24 Hours in Pensacola

by Holly Riddle  |  Published September 3, 2018

Being recently recognized as one of USA Today’s best Florida beaches is not too surprising for Pensacola, which has been named Best Florida Attraction, Best East Coast Beach, Best Florida Beach and more. The city and surrounding area is perfect for beach-goers, but, with over 450 years of history, it is also a great pick for those looking to explore culture and cuisine in a warm-weather paradise.

White, sandy beaches and aquamarine waters provide a little taste of paradise in Northern Florida (Photo: @VisitPensacola)

Despite its long list of accolades, the Pensacola Bay area is often overlooked in lieu of other big-name Florida cities like Orlando, Tampa and Miami. Situated on the western portion of Florida’s panhandle, on the Gulf of Mexico, this picturesque gem is home to 18 miles of sugar-sand beaches, where the white shores contrast beautifully against the aquamarine waters of the gulf. Here, paradise awaits.

For those who aren’t easily charmed by a pretty beach alone, Pensacola also offers unique cuisine, from Southern to Cajun fare; a vibrant arts community (it’s the only city from Tampa, Florida, to Mobile, Alabama, to have an opera, ballet, symphony, theatre and museum); and a centuries-long history.

The deep harbor made Pensacola an attractive stopping point for ships sailing between Europe and the New World (Photo: @VisitPensacola)

Pensacola’s history stretches back over 450 years. While those unfamiliar with the history of the New World might think St. Augustine, Florida, to be North America’s first European settlement, the assumption is untrue. Don Tristán de Luna y Arellano, a Spanish explorer, founded Pensacola in 1559, but the area had actually been documented by other explorers as early as 1528.

Once the city was established, it became one of the busiest ports on the Gulf, with its deep harbor providing safe refuge for passing ships. Unfortunately, following hurricanes and other misfortunes, the settlement was abandoned by the Spanish. That is, until the French began to show interest in the land, at which point the Spanish returned and built several fortified towns in the area.


With Pensacola’s long and fascinating history, it makes sense that the city hosts quite a few interesting museums. However, what might not be expected is the wide range of subject matter Pensacola’s museums cover. From local business to high-flying dare devils, there’s a little bit of everything, for everyone.

The T.T. Wentworth, Jr. Florida State Museum (330 S Jefferson St.) is located within the former Pensacola City Hall, built in 1907 in Mediterranean Revival style. The architecture is surely not the most interesting aspect of the museum. In addition to its exhibits on the history of the city, it also boasts a permanent exhibit honoring and detailing Trader Jon’s Bar, a local establishment that became a top tourist destination, known for the eccentric owner’s “tradernomics.”

This museum is worth a stop for both aviation and history enthusiasts alike (Photo: @VisitPensacola)

Pensacola is also home to the National Naval Aviation Museum (1750 Radford Blvd.), where av-geeks can ogle more than 150 aircraft and spacecraft on display, including the first aircraft to cross the Atlantic and four former Blue Angels A-4 Skyhawks. The Blue Angels are a huge part of Pensacola’s claim to popularity, and the annual show draws massive crowds each year. The group is the U.S. Navy’s flight demonstration squadron and the second oldest formal flying aerobatic team in the world. In addition to the Pensacola show, six demonstration pilots travel to shows all over the country each year and have performed for 260 million spectators and counting.

Take a walk in the past, with an immersive tour of historic Pensacola (Photo: @VisitPensacola)

Not your average history museum, Historic Pensacola Village (120 Church St.) is a huge collection of historic structures that extends over several city blocks. Tour an 1805 boarding and gaming house, a French Creole home from Pensacola’s days as a Spanish colony, a church that played a role in the Civil War, archaeological sites dating to the American Revolution and more.


Pensacola hosts many festivals throughout the year, including several dedicated to the arts (Photo: @VisitPensacola)

Pensacola is known as the “Festival City of the South,” with at least one festival each month. Its most popular festival is the annual Foo Foo Fest, 12 days packed with arts and cultural events in November. You’ll find everything from Naval air shows to operas, culinary displays to concerts. Other popular events include the Pensacola Seafood Festival and the Blue Angels Airshow. The city also throws one heck of a Mardi Gras party. Maybe it picked up a thing or two from its nearby neighbor New Orleans?


Each New World Inn guest room reflects the time period and style of one of the city’s historic guests (Photo: Booking.com)

New World Inn (600 S Palafox St.) is situated within the heart of Pensacola’s Historic District. Originally constructed as a box factory, the building has become one of several converted spaces in downtown Pensacola. Restored in 1983, the hotel offers 15 boutique guestrooms, as well as an upscale wine bar, a New Orleans-inspired courtyard and an iconic fine dining restaurant, Skopelos. Outfitted with antique and period pieces, each elegant guestroom is named after a significant historical figure from the city’s past. Even if you don’t get the chance to stay at New World Inn, check out Skopelos, for Mediterranean-inspired Southern cuisine, well-regarded across the region.

