows will be llluminated as the Bach Festival Choir and Brass Ensemble perform a free concert in Winter Park’s Central Park. The windows will remain lit for about 30 minutes after the concert concludes.

FYI: you can bring an adult beverage to enjoy. And a tip: trying taking the SunRail as parking can be a bit maddening.

Image courtesy of the Charles Hosmer Morse Museum of American Art, Winter Park, Florida

December 6: Outdoor Holiday Movie Night

Cozy up underneath the stars to watch a holiday classic and welcome the weekend. While there are dozens of holiday movie screenings happening in December, our personal favorite for date night is Leu Gardens’ monthly movie night. On December 6, watch the Christmas classic National Lampoon’s Christmas Vacation. You’re allowed to bring in outside food and beverage (that includes beer and wine) to enjoy during the flick. Or grab something from the on-site food vendors. Our recommendation: provisions from East End Market with some yummy mulled wine in a thermos!

Also on December 6, Enzian Theater will be screening Elf in Winter Park’s Central Park as part of the theater’s monthly Popcorn Flicks in the Park outdoor movie series. Get the details here.

Orlando Events for September 2018
Leu Gardens movie night | Image credit: Leu Gardens

December 7: Gingerbread & Craft Beer Pairing

Now in its 3rd year, Playalinda Brewing Company’s (Hardware Store location) Gingerbread & Craft Beer Pairing takes Christmas cookie consumption to a whole new level. The special pairing will be available while supplies last on December 7 and includes a flight of homemade cookies with special icings paired expertly with Playalinda brews.

Image credit: Playalinda Brewing Co

December 8: Holiday Pops Concert

Take advantage of the beautiful weather and unwind before beginning another workweek at the Orlando Philharmonic’s annual Sounds of the Season Holiday Pops concert. Central Park in Winter Park is a hub for holiday activity, especially concerts such as this one. Did we mention it’s totally free? Bring a lawn chair and some blankets to get in the spirit with holiday tunes.

Orlando Philharmonic holiday pops concert in Winter Park, FL
Image credit: Orlando Philharmonic

December 9: Christmas Bar Hop

During the holidays, some of our favorite bars are reimagined as holiday pop ups and decked to the nines in festive decor. This year, The Courtesy has again become Miracle on Orange, as part of worldwide holiday pop-up concept with an exclusive holiday drink menu. Cocktails are served in festive glassware including a pretty epic new concoction served in a T-Rex mug. The Miracle holiday pop-up bar concept has also expanded to Daytona Beach this year at Hard Rock Hotel Daytona Beach, where the hotel’s Sessions Bar will reopen with retro-themed holiday digs from November 29 – December 30. You can browse all of the Miracle bars in Florida here.

Other holiday pop ups include the tiki-themed Sippin’ Santa at Avanti Palms Resort and Jock Lindsey’s Hangar Bar at Disney Springs, which has become Jock Lindsey’s Holiday Bar for the season. And for year-round Christmas fun, there’s always our beloved Frosty’s Christmastime Lounge.

Image credit: Miracle on Orange

December 10: Girl’s Club Holiday Edition

Shameless plug: Our crazy popular Girl’s Club event series presented by Jane is back on December 10 and this month is a special holiday edition in downtown Orlando! The details are a secret until two days before the event when we’ll send you all the juicy details. We won’t be serving food at this event, but we’re starting later (7:30pm) to give you the time to dine at one of the dozens of restaurants nearby AND we’re keeping costs down with this one, since we know the holidays are such a wallet suck. We’ve only got a few tickets left–you can get yours here.

December 11: A Christmas Carol – A Ghost Story of Christmas

There are a few holiday productions you just can’t miss, and A Christmas Carol is one of them. See it at Winter Garden’s historic Garden Theatre select dates November 29 – December 22 where the show’s ghostly aspects take center stage in this adapted production. Stick around Winter Garden after the show to explore the holiday decorations on foot. 

A Christmas Carol at Garden Theatre
Image credit: Garden Theatre (photo by Patrick R. Murphy)

December 12: Gingerbread House + Champagne

December 12 is National Gingerbread House Day, didn’t you know? Go big by creating your own gingerbread house while sipping on champagne at The Ritz-Carlton Orlando, Grande Lakes. The resort is hosting Bubbles & Ginger, an adults-only gingerbread house workshop where you’ll also get to nibble on a special menu of treats like cheese and charcuterie, mini beef wellingtons, jumbo crab cakes and more. The cost to participate is $255 per group of up to 4 people. Call 407-393-4648 to reserve. 

Image credit: Ritz-Carlton Orlando, Grande Lakes

December 13: Friday the 13th Christmas Party

What do you get when you mix Friday the 13th with ugly sweater season? World of Beer Downtown Orlando’s Friday the 13th Christmas Party! Highlights include an ugly sweater contest (judged by Dirty Santa), $5 Christmas drinks (we like the sound of the Mistletoe Margarita) and an extended happy hour.

Lake Eola Date Night ideas
World of Beer Downtown Orlando

December 14: Skydiving Santas at Cocoa Beach

Cocoa Beach takes the cake for most unique holiday celebration with its Skydiving Santas of Cocoa Beach event on December 14. It’s worth the drive over early in the morning to line up around the Westgate Cocoa Beach Pier and watch dozens of Santa skydivers descend onto the beach from above. 

