This Seaside City Is Like the New Orleans of Florida

This is a sleeper hit for the ages.

Hugging the Gulf Coast and flanked by sandy beaches so snow-white the shore looks like a balmy blizzard, Pensacola—the westernmost city on the Florida panhandle—often gets overshadowed by its well-trod compatriots: your Miamis, your Tampas, your Orlandos. But what it lacks in Mickey Mouse and South Beach (which frankly might be for the best), it more than makes up for in vibes that conjure dreams of New Orleans or even Salem, Massachusetts—all while Navy jets soar dramatically overhead.

With a population a smidge above 50,000, Pensacola feels like a peaceful beachside gem, with all the benefits of big-city amenities minus the impossible-to-get-into restaurants or horrendous traffic. Much of its architecture and cuisine feels more akin to Louisiana than Florida. A stroll through the downright pastoral downtown feels like moseying through a far-cleaner French Quarter, complete with intricate iron railings, colorful cottages, and restaurants slinging gumbo and hurricanes.

While downtown may channel a mini-New Orleans, other parts of the seaside town feel more far-flung: The Historic Pensacola Village, a smattering of timeworn homes, museums, and cottages that look more like a set dressing for witch trials from The Crucible than your typical Floridian city. It’s all indicative of the fact that Pensacola became America’s very first settlement in 1559 (technically pre-dating attention hog St. Augustine).

Over the course of its subsequent 450 years of existence, all this history, heritage, and character has colored Pensacola into the kaleidoscopic cultural sleeper hit it’s become, offering phenomenal energy, outdoor recreation, seaside dining, and lore unlike anything else in The Sunshine State. Here’s everything that’ll make this your new favorite Floridian city.

Pearl & Horn
Pearl & Horn

Dine on everything from fresh seafood to Waygu beef

For a city with one-sixth the population of Orlando, Pensacola has a staggering amount of high-quality, independent restaurants per capita. This is most apparent downtown and along main thoroughfares like Palafox Street, where seemingly every storefront bustles with diners and barflies.

At the nexus of it all is Bodacious—a community keystone and catchall restaurant-market hybrid for casual breakfasts, candlelit dinners, cooking classes, and stocking up on esoteric olive oils you never knew you needed—where they offer Southern-inspired bites like andouille sausage quiche and creamy grits flecked with Gouda, green onion, and roasted corn. Come evening, it’s out with the fast-casual and in with the hard-to-snag tasting menu reservations for Troubadour, an ever-changing three-course prix fixe experience that sets up shop in Bodacious on weekends, providing an intimate, unique space in which to enjoy things like red shrimp bisque with saffron-braised leeks or Wagyu beef Wellington.

Right next door is Carmen’s Lunch Bar, a warm, intimate space with a lively patio and a U-shaped indoor bar next to the small open kitchen. Coupled with its tapas-centric menu (think Spanish crab melts, buttery soda bread, and Cubano-inspired pork and plantain “pies”), it’s got the feel of a European cafe where patrons take extended wine-fueled lunch breaks.

Pensacola dining
Photo by Amanda Cripe

Around the corner is The Garden at Palafox + Main, a covered outdoor food hall outfitted with airstream trailers, a daiquiri-slinging bar, and all manner of comfort foods. Vendors include BOCA Latin Kitchen, MELT Gourmet Sandwiches and Mac N’ Cheese, and Calavera Tacos, as well as Pearl & Horn—a fast-casual surf & turf concept from the acclaimed local chef behind upscale George Bistro + Bar. Here they sling broiled oysters, lobster rolls, smash burgers, meaty grouper fish & chips, and BBQ shrimp that could hold its own among New Orleans’ finest. After you’ve polished off your oysters, head back into the Garden for a rum-splashed nightcap at the highly Instagrammable Perennial Patio Bar.

With sweeping views of the Gulf just outside, Bonsai on the second floor of the Hilton Pensacola Beach is a stunner of epic Asian-fusion proportions. Hunker down for a sushi-centric omakase and surrender yourself to the chef’s whim, which might just include Japanese A5 Wagyu, tuna matsutake with quail egg and hackleback caviar, langoustine nigiri, and Kurobuta pork belly; essentially, the only way seafood could get any fresher is if you were actually a shark.

The true best way to take in Pensacola’s robust dining scene, though, is with a guided walking tour of downtown Pensacola. Seville Savories Food Tour is the work of Duel Christian, a Pensacola native and impassioned foodie who peppers each of his five restaurant stops with insightful history and charismatic stories. Each stopover exhibits a distinct side of Pensacola, from the modern to the classic, offering snacks like pot roast-filled eggrolls, plump steak skewers, gluten-free meatloaf, pork tacos, and birthday cake fudge along the way.

