The winter season in Pensacola has so much to offer. From pristine beach walks to holiday festivities, it's a fabulous time to visit. Read the itinerary below for how to spend a perfect winter day in Pensacola.
8:00 AM Stroll on the beach and Explore Gulf Islands National Seashore: Who said you can’t go enjoy the beach in the winter? Winter is actually the best time for shelling. Grab your coffee and a light jacket and walk along the shoreline on Perdido Key and see if there are any hidden treasures washed up from high tide the night before. You may even find a sand dollar if you’re lucky. Check out the different beach public access points in Perdido Key. After your beach walk, head over to Johnson Beach on Gulf Islands National Seashore. Named after Rosamond Johnson, Jr. himself, this area of Gulf Islands is filled with history and adventure for you to explore. He was the first US Army soldier from Escambia County to die in the Korean War. While you're at Johnson Beach, check out the bike path, kayak launch, various boardwalks, and pavilions.
12:30 PM Lunch in Perdido Key: It’s time to head to the Flora Bama Ole River Grill to enjoy lunch in Perdido Key. The Flora Bama is an icon and a must do on your winter day in Pensacola. Once you’re done at lunch head across the street to the Flora Bama Lounge, Package, & Oyster Bar to grab a drink and enjoy some live music.
2:00 PM Big Lagoon State Park: Stop on by Big Lagoon on your way to Downtown Pensacola. You’ve got to check out the Big Lagoon Observation Tower for some amazing views. Climb to the top and don’t forget to snag a selfie up there! You may even see a bird or two, so keep your eyes peeled.
4:00 PM Downtown Pensacola: Enjoy Palafox Street and stop in the shops, art galleries, restaurants, and more. Rusted Arrow Mercantile is the place to go for your cute Pensacola-themed gifts. Innerlight Surf Shop also has tons of beachy merchandise for the outdoor lovers. If you’re feeling more of a boutique style, stop in at Scout and peruse the latest fashion trends. Did you know that Artel Gallery is free to enjoy? Stop by and check out the art on display (you might even want to take some home with you!)
6:30 PM Dinner in Downtown Pensacola: After your afternoon of shopping and snacking, it’s time for dinner. There are so many options for dining in Downtown Pensacola. If you’re looking for a more upscale experience, head over to Jackson's Steakhouse for the perfect cozy vibes and warm food. At Angelena’s Ristorante Italiano, you can grab an Italian dish to cap off your evening. Union Public House is a crafty southern pub and is a great spot to enjoy. Looking for a more chill spot to go? Graffiti Pizza, Papa’s Pizza, O’Riley’s Irish Pub, and The Dog House are all phenomenal spots to grab a bite.
8:00 PM Nightlife, Drinks, and Entertainment: What’s next? Perhaps some live music and a cocktail? Well, you’re in the right place. Some of the bars in Downtown Pensacola do a holiday theme which is always a fun way to get in the festive winter spirit. Stop over at The Kennedy, The Well, or Garden and Grain for that tasty cocktail you’re looking for. More fun spots include 200 South and Play, so you can enjoy those arcade games. Seville Quarter, Vinyl Music Hall, and The Handlebar are all fabulous live music venues. Wherever you end up in Downtown Pensacola, you're sure to have a fun time.
Pro Tip: If you’re lucky, you might end up in Pensacola during a fun seasonal event. There are several going on during the winter season, so be sure to plan accordingly to hit whichever event you'd like to attend. From Winterfest, to Pensacon, Mardi Gras, Sun Belt Basketball, and more, there's always something to keep you coming back for more.
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