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Pensacola Holiday Trail: Check-In to Win $1,000 in Prizes!

It’s both joyful and triumphant! We’ve rounded up some incredible prizes to make your holiday endeavors that much more festive. We’ve compiled all of the holly-jolly holiday to-do’s in Pensacola, all you have to do is take part, snap a photo, and check-in to the Experience Pensacola App when you visit. Each new check-in = 1 entry, no limits!

Download our Experience Pensacola app Experience Pensacola app to start playing

Check in to multiple locations for more chances to win!

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Holiday Contest



The Prize


  • Two-night stay at Margaritaville Beach Hotel
  • Gift Card to Redfish Bluefish 
  • Gift Card to Waterpig BBQ
  • Gift Card to Crab Trap 
  • Gift Card to Nick's Boathouse
  • Gift card to Flora-Bama Watersports 
  • A Nina Fritz Painting
  • A custom gift basket filled with goodies from Bodacious Shops, Innerlight Surf Shop, Waterboyz, and Renfroe’s Pecan’s

Holiday Trail Check-in's

Download Shareables 


Terms & Conditions

Certain restrictions apply. Must be 25 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 ends January 1, 2021, at 6:00 pm (CST). Any registrations received after that time will be null and void. A valid entry includes a check-in with a photo. 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.