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Off-Season Pensacola

A gulf getaway that goes beyond the beach

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Courtesy Visit Pensacola

Pensacola is no one-trick pony.  This Panhandle beach town is best known for its sugar-fine sand, lively outdoor bars and cafés, and pristine blue waters that welcome sun worshipers after they cross the three-mile Pensacola Bay Bridge from the mainland, but there’s more to this artsy city than the smell of sea spray and suntan lotion.  In the offseason, on a rainy day, or any time a body needs a break from the sun, there are a surprising number of options to explore. Thanks to Pensacola’s compact downtown, it’s possible to hopscotch through history, dine on tapas and wine, take in a museum or two, and indulge in some retail therapy—and that’s just the first day. 

Read on for inland recommendations... 

History and aviation

Although St. Augustine rightly claims the title of the oldest continuously occupied European-established settlement, Pensacola was the first European outpost in the U.S., dating back to 1559, when Spanish explorer Tristan de Luna planted a flag on the shores of Pensacola Bay. De Luna’s stalwart group struggled through two hurricane-plagued years before abandoning ship.  Known as the city of five flags, Pensacola would be controlled on and off by Spain, France, Great Britain, the United States, and the Confederacy. 

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Get in touch with the city’s roots by taking a ticketed, self-guided walking tour of Historic Pensacola, a three-block village managed by the University of West Florida Historic Trust. The property includes twenty-eight original and reconstructed buildings that date as far back as the early 1800s as well as an archaeological dig revealing remains of early British and Spanish fortifications. Check out the Lear-Rocheblave House to see an example of a Folk Victorian home; the fancier Dorr House, with Greek Revival frippery; and Old Christ Church, a spare, handsome house of worship that happens to be one of the oldest surviving churches in Florida. Entrance to the museums of Art, Industry and Commerce, along with the Children’s Museum and the wonderful T.T. Wentworth Jr. Florida State Museum, is included in your ticket.  Wentworth, located in the town’s former City Hall, is a must-see, with its Trader Jon’s bar installation that pays homage to a famous now-shuttered watering hole and a slew of quirky exhibits, most formerly part of Tom Wentworth’s extraordinary collection.

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“We’re a hidden gem,” said Sheyna Marcey, director of education for Historic Pensacola.  “We want people to come to the beach, but everybody is always surprised when they come see us.” Purchase tickets at the Tivoli High House (there are restrooms there too), also where you can sign up for a guided tour. Better yet, tickets are good for a week, in case the beach calls. 

Courtesy Visit Pensacola

Fans of aviation already know that Pensacola is home to the highflying Blue Angels.  It’s also where every branch of the military trains its pilots. Experience Pensacola’s skygoing history at the National Naval Aviation Museum, where you can explore more than 350,000 square feet of exhibits, including some 150 historic aircraft. Get up close and personal with World War I bi-planes and rare planes like the NC-4, the first flyer to cross the Atlantic.  Try your hand at Top Gun Air Combat flight simulators, catch a Giant Screen film celebrating the magic of flight, and take a peek at the $50 million Flight Academy where kids in 7th-12th grades see if they can soar. Admission to the museum is free of charge. 

Arts and eats downtown

Dozens of small, locally owned shops, boutiques and galleries line the streets downtown. Pensacola’s annual Foo Foo Festival, which takes place in early November, is casting a light on the city’s lively downtown arts and culture community.  A celebration of music, spoken word, and art, last year’s Foo Foo left behind some outdoor art installations, including a whimsical Umbrella Sky Project of colorful umbrellas suspended in mid-air on the side of the Saenger Theater. 

Dipping in and out of galleries and soaking up public art is just one reason to wander downtown. Another is the food: Pensacola has a surprising number of outstanding chef-forward restaurants worth investigating. Chef Blake Rushing, a Le Cordon Bleu Culinary Academy graduate, runs Union Public House, an inviting Southern pub with fun eats like fresh fried pork rinds, a Buffalo Gulf fish sandwich, house-cured charcuterie, and pickle-brined fried chicken that will have you clucking with glee. 

Mari Josephs’ Carmen’s Lunch Bar, a misnomer since you can get tapas and wine until 8 pm, is an intimate spot with outdoor seating and an all-day menu ideal for snacking.  Try the Thai yellow curry crab chowder, smoked salmon deviled eggs, and Spanish pepper poppers with lump crab for starters. 

Restaurant Iron is getting lots of buzz since it moved from the ‘burbs into downtown, and with good reason. Chef Alex McPhail, an alum of Commander’s Palace in New Orleans (no relation to current chef Tory McPhail) dishes up contemporary Southern fueled by local farms and makers.  Definitely sample one of the creative cocktails—the smoked Old Fashioned has bacon in it!—a fine pairing with the duck debris and gravy fries.   Although it’s a bit on the spendy side (entrees in the $31–$42 range), the quality and presentation is downright perfect.  The wild salmon Buddha Bowl with coconut rice, quinoa and sweet potato salad popped with color, texture, and flavors, and is just one example of chef McPhail’s finesse.  

Although Pensacola isn’t a hopping nightlife destination, there are a handful of pubs and live music venues. Old Hickory Whiskey Bar, named for Andrew Jackson, who among his other roles served as the first Territorial Governor of Florida, pours some six hundred whiskeys, both neat and in carefully crafted cocktails.  Seville Quarter on East Government Street is a complex of 19th-century warehouse buildings with different themed spaces used for events and general merriment. Rosie O’Grady’s Good Time Emporium is the spot for live jazz, with shows on the early side. 

Still hankering for water views? On the bayside, Jaco’s Bayfront Bar & Grille is a laid-back spot offering fresh Gulf Coast seafood in casual digs, right on the marina. If you need sand between your toes, take the bridge across to the beach and settle in at Casino Beach Bar & Grille, one of the best of the beachfront eateries, a place to contemplate the surf while throwing back craft cocktails, ahi tuna nachos, shrimp lettuce wraps, and black sesame tempura soft shell crab with roasted corn salsa.  Even when the weather is chilly, the service is warm and welcoming here. Just remember that the Bay Bridge isn’t one-way and that downtown Pensacola is waiting for you. 

If you go: Staying within walking distance of downtown is ideal for exploring Pensacola city on foot. The Lee House, a boutique hotel with nine guest suites, offers porches overlooking Pensacola Bay and a continental breakfast, just a few blocks from town.  The Residence Inn Pensacola Downtown is a less expensive option.  

visitpensacola.com

This article originally appeared in our March 2018 issue. Subscribe to our print magazine today.

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