Photo by Amanda Cripe

Sip seaside cocktails and hit America’s most iconic beach bar

Located downtown, The Well is a newcomer that looks like something you’d expect to find in Miami, resplendent in rich purples, pink lights, tropical plants, and flamingo-clad cocktail skewers dangling over martini glasses. Right next door, sister property Perfect Plain Brewing Co. is a casually chic brewery with oyster saisons, an enormous dog-friendly patio, and a taco truck permanently parked out back.

About 40 minutes west along the beach—and decidedly more casual—Flora-Bama is a decades-old oceanside institution smack dab on the Florida-Alabama state line. Comprised of a veritable maze of bars, performance stages, bingo tables, and billiards, the road trip-worthy mecca is known for its country music and eccentric annual events, like the wildly popular Mullet Toss (the fish, not the hairdo).

Across the street, away from the hordes of people tossing fish fillets like javelins, you’ll also find the far more relaxed Flora-Bama Yacht Club, where live music takes place on the beach overlooking the laguna, and where the shrimp nachos and crab-and-potato “hash puppies” are downright habit-forming. Be sure and try one of their famed Bushwackers, a chocolatey Gulf Coast frozen cocktail tradition that basically tastes like a boozy Wendy’s Frosty.

When you’re done, end your day at Seville Quarter, a sprawling—and yes, historic—New Orleans-esque complex of themed rooms, bars, courtyards, dueling pianos, and a two-story dance hall. It looks a lot like Pat O’Brien’s in the French Quarter, albeit less sloppy and touristy—and, dare we say, the hurricanes are better.

Pensacola Beach
Visit Pensacola Beach

Go from lively bars to laid-back beaches and bayous

Of course, this being the coast of Florida, oceanic outdoor activities are front-and-center—and an apt way to burn through some of those hash puppy calories you’ve stockpiled. Pensacola Beach on Santa Rosa Island, renowned for its sugar-white sand and turquoise-tinted water, boasts 18 miles of pristine shorefront for all your swimming, sunbathing, and splashing needs.

This includes a portion of Gulf Islands National Seashore, some 5,900 acres of land—and 19,000 acres of water—on the easternmost end of Santa Rosa Island. Out here, the hustle and bustle of spring break and mini-golf suddenly go silent, giving way to a place of serenity, pristine nature, and naval lore. The park provides a quiet haven for swimming, dolphin-spotting, bird-watching, biking and hiking along sandy trails, and—most notably—exploring Fort Pickens. A pre-Civil War fortress, this brick behemoth offers a glimpse into the past with derelict rooms, tunnels, and cannons, all of which were used by Union troops, as this is one of the few forts to remain under Union control throughout the war.

Pensacola Beach
Visit Pensacola Beach

Naval history is still going strong today in Pensacola, as the city is home to the Blue Angels. The jets conduct practice flights March through September, and can easily be seen—and heard, thunderously—from just about anywhere on Pensacola Beach. For the big show, visit in July for the Pensacola Homecoming Air Show.

Perfect for when you’re ambling back from Flora-Bama, Tarkiln Bayou State Park is a 4,000-acre wetland and prairie preserve that highlights more of the native wildlife in the region. Known for its rare flora and fauna, including endangered pitcher plants and adorable gopher tortoises, the peaceful park is best explored via an accessible boardwalk through the bayou or with a more immersive trek through the rugged nature trails.

Come nightfall, you have two options: you can go clubbing at downtown gay bar The Cabaret, or you can go glow paddle boarding in a lagoon. For a different kind of neon, try the latter. Glow Paddle is a company that offers nighttime kayaking and paddle boarding on the Pensacola Beach Sabine, a tranquil and shallow inlet of water near the beach. With LED lighting underneath each translucent board and kayak, paddlers are able to float through the darkness under the stars. Look down and you might spot tiny fish following your lights, or a small stingray or two. It’s a special kind of nightlife.

Pensacola Little Theatre
Photo by Amanda Cripe

Come for the festivals, stay for the museums

Another aspect that sets Pensacola apart, especially for a city of this size, is its festivals, museums, and arts scene. Chief among them is the Pensacola Little Theatre, a community non-profit beloved for its year-round programming, educational resources, youth classes, and family-friendly entertainment, all from within the hallowed walls of downtown’s Pensacola Cultural Center. Led by a team of fervent creatives and dreamers, the theater prides itself on diverse storytelling and voices, with musicals, dramas, comedies, and children’s shows.

