Courtesy of Steven Gray

Just a few years after an epic flood, the historic heart of America's First Settlement is looking pretty lively.

David Landsel
December 19, 2017

Downtown Pensacola has never been short on vintage charm—we are talking about a city with a serious past, after all, one dating back to the 1550's, when Spanish explorer Tristán de Luna y Arellano and crew first drifted onto these hurricane-prone shores, hanging around long enough to enable Pensacola, years later, to feel comfortable marketing itself as America's First Settlement, and if you don't believe them, you can go ahead and look it up. (Let's save everyone some time—they're correct.)

In the modern age known better as yet another Sunbelt sprawl factory, with its relatively transient population of military families, second chancers and cut-price sun seekers, Pensacola's historic heart often struggled to be noticed. Not that it should have had to beg—from the collection of admirable architecture lining Palafox Street, the city's main drag, to the Plaza Ferdinand VII, which is not a shopping center, but rather an actual plaza in the European sense, named after the then-King of Spain and the site of Andrew Jackson's swearing in as Florida's first territorial governor, old Pensacola offers echoes of New Orleans, sometimes more than just a little. (Head a few blocks up from the plaza, into the residential Seville Square district—you might swear you were two hundred miles further down I-10.)

After years of pushing the boundaries outward, Pensacola is, like so many American cities these days, suddenly all about finding its center. Cruise around the downtown, and you will see encouraging signs of life, everywhere. There's new residential construction, old office buildings are being refitted. Midday on a Sunday, a steakhouse facing the plaza hums with energy. There are lines of people waiting to get into a popular brunch place, there's an all-ages crowd clutching tickets for a show at the historic Saenger Theatre, while around the corner, on Intendencia Street, would-be Insta-influencers are blocking traffic in order to document the eye-catching Umbrella Sky Project, an installation of hundreds of little brightly-colored umbrellas that combine to create a floating canopy.

The looks, it has always had, the potential, too—Downtown Pensacola, these days, feels like a bona fide thing. Your first time dropping by? Here are a few stops that'll have you feeling the vibes in no time.

Perfect Plain Brewing Co. Quite literally brand new, the team behind this ambitious effort have come out of the gate swinging with a cloudy, Northeast-style IPA, a nice Belgian Pale Ale with Huell Melon hops, and a kettle sour named after First Lady Rachel Jackson, who famously spoke (so many years ago) of Pensacola as one of the greatest places she'd ever seen. They're bringing in food trucks as often as they can, and the brewery has already done the odd, fun partnership, for instance a donut and beer pairing with local maker Le Dough. 

Restaurant Iron After working his way up the ladder at some very high profile restaurants in New Orleans (Commander's, August), local boy Alex McPhail came home and launched this delightfully irreverent (but also very fine) Southern spot. Located just next door to the century-old Rex Theatre, Iron is easily one of Pensacola's most interesting restaurants right now, and it's hard to imagine that Iron actually began life out on a golf course, somewhere in the suburbs. A move down to Palafox Street, with its increased foot traffic, says McPhail, all but saved the business. From a highly constructed Caesar salad to a clever chicken and dumplings dish, the food here is often accessible, but never basic; on a recent menu, the New Orleans influence could be seen everywhere, from veal stuffed with sweetbread boudin, to a Satsuma-cured foie gras torchon. 

Palafox Market If you're looking to take measure of the local food aptitude in just about any American city right now, the fastest way is to head down to the farmers market, and Pensacola is no exception. According to market organizers, thousands of people make the rounds here each Saturday (rain or shine, year-round), snapping up fresh raw milk, unusual fruit preserves, organic coffee beans, and top-flight local produce from boutique growers like Coldwater Gardens, over in nearby Milton. There's always something to snack on, too; look for the experimental baked goods from Five Foxes Bakery—at a recent market, they were selling a tongue-tingling ginger-curry cookie.

We’re open today! Ninjas on board ready for action. #taconinja

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Nomadic Eats You probably never woke up craving a salted cod croquette taco, but after you try one at this popular Pensacola restaurant that's actually a food truck, you might just get hooked. Randy Russell, Mandie Soran and Steven Chang are the creative trio behind this mobile operation; their freewheeling menu fuses Latin and Asian flavors with often compelling results. A persimmon and habanero-glazed hot chicken sandwich, served with Serrano pepper citrus slaw on a Hawaiian roll was a popular recent special; they're also big on experiments with Filipino staples (think, for example, chorizo lumpia). These guys have that rare gift for making you want to try pretty much everything they get up to.

George Artisan Bakery & Bistro George Lazi has done it all, really—he left Georgia (the country, not the neighboring state), went to New York, worked at a kosher deli in Queens (Ben's), toiled in the kitchens at Jean-Georges, then later became a corporate chef for Fig & Olive, which allowed him to spend a good bit of time in France, soaking up the culture. So why shouldn't he give it all up, move to Pensacola and open a top-notch French joint on the still-lifeless western fringe of downtown? With wife Luba, who already had roots on the Gulf Coast (her family ended up here after leaving Kazakhstan, years ago), Lazi has created one of Pensacola's sunniest, most likeable places to eat—a French-inspired bakery, café and bistro that's also great for weekend brunch, all rolled into one.

Bluejay's Bakery Justine Gudmondson-McCain began her career out in the Bay Area, later returning home to start her own business—after becoming quite popular for her macarons and cupcakes at the Palafox Market, she's now got this beautiful little spot that's just recently opened, bringing a civilized air to her block of Palafox. The bakery's custom cakes are deliciously clever, not to mention highly photogenic.

Ahhh... this is what I miss from the Gulf Coast!

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Shux Oyster Bar Al Fresco, a Portland-style food cart pod on one of Pensacola's busiest corners, may not quite have hit it as big as it might have considering the location within a stone's throw of, well, pretty much everything people come downtown for, but the anchor, this indoor-outdoor oyster bar shucks a great bivalve—you can get them raw, chargrilled (it's the Gulf Coast way) or baked. Drop by for a half-dozen.