For the 50+ Traveler
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It’s rare for Pensacola to have snow for Christmas, but the brilliant snow-white Gulf beaches are the next best thing, and what the city lacks in snow, they more than make up for with a generous helping of holiday cheer. From award-winning Christmas light displays to holidays at the zoo to Santa Claus parachuting in, the City of Five Flags really knows how to do the holiday up right.

Here are 11 of the best experiences you should check out in Pensacola this Christmas. Unless otherwise noted, these events are still scheduled to take place this year. For those that have been canceled due to COVID-19, the city tells us that they are already making plans for next year. In any event, you should contact the organizers or visit their websites to get updates just to be sure before heading out.

The Christmas tree at Winterfest in Pensacola, Florida.

1. Winterfest

Winterfest is a season-long holiday celebration in downtown Pensacola featuring an eclectic array of events and music. It all begins on Black Friday following the annual Elf Parade as the mayor throws the switch on over 400,000 lights that light up the historic buildings, shops, and the city’s Christmas tree.

Along the streets there are live street performers, pop-up concerts, carolers, restaurants, and plenty of shops that you can duck into to check off a few items from your Christmas gift list.

You can either walk, catch a ride on a pedi-cab, or take a horse-drawn carriage ride down the city streets. A highlight of Winterfest is the tram tour, a 60-minute ride through the gorgeous holiday lights complete with singing carolers acting as your guides. The tram takes you to Historic Pensacola Village, where you’ll hear live jug bands, go on a scavenger hunt, eat hot and spicy gumbo, and hear Papa Noel retell the story of the Cajun Night Before Christmas.

Admission is charged for certain events. Check their event calendar for pricing and visit the Winterfest website for the event schedule.

Pro Tip: There is free street parking, but spaces are limited and it gets really crowded. You best bet is to check the official Pensacola Parking website to locate paid and secure parking.

The Elf Parade in Pensacola, Florida.

2. Pensacola Elf Parade

The Pensacola Elf Parade is one rockin’ good time -- literally -- with bands, carolers, even an appearance by Elvis!

The parade takes place each year on Black Friday beginning around 4:00 p.m. There are plenty of chances to win prizes in one of the many contests like the Best Costume Contest, Best Decorated Stroller and Wagon Contest, and how could anyone pass up entering the Ugly Sweater Contest? Grab a cup of warm cocoa and snacks at the Gingerbread House before the celebration ends with a bang -- a glorious holiday fireworks show.

Important Note: Unfortunately, due to COVID-19, the Elf Parade has been canceled for 2020, but the city promises it will be back next year.

3. First City Lights

Each year, a dazzling display of lights line the streets of downtown Pensacola from Palafox to Plaza de Luna beginning Black Friday and running through New Year’s Eve. It’s called First City Lights. Stoll the streets of the historic city, do a little Christmas shopping in the many shops, and enjoy exceptional dining along the way.

Sowell’s North Pole Christmas Lights Display in Florida.

4. Sowell’s North Pole Christmas Lights Display

For well over 15 years, Michelle Sowell and her family have opened their farm and their hearts to the public, sharing the spirit of Christmas through an incredible light show. Sorry, that is an understatement. You have to see it to believe it. Walk, drive your car, or ride a train through a display featuring over 1 million holiday lights and dozens of beautiful handmade displays all while listening to Christmas Radio. There are even camels and zebras roaming the farm. Really! The display has so much holiday spirit that it won first place and $50,000 on ABC’s The Great Christmas Light Fight.

The light show is open from December 1 to Christmas Day from dusk to 9 p.m. The cost of admission allows you to drive through as many times as you like for the evening. Train rides are free for children under 1.

Pro Tip: Weekends are the busiest times for the farm, so it’s best to visit on weeknights.

5. Lighted Boat Parade

From dinghies to yachts, they all light up with holiday cheer during the Pensacola Lighted Boat Parade. The boats line up at Sabine Marina at 5 p.m. then loop around Little Sabine Bay and end at Quietwater Beach Boardwalk.

Pro Tip: The best vantage point to see the boats is where they come into the boardwalk, where the kids will be greeted by Santa and everyone will thrill to a spectacular fireworks display.

