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Pensacola sits at the far western tip of the state of Florida, just east of the Alabama line. The city is known for white-sand beaches, a Naval Air Station and Winterfest, its annual jubilee of snow flurries, hot chocolate, elves and Santa. Though the pandemic curtailed some of this year’s wintertime activities, the city of Pensacola is still bringing holiday cheer in a big way.


SEASONAL ATTRACTIONS The Florida Panhandle offers a cool Winterfest in Pensacola. 

Where to Celebrate the Holidays

Who says it doesn’t snow in Florida? At the corner of Pensacola’s Government and Palafox streets, snow flurries fall every night of Winterfest (226 East Intendencia St., Pensacola; 850.583.1365; pensacolawinterfest.org). After throwing a few snowballs, hop aboard one of the city’s two holiday-themed trolley tours. On the Polar Express, families can enjoy cups of hot chocolate and see snowy landscapes. With the Cajun Christmas experience, guests ride a tram to the historic village for a reading of The Cajun Night Before Christmas. Afterward, there’s live music from a jug band, dancing and gumbo. Everyone is required to wear a mask on both tours, and safety checkers will be on hand to ensure social distancing. ’Tis the season!


The historic Seville Quarter in downtown Pensacola features several areas, each with its own fun theme.

Where to Watch for Falling Santas

For a unique Claus-based experience, head to Flora-Bama (17401 Perdido Key Drive, Perdido Key; 850.492.0611; florabama.com), one of the most iconic bars in the state of Florida. Built in 1964 across the Florida-Alabama line, Flora-Bama has made a name for itself with live music, party crowds and wacky events such as the annual mullet toss. Christmastime is no different. Flora-Bama hosts a Santa Drop each December when Santa and a few of his elves parachute in. The event is family-friendly, with games and treats for kids and a full bar for adults. Don’t miss Flora-Bama’s famous Bushwackers, a blend of vanilla ice cream, coconut cream and five types of booze. It’s sure to land you on the naughty list before the day is over.


FORMATION DEMONSTRATION: Naval Air Station Pensacola, home to the Blue Angels, is a great landing spot for military history buffs.

(Blue) Angels We Have Seen on High

Need a brief break from holiday cheer? Pensacola has you covered. In addition to its fine beaches, the city is home to Naval Air Station Pensacola. Founded in 1914, the air station is the oldest in the country. It’s home to the Blue Angels, and all Navy, Marine Corps and Coast Guard aviators pass through its gates. The National Naval Aviation Museum (1750 Radford Blvd., Pensacola; 800.327.5002; navalaviationmuseum.org) is a great landing spot for military history buffs.


Getting There

The drive to Pensacola from Southwest Florida is for hardy road trippers. Plan on a solid nine hours of highway driving. But if you want to skip the trek up I-75, book a private jet instead. Naples-based Elite Jets (125 Aviation Drive S., Naples; 239.900.9000; elitejets.com) offers direct service between Southwest Florida and Pensacola. With luxury aircraft along the lines of the Embraer Phenom 300, nobody will ask, “Are we there yet?”


Photo Credit: Getty, courtesy Winterfest; courtesy National Naval Aviation

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