Skydiving Santas at Cocoa Beach Pier
Image courtesy of Westgate Cocoa Beach Pier | Image by Billy Ocker

December 15: Christmas Cookie Run

Is your personal motto something along the lines of “will exercise for food?” Join the Christmas Cookie Run, a 5K fun run with Christmas cookies as your prize. Other race activities include photos with Santa, a costume contest and snow.

Image credit: Christmas Cookie Run

December 16: Holiday Drink Pub Crawl in Sanford

Multiple bars in Sanford have crafted specialty drinks for the holiday season. While the official pub crawl is taking place on December 3 to help kick off the Holiday Tour of Homes, the drinks will be available all month long. Here’s a list of participating locations and drinks:

  • Luisa’s Cellar: “Gluwein” or “Coquito”
  • The Old Jailhouse Sanford: “Bohemian Stocking” made with the national spirit of the Czech Republic, Becherovka
  • Hollerbach’s Willow Tree Café: “Mozart Mint Martini” white chocolate liqueur, whipped vodka and icemint schnapps
  • The Imperial at Washburn Imports-Sanford: “Blood Orange Manhattan” 
  • Deviant Wolfe Brewing: “Exterior Illumination” is a German Bock that is malty and toasty like a warm fire
  • Tuffy’s Bottle Shop & Lounge: “The BIG Apple” featuring Absolute Apple Vodka, St. Elizabeth’s Allspice Dram, and more
Bohemian Stocking from The Old Jailhouse | Image credit: @drinksanford

December 17: Christmas at Gaylord Palms

It wouldn’t be Christmas in Orlando without a visit to Gaylord Palms. Some of our favorite aspects of the resort’s Christmas celebrations are ICE! featuring The Polar Express, the #LIT Light Show, Cirque Dreams Unwrapped Stage Show, Christmas Tree Trail and the ice slide and snow tubing. It’s totally worth a visit whether you do it as a day trip or a mini holiday staycation. Partake in the festivities now through January 5, 2020.

Ice slide at ICE! during Christmas at Gaylord Palms. Image credit: Kristen Manieri

December 18: Miss Bennett: Christmas at Pemberley

Treat your favorite bibliophile with tickets to see Miss Bennet: Christmas at Pemberley at Orlando Shakes. This performance is a sequel to Jane Austen’s Pride and Prejudice, and is a romantic comedy telling the story of middle sister Mary Bennet. Catch the show select dates from December 4 – 29. Hot tip: if you’re under 35, tickets to evening performances and weekend matinees December 18 – 22 are just $25 for you (use code 25UNDER35).

Miss Bennett: Christmas at Pemberley | Image credit: Orlando Shakes, photo by Christian Knightly

December 19: Dinner and a Spooky Holiday Show

Get a taste of the darker side of Christmas this year. Victorian horror troupe Phantasmagoria will perform their newest holiday show, “Through a Christmas Darkly,” at Maxine’s on Shine on December 19. This one of a kind dinner show is sure to be a feast for the senses with delicious cuisine (your ticket includes two courses plus beer or wine) paired with spooky Christmas stories and legends. 

Image credit: Phantasmagoria

December 20: Free Carriage Ride in Downtown Orlando

The Church Street District is celebrating all month long with 30 days of Christmas in Downtown Orlando. There will be festive decor, light shows, music, and even snow! But we recommend visiting on a Thursday or Friday night to take advantage of live entertainment and FREE horse drawn carriage rides between 6-10pm. Stop by the iconic Lake Eola Christmas tree while you’re in the area, it’s an easy 15-minute walk away.

Image credit: Church Street District

December 21: Ugly Sweater Celebrations

Take your favorite ugly sweater out of storage and rock it at one of three celebrations happening on December 21. First up is Reunion Resort’s Ugly Sweater 5K. Put some thought into your ugly sweater attire because there will be a contest with prizes awarded for the ugliest sweater and best group concept. All race participants will receive a medal plus access to a pancake bar after the run. 

If drinking in your ugly sweater sounds more appealing than running in it, check out Boxi Park’s Ugly Sweater Holiday Party (you get a free welcome drink for dressing up) or join the Ugly Sweater Pub Crawl in downtown Orlando (there are 7 stops, so please use Uber, Lyft, or have a designated driver).

Image credit: Boxi Park Lake Nona

December 22: Go Ice Skating Outside

You can go ice skating on a real ice rink at RDV Ice Den (year round), The Ice Factory of Central Florida (year round), and at Light Up UCF (through January 5, 2020). But Lake Nona takes the cake this year with an outdoor ice skating rink that’s sure to up your levels of holiday cheer. Rentals begin at $10 and the rink is open Thursday from 4-10pm, Friday-Saturday from 11am-10pm and Sundays from 11am-9pm, November 29, 2019 – January 5, 2020.

Image credit: Lake Nona

December 23: The Nutcracker

The Nutcracker is an absolute must-see during the Christmas season. Orlando Ballet will be performing this Christmas classic at Dr. Phillips Center December 13 – 15 and again from December 20 – 23. Don’t miss this much-loved holiday tradition.

Image credit: Orlando Ballet

December 24: Holiday Lights

Before tucking in to bed on Christmas Eve, head out for a leisurely drive–or walk–through some of Central Florida’s best holiday light displays. Places like Mount Dora, Winter Park, Celebration (don’t skip the lights on Jeater Bend!) and Winter Garden all have dizzying amounts of twinkling lights that will make you ooh and ahh. You can find a list of our favorite spots for holiday lights here.

Image credit: Johanessen Lights

Feature image credit: Lake Nona

Disclosure: Some of the events mentioned in this post are hosted by our valued advertising partners.


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