The Pensacola Grand Hotel (200 E Gregory St.) is another property situated on a historic site — the long-gone L&N railroad passenger depot. The depot, listed in the National Register of Historic Places, was restored and now holds the hotel’s lobby, restaurant, lounge and other spaces. Also downtown, it provides easy access to dining, shopping and cultural experiences. And, the beach is just a short drive away.

The downtown boutique hotel, Lee House (400 Bayfront Parkway) boasts nine gorgeous guest suites with spacious porches overlooking the Bay. Originally an 1866 home, the site captures the charm of a historic residence, while still offering modern luxury amenities. Each suite is homey and intimate, offering a quiet respite you may never want to leave.

Restaurants & Bars

The Fish House specialty? Grits á Ya Ya (Photo: @VisitPensacola)

A Pensacola favorite for more than 20 years, the Fish House (600 South Barracks St.) is known for its fresh seafood enjoyed right at the source, with dockside dining overlooking the bay and harbor. Set in a fantastic location, steps from historic downtown, the restaurant serves award-winning menu items, including the house specialty, Grits á Ya Ya. What is it exactly? Delectable Gouda cheese grits in a creamy sauce, topped with sautéed Gulf shrimp, spinach, mushrooms and bacon. The restaurant has been featured on numerous shows for its unbeatable experience and cuisine and has received rave reviews from famous names like Emeril and Andrew Zimmern.

If it’s soul food you’re after, look no further than Five Sisters Blues Cafe (421 W Belmont St.). The menu and concept are inspired by the chef’s mother and her four sisters, who hailed from Kentucky, where they enjoyed down-home Southern cooking and plenty of blues and jazz to go along with it. Expect all your favorites: fried green tomatoes, Po’ Boys, grits, collard greens, black-eyed peas, fried okra, fried chicken and a healthy helping of fruit cobbler for dessert. You may need an extra mile or two on the treadmill before hitting the Pensacola beaches after this rib-sticking goodness.

One of the state’s best beach bars boasts a long history of catering to hungry tourists (Photo: @VisitPensacola)

For a laid-back, tropical vibe, plus plenty of awesome events throughout the year, head to Casino Beach Bar & Grille (41 Fort Pickens Rd.), voted one of the Top 10 Beach Bars in Florida. Formerly home to a popular resort in the 1930s and ‘40s, the spot is now claimed by a restaurant that bears the same name. This local hotspot serves an array of vacation-worthy food, including peel and eat shrimp, wings, fresh seafood, fish tacos and more. Plus, the drink menu can’t be beat, with cocktails perfectly suited for the beach-livin’ lifestyle.

Beachside dining doesn’t get any better than this (Photo: @Innisfree Hotels)

Enjoy fresh seafood (no freezer here, people!) and open-air, dog-friendly dining with a side of Southern hospitality at Red Fish Blue Fish (5 Via De Luna Dr.). The menu includes modern takes on regional favorites, like pimento cheese dip with pickled jalapeños and flash-fried pita chips, a fish dinner with a side of jasmine rice and edamame succotash, and barbecue chicken with sweet potato hash and street-style corn on the cob. Top it all off with a 32-ounce Blue Fish Bucket — a concoction created with fruit rums, juices, blueberry pomegranate puree and Sprite.


Pensacola provides an array of shopping, whether you prefer intriguing antiques or luxury designs. If your interest lies more toward the former, there are two outlets to add to your itinerary. Located on the western side of the city, the Rusty Relic (3955 W Navy Blvd.) is described as “fun and funky.” Be forewarned: you could easily spend an entire day exploring its seemingly endless array of vintage antiques. From art to weaponry, furniture to tchotchkes, you’re sure to find something that catches your eye at a great price.

Another favorite antique shop, located on the north side of the city, is Miles Antique Mall (5109 Bayou Blvd.). The largest antique mall in the state is home to more than 500 vendors across its 65,000-square-foot showroom. Beyond antiques and vintage items, products include new furniture, local art and boutique clothing.

If you’re staying in and sticking to downtown Pensacola, you’ll hardly experience a shortage of shopping options. Palafox Street has been named one of the “10 Great Streets in America” partly because of its main street appeal and wide array of shops, offering gourmet food items to jewelry.

Two must-visits for foodies are The Bodacious Olive (407 S Palafox St.) and So Gourmet & Kitchenry (407 S Palafox St.). Located in the same building and sister companies, the two are right on the corner of Palafox. The Bodacious Olive offers an assortment of artisanal olive oils and balsamic vinegars, fresh-made pastas and bread, and gourmet salts and seasonings. Upstairs, So Gourmet & Kitchenry sells all the culinary supplies you could need for your own home, but also hosts experiences at its wine shop, cheese counter and culinary instruction kitchen.

Belle Ame’ (112 Palafox Place) is yet another unique shop on Palafox. This small family business produces bath and body products in small batches, a perfect gift for yourself or your favorite Lush lover. Just down the street, fashionistas will find adorable and stylish designs at Indigeaux Denim Bar & Boutique (116 Palafox Place). Clothing ranges from summery dresses and upscale looks to casual denim and you-won’t-find-it-anywhere-else accessories.