Pensacola, Florida is NEVER boring!

By David Perry

Picture a vehicle weighing 66,000 lbs. that can not only fly, but be the most maneuverable thing in the air. Spins! Rolls! Death-dives! At 700 mph! Now picture six of them! No more than 18 inches apart!

Mix, simmer, and stir, you have the Blue Angels of Pensacola. Flying the latest supertechy F/18E’s, the cream of Navy aviators danced and dazzled all around me.

The precision was exact. No wonder J.J. Abrams made a movie about them.

Pensacola’s Multiple Personalities

Coming to Pensacola and not taking in a Blue Angels airshow is like going to Mars and never leaving the rocket. But a lot of the city is like that.

The city is all over the psychic map. And if I missed one part, I missed not only the whole thing, but also how Pensacola brings it all into one camp.

This hit me at the Flora-Bama Yacht Club and Flounder’s Chowder House. Both are local legends, both deliver on good times, both are packed on Saturday nights, both have cocktails from hell, and both revel in a “I’ve got friends in low places” vibe.

They even look alike. But they are on either end of the spectrum, and infinitely complementary.

Decked in faux sharks, penny-dreadful exhibits (“MAN-EATING GIANT CLAM!”), and even a tiki, Flounder’s is all about pushing the suits and ties back in the closet. Way back. The band sang, people played volleyball, I annihilated the beer-boiled shrimp, and the whole space existed in permanent weekend mode.

Flounder’s is in the Pensacola Beach neighborhood, itself the playground of town. I caught a catamaran ride to view a purple sunset and glided across the sound in a transparent LED-lit kayak under the stars. Pensacola Beach is where you do stuff.

Conversely, the Flora-Bama, across the bay on Perdido Key and despite the bras hanging from the rafters (it’s a thing, don’t question it), is where you do nothing at all. In fact, doing nothing is the point.

This is the not-Malibu and un-Miami, where the city exhales. Like Flounder’s, it has cocktails for the ages — the Bushwacker is a lot stronger than it looks — and “the best in flip-flop dining” on the Gulf. When I wanted to do nothing and not feel guilty about it, Perdido was the answer. Then there is Pensacola itself. 

City of Five Flags

The arts are here, the festivals and cons are here, and the history is definitely here; this historic port dates back to 1559, older than rival St. Augustine.

Bouncing from Spanish to French to British to Confederate to Union authority — with Africans and Native Americans (Geronimo was imprisoned here) caught up in the swirl — Pensacola was one of the most cosmopolitan cities of the day. And you would never know it was all blown flat.

Residents still speak of Hurricane Ivan with reverential dread. A Category 3 whopper, Ivan ripped the Gulf a $13 billion new one in 2004, with Pensacola in the middle and creating a city-wide psychic Before and After divide.

But as cleanup commenced, somebody had a brainwave: If Perdido Key is the beach bum and Pensacola Beach is the wild-child, Pensacola would finish the trifecta by being the sophisticate.

Build Back Better

Ivan was the excuse for Pensacola to get pretty. New downtown spaces opened; 2013 saw the opening of O’Riley’s, the Incredible Hulk of Pensacola; mild-mannered Irish pub by day (get the steak sliders), it becomes the rollicking start of any good pub crawl by night (they have a horse tranquilizer cocktail called an Irish Trashcan. I was seeing shamrocks).

Bodacious came in 2012, quickly becoming a local gem for their honey lattes, followed by The Garden at Palafox, a showcase for food trucks. Maker’s Cafe, a pop-up that went permanent, opened last year. 

Then came the Oyster Bay, the premier boutique hotel of Pensacola and the only hotel on the water. With wrap-around verandas overlooking Pensacola Bay, it is a classic Coastal-style manse and where I stayed, cuddling up in endless thread counts in shades of beige and brilliant white.

Luxurious but modest, airy but intimate, authentic but designed to within an inch of its life, the Oyster Bay is a refuge all on its own. 

The domino line continued:  2021 saw the arrival of The Well, the premier cocktail lounge of the city, and Lily Hall, an artsy lodging house cum classy restaurant cum password-protected speakeasy, opened this year. When I said it was my first time in Pensacola; they initiated me with the Deteriorating Conditions, a cocktail that is not only in an actual punchbowl, but also on fire. Oof.

Things are even more creative at Lily Hall (with less combustion). Once the Mount Olive Baptist Church, one of Pensacola’s oldest black churches, the building was derelict by the time Ivan gutted it.

In stepped restaurateur wunderkind Terry Raley. Partnering with Nashville-based Stahlman Hospitality, the two redeveloped the space and made it an anchor of the Old East Hill neighborhood once more in 2023.

Even more impressive, she made me a fan of burnt cabbage. That’s no typo, it’s Cabbage Baked In Embers, and one of the star players at Brother Fox, the Hall’s eatery.

As for the Sister Hen speakeasy in the basement, try the Black Paloma. It’s a tequila concoction spiked with solid black squid ink. 

And Pensacola still wasn’t done. In 2022, the city put its history at our feet — literally. The guide on my phone called it the American 1st Settlement Trail, but locals call it “the Red Line,” a streak of crimson taking looky-loos like me on a three-mile meander through the city’s history.

Along its route are the art and history museums, the latter in the old city hall. Palafox St., the main drag, is a showcase of cast-iron columns and filigree. There’s the Julee Cottage on Zaragoza St.; built in 1805 by Julee Panton, a free woman of color, it is the only surviving example of urban Creole architecture in Pensacola.

East Intendencia St. has some of the best-preserved cottages in town. Imagine Coastal Living and Architectural Digest having kids. 

The Other Coast

I spent my last day on the pier at Pensacola Beach, on the pier looking over water every shade of aqua and some particularly white sand…that squeaks.

Even as Pensacola marches forward, one of its greatest charms is ancient: swept down from the Appalachian Mountains and ground to powder over the eons, after dune of petal-white quartz line the beaches of Pensacola.

So uniform are the grains, they resonate when you walk on them. It was just one more piece of the mosaic. Put it all together, and Pensacola makes sense. And also more than the sum of its parts.

What to know:

Summer (and even fall) in Pensacola is not only hot, it’s humid. Keep those water bottles handy. Also, the Oyster Bay has no restaurant, but gives gratis a multi-day gift-card to Bodacious.