5 Awesome Itineraries for Celebrating the Holidays in Orlando

holidays in orlando

With temperatures still hovering in the 70s, it’s no surprise Orlandoans may have a bit of trouble getting into the holiday spirit. Luckily, Central Florida knows how to celebrate — and decorate — with a slue of Christmas events and holiday displays taking place all around the city. If you need a little help finding your holiday cheer, these last minute holiday staycation itineraries are just what the doctor (or Santa) ordered.

Downtown/Lake Eola

Lake Eola Park is decked out for the season with festive lights, holiday decorations, and a beautiful six-story tall Christmas tree, making it the perfect destination for your weekend staycation.

Stay: EO Inn, Thornton Park, from $159/night

Play: You can admire the Christmas tree in the park nightly, but make sure to catch the synchronized light show, which happens every hour beginning at 5:45pm. Other holiday events include Holiday Movies at Lake Eola Park at 7:00 pm on December 15th (National Lampoon’s Christmas Vacation), 17th (Elf), and 22nd (The Nightmare Before Christmas), and a performance of The Nutcracker by Russian Ballet Orlando on December 16th at 7:00 pm. A full listing of events is available online.

holidays in orlando

Dine: Take your pick of any of Thornton Park’s beloved restaurants, including Dexter’s, Soco, and The Stubborn Mule. Rise early for breakfast at Benjamin French Bakery & Café.

Drink: Just a short walk from Lake Eola, Frosty’s Christmastime Lounge is a Christmas lover’s paradise where the holidays never end and alcohol-infused snow cones are on the menu. Next, continue your Christmas bar crawl with a stop at The Courtesy, which has been transformed into Miracle on Orange through December 24 featuring seasonal cocktails and a festive atmosphere.

frostys-christmastimelounge holidays in orlando
Frosty’s Christmastime Lounge


The master-planned community of Celebration was developed by Disney, and during the holidays there’s no place you’ll be happier. The central town area, known as Celebration Town Center, is abuzz with a steady stream of holiday events sure to ignite your holiday spirit.

Stay: The Bohemian Hotel Celebration, from $136/night in December

Play: During the holiday season, Celebration is best known for its nightly snowfall on Market Street. Snowfall occurs every hour on the hour, beginning at 5pm and ending at 9pm. Horse-drawn carriage rides are also available, and you’ll definitely want to snap a selfie in front of the Christmas tree on Front St. Afterwards, wander the quiet neighborhood streets to take in the dazzling lights.

Celebration Town Center

Dine: For a romantic night out, head to Columbia Restaurant for authentic Spanish and Cuban fare, or dine on-site at the Bohemian for dinner at Lakeside Bar + Grill (there’s live jazz on Saturday evenings). A five-minute drive outside of Celebration Town Center will land you at Holler & Dash, a new Southern biscuit house restaurant open for breakfast and lunch. For dessert, treat yourself to a scoop (or 3) of Kilwin’s peppermint ice cream, or wander over to Wonderland Cookie Dough for a cup of edible cookie dough.

Drink: Celebration’s small size contributes to its walkability, and drink options are steps away from one another. Start with a glass of wine at Imperium, then walk around the corner to local favorite Celebration Town Tavern for cocktails and a selection of 99 beer varieties.

Winter Park

Wondering where you can ice skate, marvel at holiday decorations, complete your last minute gift shopping, and dine at some of Central Florida’s best restaurants? Look no further than Winter Park, a walkable district that’s just far enough from home to feel like a getaway.

Stay: The Alfond Inn from $189/night for Florida residents

Play: For totally free fun, take a walk through Central Park to admire the holiday decorations and Christmas trees. In Central Park you’ll also find an ice-skating rink, Winter in the Park. $13 gets you skates and all day admission. Park Ave. is perfect for your holiday shopping needs, with a variety of boutiques and specialty shops dotting the brick lined streets.

holidays in orlando

Dine: Prato and Luma on Park, both located in the heart of Park Ave., are some of the area’s best restaurants for a night out. Budget eats are available at Shake Shack (watch the sunset in their outdoor seating area) and Barnie’s Coffee Kitchen. Satisfy your sweet tooth at KrungThep Tea Time with a towering brick toast dessert, or munch on chocolate covered popcorn from Peterbrooke Chocolatier.

Drink: Sip on wine and craft beer at The Parkview on Park Ave., or hop in the car to check out the fast-developing area of N. Orange Ave. in the old State Auto Body building. Sip craft coffee at Foxtail Coffee, and then treat yourself to craft beer at The Bear & Peacock brewstillery around the corner.


The University of Central Florida (UCF) campus is a flurry of Christmas activity, with the CFE Arena serving as the epicenter of holiday happenings all month long.

Stay: UCF makes a great evening or day trip, but if you prefer to stay overnight choose from one of the numerous nearby hotels ranging from $125 to $174/night.

Play: Light Up UCF at the CFE Arena includes daily events such as ice-skating, holiday movies, visits with Santa, and so much more. The ice-skating rink is Orlando’s largest and is open daily at 5pm Monday-Friday, and 12pm Saturday and Sunday. The Holiday Film Festival is another big draw, featuring holiday movie screenings every Friday and Saturday at 7pm and 9:30pm. 


Dine: You’re in college town, so get your foodie fix at one of many fast-casual style establishments along University Blvd. Indulge in a slice of pizza as big as your head at Lazy Moon, get your fill of carbs at Spoleto, a local Italian chain restaurant, and grab a treat from Insomnia Cookies.

Drink: You can sip a glass of your favorite Christmas ale at World of Beer, which has over 500 beers available.

St. Augustine

If you’re itching for a weekend getaway, hop in the car and make the trip to St. Augustine to kick off the New Year. Explore the historic city by day, while taking in thousands of magical holiday lights at night.

Stay: The Bayfront Marin House or The Old Powder House Inn, from $209/night

Play: Nights of Lights is an annual holiday event where the historic city comes alive with splendid lights and holiday activities. Visit in January to draw out the holiday season, as the lights display continues through January 31, 2018.


Dine: Dine at the Ice Plant for craft cocktails and exceptional food in an atmosphere reminiscent of the 1920s. An alternative option is to taste the city during a horse and carriage food and wine tour of the city (Saturdays only) with The Tasting Tours.

Image credit: Ice Plant Bar
Image credit: Ice Plant Bar

Drink: The St. Augustine Distillery offers free tours daily (which includes free samples of their spirits!) and the Ice Plant, located in the same building, serves up delightful craft cocktails. For something to warm you up, make your way to Claude’s Chocolate for a steaming cup of hot cocoa.

Continue the Festivities…


All images by Stephanie Patterson except for:

Florida food and travel photographer and writer Stephanie Patterson

About the Author/Photographer:
Stephanie Patterson is the managing editor of Orlando Date Night Guide. She’s a talented professional food and travel photographer and writer with a passion for creativity, the beach and great eats. When she’s not taking photos or writing, you can find her exploring the state for her Florida travel blog, Travel Taste Click. Find her online at www.spattersonphotography.com and www.traveltasteclick.com.


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