6. Christmas ZOObilee

The Gulf Breeze Zoo is located just across Escambia Bay from Pensacola and is a fun ramble through the animal exhibits, but when Christmas rolls around, the zoo becomes magical during the annual Christmas ZOObilee celebration. Every Saturday and Sunday from mid-December to Christmas, the zoo features holiday concerts, character artists, Sounds of the Season concerts, and every Sunday, visits with Santa. And you can put your Christmas building skills to the test to win prizes during the annual Gingerbread House Contest.

The zoo is open from 9 a.m. to 4 p.m. (last admission is 3 p.m.). Visit the Gulf Breeze Zoo online for current admission prices.

7. A Lionel Christmas

What would Christmas be without toy trains? The West Florida Railway Museum hosts this nostalgic event every Friday and Saturday at 3 p.m. throughout December at their museum railway depot that’s over 100-years old. Visitors will get to watch the trains clickity-clacking through meticulously handcrafted landscapes amid holiday lights and steaming cups of hot chocolate. Admission is free, but donations are requested.

Pro Tip: Museum hours and days of operation may be affected by COVID-19. Please email the museum at [email protected] to verify their schedule.

The Pensacola Children’s Choir's Christmas on the Coast.

8. Christmas On The Coast

The historic Saenger Theater rings out with the glorious sounds of Christmas as the Pensacola Children’s Chorus presents Christmas on the Coast. The warm southern winter is magically transformed into a winter wonderland as the choir sings your holiday favorites during the show that has been recognized as one of the best annual events in the city.

There are three performances: December 11 and 12 at 7:30 p.m., and Sunday, December 13, at 2:30 p.m. Contact the Saenger at (850) 595-3880 for ticket information.

Pro Tip: Seating will be limited this year due to COVID-19. Get your tickets early.

9. Santa Drop

Look! Up in the sky! It’s Santa Claus! And he’s dropping in at the iconic Flora-Bama on the snowy white Gulf beaches. Seriously, each year, the jolly old man parachutes down to the historic eatery that straddles the Alabama-Florida state line and then lets children of all ages sit on his lap to tell him what they want for Christmas.

This year’s event will be held December 12 from 11 a.m. to 2 p.m. with lots of live music, face painting and games for kids, and their world-famous Bushwhackers for mom and dad.

Editor's Note: If you're in the area and want to hop states, check out Gulf Shores, Alabama.

The Holiday Cube at Plaza Ferdinand in Pensacola.

10. Holiday Cube

Need a pic for your Christmas cards? Stop by Plaza Ferdinand and take your photo in front of the Holiday Cube. The city invites you to visit the cube and take your photo in front of any of the four beautiful holiday and Gulf Coast-themed images and sing along with the singing Christmas tree that will really get you into the holiday spirit.

Pro Tip: While you’re visiting downtown Pensacola taking that selfie at the Holiday Cube and dancing to the music, visit the other themed Christmas trees within a block of the cube -- the Grinch Tree at the corner of Tarragona and Intendencia, the Southtown Tree on Intendencia, and the Winterfest Tree at Palafox and Government. It’s all free.

11. O’Riley’s Annual Santa Pub Crawl

Time to get into the holiday spirit, or spirits, actually, at the annual O’Riley’s SantaCon. This is a good old-fashioned pub crawl sponsored by O’Riley’s Irish Pub where you can have a quick pint of some of the best brews in the city. But this crawl has a purpose -- to raise money and toy donations for local charities.

In 2019, over 800 crawlers attended, with O’Riley’s and fellow pubs having so many toy donations that they lost count. This year, the crowds are expected to be smaller due to COVID-19, but the event will go on. It all happens on December 5 with registration starting at 4 p.m. at O’Riley’s. From there, you will visit some of Pensacola’s great watering holes before heading back to O’Riley’s for raffles and music.

Oh, by the way, wearing a Santa suit is mandatory.

A registration fee plus either a new, unwrapped toy donation for Toys for Tots or a monetary donation to Shriners International gets you a commemorative t-shirt, a 22-ounce stein to fill with drink specials, a chance at a raffle for some great prizes, and admission to the after crawl block party. Like they say at O’Riley’s, it’s going to be one heck of a party!

Crawlers must be 21 years of age or older.

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