Thriving with new restaurants, music venues, and shops, Pensacola is an oldie, but a goodie.

The landmark Seville Quarter is the historic entertainment complex that became the foundation for Pensacola nightlife.
| Credit: Chris M. Rogers

Pensacola is a comeback story 452 years in the making. Florida's first settlement has a knack for rebounding from hurricanes, war, recession, oil. But its latest challenge is a welcome one: living up to its own great potential. This seaside city—rich with history and entrepreneureal spirit—is emerging as the cultural capital of the Florida Gulf Coast.

You can see the story unfolding in the historic Palafox District, where once-empty 19th-century storefronts in the French-style quarter are surging back to life with restaurants and shops, nightlife and uniquely local culture. This is where the transformation began, where a new urban edge meets Old Florida.

"It's an old city, but it's a new city," says brand-new mayor Ashton Hayward, a Pensacola native who moved home from New York with his wife, An. (They had their son, Aiden, now 7, after returning to Pensacola.) Sworn in this past January, 41-year-old Hayward represents the city's next-gen stewards, young locals who left town for other cities, then boomeranged back, brimming with ideas for moving their hometown forward. "This is just the beginning," Hayward says. "The young people are taking ownership. And that's huge."

Among them are rainmakers Nick Bodkins, 26, and Scott Wheatley, 30, who dreamed up last year's inaugural DeLuna Fest. The beach concert series helped save Pensacola Beach from a tourism nightmare, bringing in peak-summer traffic in October. Tourism dollars were up 28 percent year over year against all odds: oil-black beaches on the national news and competition with free concerts in nearby Orange Beach, Alabama.

What to Do in Pensacola
Downtown, new businesses are popping up like wildflowers after a storm. Vinyl Music Hall anchors a rising nightlife hub with a niche venue for bands too big to play in a bar, but too small to fill the Civic Center. Nearby, you'll find active Skee Ball leagues at a sports-themed "barcade" called Play. Named a James Beard semifinalist for Best New Restaurant in America three months after opening, Elise Coastal Dining is the realized dream of 28-year-old boomerang-native chef Blake Rushing, a Gordon Ramsay protégé. Don't miss his house-cured bacon.

Pensacola Hotels
On the beach a mile from the site of the country's first Catholic mass, Jimmy Buffett opened his Margaritaville Beach Hotel. The 162-room property blends upscale elements (a sleek rooftop pool) with breezy style (hammock-strung palms at the beachfront cabana bar) like a well-mixed umbrella cocktail. Adding another feather to his Gulf-hero cap, Buffett rescued the hotel when the original developer bailed, opening in the crisis month of July. Nearby, a Holiday Inn Resort, with a waterfall-fed lazy river and a thatched-roof bar, opened in February.

The city is taking off. No fewer than a dozen new ventures opened in the past year, in spite of tragic timing. But that's how Pensacola rolls. It earned its "City of Five Flags" nickname after thriving under the Spanish, French, British, Confederates, and United States. Celebrating its 450th anniversary in 2009 with a visit from the Spanish crown, Pensacola proved it commands its own future without losing touch with its past.