Pensacola exceeded my expectations, big time, and is an eye-opening foray into Southern U.S. history, culture, and birthright diversity. Although Pensacola is in dispute with Jacksonville and St. Augustine about which is America’s first settlement, this city has deep roots that stretch to back to 1559. Five flags have flown over the city since then, each molding its architecture, cuisine, and old-meets-new area attractions—including an epic, now-retired military base on what could be a resort island.
Florida has many different personalities—Pensacola is WAY closer to Alabama (20 miles) than Miami (700 miles), so the locals blend Deep South with a New Orleans-style Creole charm. This part of Florida is absolutely nothing like South Florida’s retired New Yorker scene. It’s also a tale of two cities. Downtown Pensacola sits on the mainland. Nearby, Pensacola Beach is a sugar-white Gulf-of-Mexico sandbar that’s a short overwater causeway ride away. As you’ll see, the Pensacola Bay area certainly has no shortage of salt-water-nurtured nature, activities, and gumbo. And, the locals are as friendly as they come—where Florida’s Wild West meets New Orleans cool (which is only a three-hour drive).
The main drag here is called Palafox Street, which serves up a bounteous mix of shops, restaurants, bars, boutiques, and galleries. It’s also draped in large droopy trees, culture, and history. A huge pedestrian median divides the street and sets up a lively three-block marketplace every Saturday where organic farmers and arts-and-crafts vendors sell their goods.
Half of the fun in dining is atmosphere and Polonza Bistro, well placed on Palafox, has plenty of it. The charming space embraces the history of Pensacola, as Polonza earned its name as a term the Spanish explorers gave a nearby bay. Homestyle comfort options include their Toad in the Hole, a regional mishmash of eggs cooked into sourdough with veggies and cheese. You may need a nap.
Or you can skip the nap and head over to Seville Quarter’s seven huge interconnected barrooms in a former 19th century warehouse. This good time saloon-emporium has two live music stages, one indoors, one out, rain or shine. Across town, McGuire’s Irish Pub is an early 1900s New York Irish saloon with 600 seats and a million signed dollar bills hanging from the ceilings and walls. It’s a bit touristy, but nonetheless, locals also can’t seem to resist it. On the divey side, the Azalea Cocktail Lounge is a step back into the 1970s—to prove it they just banned indoor smoking and have no website.
On the fringe of downtown, 5 Sisters Blues Café celebrates a historic neighborhood that was a melting pot for music, food, and entertainment during the early and mid-20th century. For decades this intersection was the epicenter of African-American businesses and social life. The intersection dates to when the four buildings served as the hub of the blues community—regulars included Louis Armstrong, Aretha Franklin, Ike & Tina Turner, James Brown, Ray Charles, Fats Domino, and Otis Redding. The comfortable, bricky establishment still emanates that old-town charm. Don’t miss Meatloaf Mondays, which includes two sides for $5!
Every vacation needs an academic moment. Pensacola Museum of History is housed in the former Pensacola City Hall (1907, Mediterranean Revival architecture) and has permanent and changing exhibits, including (if you didn’t fulfill your bar fix yet) a moving tribute to the now closed Trader Jon’s, another legendary saloon. It’s adjacent to the Historic Pensacola Village, Florida’s version of an international Williamsburg, where 28 properties share a range of architectural styles including Mediterranean Revival, Renaissance Revival, Greek Revival, Classical Revival, French Creole, and Folk Victorian. History buffs will also enjoy America’s First Settlement Trail, a three-mile marked path through downtown Pensacola and the historic district. Its 20 stops and 70 points of interest date back to 1756.
Although there are plenty of choice accommodation options downtown, I opted to overlook the Gulf of Mexico at the 15-story Holiday Inn Resort Pensacola Beach. These broken-in, relaxing digs include a beachside pool with cascading waterfalls and a 250-foot heated Lazy River—right next to a fun beachfront tiki bar with seasonal live music and crawfish boils.
Typically, waterfront resort strips are not walker friendly, but Pensacola Beach rises to the occasion with dozens of cuisine options, outdoor activities, and party venues. You can park your car and explore this entire beachfront area via foot.
Blue Angels: Blue Angels racing by Pensacola Beach (photo credit: Laura Bogan Photography)
Supersonic jet ballet anyone? Watch the Blue Angels soar on their home turf, as the U.S. Navy’s Flight Demonstration team is proud to call Pensacola home and practices here twice per week. A great way to see them from emerald-green Pensacola Bay is via the Frisky Mermaid Dolphin and Boat Tour.
The phrase if the walls could talk cranks up a few notches at Fort Pickens, an active military castle from 1839 until 1947 that morphed with the times. If there was a hall of fame for gargantuan antique cannons overlooking a gorgeous beach, this place ranks high. The colossal 22-million-brick pre-Civil War fortress looms at the end of a stunning 10-mile sandbar and is the centerpiece of Florida’s only WWII Heritage Site. Unfortunately, Apache warrior and medicine man Geronimo was imprisoned here in 1886 and used as a tourist attraction. Atmosphere-wise, this American citadel rivals any D.C. war monument, and it’s the finale of the renowned Florida Trail. The easily accessible National Park offers a walk on the wild side, overnight camping, pristine beaches, wilderness-like trails, and ranger-led programs.
Enjoy gumbo? The sprawling Red Fish Blue Fish celebrates Southern food on the beach. Also try Café NOLA’s earth-shaking gumbo, as they get Creole food right—when I was there, they were also cranking out fried turkeys for delivery. The down-to-earth Sandshaker bar features what might be the world’s most entertaining live-rock garage with expert sound and a nice breeze. It’s a great place to try a bushwhacker, the region’s famous boozy milkshake. The Paradise Bar & Grill, adjacent to its namesake motel, is another live-music throwback to when this beach was all classic motels.
My initial lure to Pensacola was its annual (autumn) Foo Foo Festival, a 12-day celebration of culturally creative happenings, events, and moments under one banner. Highlights included Jazz for Justice (featuring New Orleans’ Tuba Skinny) and the Pensacola EggFest at Blue Wahoos (minor league baseball) Stadium. The one-of-a-kind barbeque party hosts local chefs, BBQ teams, and backyard cooks—all using Big Green Egg barbeques—from all over the U.S. who share two things: a love of grilling and the joy of giving back (lots of money) to their communities.
A bit further afield…
I noted that Pensacola is very close to the Alabama border and there lies an iconic, imbibing live-music institution, Flora-Bama, which honors that borderline, as this ultimate beach-bar straddles it. This stadium-sized odyssey has five stages with live bands playing from the heart. Originally constructed in 1964, it’s since mushroomed into a classic multi-level roadhouse. Music aside, other events range from bikini contests to weekly church-service happy hours. It also hosts highlights of the 40-years-strong internationally acclaimed Frank Brown International Songwriters Festival. Across the street, the “mellower” Flora-Bama Yacht Club is another massive beach bar/restaurant that’s way down-to-earth and serves up epic gumbo, Caribbean jerk shrimp skewers, and gargantuan Greek nachos.
Roam over to Visit Pensacola and start planning your own history-making vacation. *Photos courtesy of Visit Pensacola except as otherwise noted.