Be honest. Are you looking forward to the holiday season?

I don’t want to sound like a scrooge, but what we often hope will be a festive time with family and friends can easily become a race to buy this and cook that. Don’t forget to clean the house, find something to wear, order this and wrap that. My head is spinning just thinking about it, and I’ve often fantasized about scrapping the holiday to-do list altogether. Isn’t this supposed to be about enjoying quality time and reconnecting with the ones you love?

Getting away for a simpler, more relaxing holiday vacation seems like a better way to make memories, and Pensacola is ready to welcome guests who want to escape from the hustle and bustle for some carefree fun. Many hotels, condos and vacation rentals offer deeply discounted pricing during the fall and winter. Visitors can take advantage of the low rates as well as smaller crowds and mild weather that is perfect for enjoying the outdoors.

Once you arrive, gather your whole crew for some family photos along the Pensacola Photo Trail. With 15 scenic stops throughout Pensacola, Perdido Key and Escambia County, you can visit popular sites such as Graffiti Bridge, the Pensacola Postcard mural and historic locales like the Pensacola Lighthouse and Museum. Snap photos and use them for holiday cards or simply a #photooftheday.

Couple Taking Selfie at Beach

Thanksgiving in Pensacola

If you visit the Pensacola area for Thanksgiving, come hungry! Many restaurants are planning special menus with reserved seating for Thanksgiving Day, November 28. Enjoy a soulful Thanksgiving plate at 5 Sisters’ Blues Café’, for one, and finish it off with a slice of homemade sweet potato pie. Opt for a traditional turkey plate or any of the standard seafood favorites at The Fish House. We've compiled a list of restaurants below that will be servings this Thanksgiving. Before the big meal, work up an appetite by lacing up your sneakers for the Pensacola Turkey Trot 5K. The annual run begins at 8 a.m. in Seville Square with a route through the streets of Downtown Pensacola. 

Restaurants with Thanksgiving Hours


Holiday Shopping and Activities

On Friday, if you want to shop, you can find Black Friday deals at local stores and boutiques, then the whole family can enjoy the annual Elf Parade. Participants begin lining up at 4 p.m. at the old Escambia County Courthouse at the corner of Palafox and Government Streets, and the parade officially begins at 4:30 p.m. Featuring costumed characters, local choirs and tumbling snowflakes, the Elf Parade invites kids to make their own elf ears and join the fun, walking or riding alongside an alligator “Second Line” brass band through the six-block parade route around Plaza Ferdinand.

elf parade

After dark, look to the skies for fireworks to start the 2019 First City Lights Festival, which illuminates Downtown Pensacola with half a million white lights through January. At 5 p.m., Santa will be on hand in Plaza Ferdinand for a grand Christmas tree lighting and a rare, albeit manmade, snowfall in Pensacola to mark the opening night of Pensacola Winterfest. Ranked the No. 1 Christmas event in the state by Florida Travel & Life, Winterfest features ticketed trolley tours and mini-tours through Downtown Pensacola with musical and dramatic performances along the way.

This year, Plaza Ferdinand also marks the location of Visit Pensacola’s Holiday Cube, located adjacent to the Downtown Improvement Board Singing Tree at the corner of Jefferson and Government. The cube features four different holiday-themed destination scenes and will be set up from mid November until early January. Be sure to snap a holiday selfie in front of it and share on social media using the hashtag #ExperiencePcola.

Ranked the No. 1 Christmas event in the state by Florida Travel & Life, Winterfest features ticketed trolley tours and mini-tours through Downtown Pensacola with musical and dramatic performances along the way.

Singing guides hop on board the trolley and lead the way to scenes from popular holiday movies like “The Polar Express.” Peanuts characters and the Grinch are just a few of the characters riders encounter along the way. The theatre-on-board-a-trolley experience, plus free games and visits with Santa, are available through December 24. Event schedules vary, and purchasing tickets in advance is encouraged.

If you visit in mid-December, you might see Santa parachuting. His grand arrival at Flora-Bama Lounge, Package and Oyster Bar in Perdido Key takes place Saturday, Dec. 14.

Santa and little girl

New Years In The Pensacola Bay Area

Every year, hundreds of brave souls make a splash on New Year’s Day by taking a dip in the Santa Rosa Sound or Gulf of Mexico. Polar Bear Plunge and Polar Bear Dip events are scheduled at Pensacola Beach and Perdido Key.

Finally, wind down 2019 in Pensacola with a night on the town. On New Year’s Eve, begin the evening at the Saenger Theater with a performance by the Pensacola Symphony Orchestra. The symphony's Celebrate the New Year! production features classic tunes with tickets starting at $23. Several restaurants do ticketed parties and events, be sure to check the calendar of events for the most up to date information. If you're looking for a rowdy time, the Flora-Bama counts down the final moments of the year. 

For a holiday season that is as relaxing or exciting as you want to make it, these are just a few of the many ways to make memories in Pensacola. Spending time with the ones you love in a beautiful setting may be the best gift of all.