The Pensacola Little Theatre is a not-so-little part of Pensacola’s thriving cultural core, which is also home to the Pensacola Children’s Museum, the Museum of Commerce, the Pensacola Museum of Art, and the Pensacola Museum of History. If you’ve got time to be wowed by just one, make it the latter.

Housed in a mighty three-story Mediterranean Revival building (the former City Hall), the museum tells the story of The City of Five Flags and illuminates everything from agriculture and Spanish settlement to shipwrecks; conquistador Don Tristán de Luna y Arellano’s anchor from 1559, when he led the European settlement of modern-day Pensacola, is on display front-and-center. The inclusive museum also hosts rotating exhibits that tie the past with the present, like “Queering Spaces: Celebrating Pensacola’s LGBTQ+ Community” and “2000 Men: Black Politicians During Reconstruction.”

Speaking of history: Around the corner from the history museum is the Historic Pensacola Village. Comprised of 8.5 acres and 28 vintage properties, 11 of which are open to the public, this olden district looks more like Salem than Florida, complete with folks dressed up in old-timey garb making tea from local plants and harvesting crops from the gardens. Old homes and structures, like the Julee Cottage, Dorr House, Tivoli High House, and Old Christ Church, can be toured to see what life was like for the region’s earlier residents, and exhibits don’t shy away from the city’s dark past with slavery. The Julee Cottage, in particular, is a small Creole-style cottage named for one of its first owned, a free Black woman named Julee Panton.

An indication that diversity and inclusion are a priority for Pensacola, the city hosts a wildly popular Pride Festival over Memorial Day weekend—so popular, in fact, that upwards of 200,000 visitors descend on Pensacola Beach for the rainbow-clad pageantry, making it the most attended event of the year. Come early November, Foo Foo Festival is a 12-day spree of music, theater, food, and art featuring everything from jazz performances and 3D projections to opera performances, DIY paint parties, the Frank Brown International Songwriter’s Festival, and STAMPED: LGBTQ Film Festival.

For more theater, Pensacola is home to Broadway-level shows, opera, ballet, musicals, comedy, and more, much of which can be experienced at the iconic Saenger Theatre on Palafox Street. For a city of this size, the caliber of its productions is staggering. Truly offering something for everyone, events include hits like Hairspray, Anastasia, and Fiddler on the Roof, along with performances from the Pensacola Symphony Orchestra, sets from Weird Al Yankovic, Beatles tribute concerts, and musical parodies of Sex & the City. All of which to say is that Pensacola is a world-class city of culture, history, and food, in a conveniently pint-sized package.

Hilton Pensacola Beach
Hilton Pensacola Beach

Where to stay in Pensacola

Pensacola is divvied into two main sections: downtown Pensacola and Pensacola Beach, each offering an entirely different atmosphere—while still being easily accessible to one another.

For that quintessential Miami-without-the-road-rage vibe, the Hilton Pensacola Beach is the pinnacle of oceanfront comfort. Rising 17 stories from the sand, it’s a Pensacola Beach icon all its own, with a prime location near the Pensacola Beach Fishing Pier and the Pensacola Beach Boardwalk across the street. No matter your room number, it’s got views for days and water on all sides; even the decor feels aquatic, shimmering with blue tones and multiple pools. If you were any closer to the ocean, you’d need a lifeguard.

Inland, downtown Pensacola boasts a totally different atmosphere, with more quaint B&Bs and boutique properties. The cream of the crop is the Oyster Bay Boutique Hotel, a downtown beauty overlooking the bay. A popular wedding venue and wellness retreat destination, it’s also an all-out luxe abode, outfitted with pearly-white rooms, a huge porch, a lush garden, and enough chandeliers and elegant lamps to furnish Buckingham Palace.

Another downtown option with a boatload of character is the Pensacola Victorian Bed & Breakfast, a historic Queen Anne Victorian that once served as home base for ship captain—and one-time Pensacola mayor—William Hazard Northup. Nowadays, Northup’s loss is the leisure traveler’s gain, as the ornate house just steps from downtown is a bucolic B&B with four guest rooms, a crackling fireplace, hardwood floors, and hearty, home-cooked meals prepared by innkeepers Chuck and Barbee Major.

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Matt Kirouac is a travel writer with a passion for national parks, Disney, and food. He's the co-founder and co-host of Hello Ranger, a national parks community blog, podcast, and app. Follow him on IG @matt_kirouac.