The Pensacola Holiday Trail is Back🎄
Upload your Holiday Cheer to Win Big ✨
We’re searching for the best and brightest holiday magic from around the Pensacola Bay Area.
Browse the Pensacola Holiday Trail categories and stops below. Snap your best photos and videos and upload them for a chance to be featured on Visit Pensacola’s channels. Five people will win big and receive unique Pensacola experiences.
The contest runs through Jan. 1, 2022. Must be 21 or older to enter. Photos must be taken in Escambia County during the contest time. View full terms & conditions.
Prizes
A $250 gift card to Cordova Mall
A beach picnic for four with Organized Occasions
A 1-night stay at the Hilton Pensacola Beach Gulf Front + $25 gift card to Bamboo Willies
A chefs tasting with wine pairings for two at Union Public House
A dolphin tour for four with Ho2 Pensacola + $25 to Bamboo Willies
Photo Categories for the Trail
Photo with Santa
Take a photo with Santa.
Holiday Drinks & Sweet Treats
Take a photo of your favorite drink or a sweet treat when exploring Pensacola.
Winter Fest
The moment you enter Plaza Wonderland in Downtown Pensacola the snow begins to fall. Take a photo of your Winterfest experience.
Shop Local
Never has shopping had the opportunity to give you so much. Now more than ever it’s important to support local business. Snap a shot of you perusing local favorites and your finds for a chance to win big.
Share Holiday Lights
Take a photo of holiday lights in the Pensacola Bay Area.
Shop at a Holiday Market
Never has shopping had the opportunity to give you so much. Now more than ever it’s important to support local business. Snap a shot of you perusing any of the local markets and your finds for a chance to win big.
First City Lights
For all that glitters and glows, Downtown Pensacola is lighting up with over 400,000 lights this holiday season. Show us your holiday cheer for a chance to win big in the new year!
Elf on the Shelf
Share your Sneaky Friends around Pensacola.
Polar Bear Plunge
It’s crisp, it’s cool, so don’t be a fool! While plunging into the Gulf of Mexico might not be first on your to-do list, it definitely shouldn’t be last. Welcome the new year at one of the official plunges, like the one at the Flora-Bama Lounge and Package, or DIY from now until then.
Holiday Fireworks
Send off the season with a bang at one of several holiday fireworks displays.
Upload Your Photos Here
Holiday Trail Check-in's
Terms & Conditions
Certain restrictions apply. Must be 21 years of age or older to qualify. This contest is void where prohibited or restricted by law. Visit Pensacola is not responsible for guest satisfaction at participating properties, or for information technology glitches that may disrupt registration. Each check-in is equal to one entry. The contest begins Nov. 26, 2021, ends Jan. 1, 2022. Any registrations received after that time will be null and void. A valid entry includes a check-in with a photo in Escambia County at a destination experience. Unclaimed prizes will be forfeited if not claimed within 30 days. Other restrictions may apply.
Entry into the Pensacola Holiday Trail constitutes complete permission to Visit Pensacola to use, edit or modify all submissions (including names, pictures, and likenesses) for marketing purposes at its sole discretion.