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Find a New Side of Florida in Pensacola Where dolphins and Blue Angels meet 450 years of American history BY M AT T K I R O U A C The Blue Angels flying over Pensacola Beach
F L O R I DA I N T H E S U M M E R M I G H T T Y P I C A L LY conjure visions of South Beach or family vacations to Disney World, but nestled on the western edge of the state’s panhandle, a seashell’s toss from the Alabama state line, Pensacola is a smaller, underrated city with a flavor, vibe and lore all its own. It ticks all the requisite summer road trip boxes — patio bars aplenty, adrenaline-pumping water sports, miles of sugar-white sandy beachfront — but beyond the sunbathing and dolphin-spotting, it still feels like the most un-Floridian of all of Florida’s beach towns. That’s largely due to its history as America’s first settlement, ahead of even St. Augustine — though later abandoned, it was founded in 1559 by Don Tristan de Luna. It’s such an old city that its nickname, “The City of Five Flags,” is indicative of the fact that Pensacola has been under five flags in its history: Spanish, French, British, Confederate and American. That lore is on full display in Historic Pensacola Village downtown, an 8.5-acre collection of colonial cottages, houses, and churches where old-timey homesteaders and historians offer museum tours, cooking demonstrations and a glimpse into another epoch. Today, though, Pensacola is the kind of singular place where one can step back in time in a historic village or a military fort, then drink a Bushwacker on the beach. Where to Stay
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BBQ Shrimp from Pearl & Horn
Where to Play
With 18 miles of shimmering shoreline, there’s no shortage of oceanic recreation to be found in Pensacola. The main part of the beach, most used for swimming, surfing and frisbee-flinging, is the area surrounding Pensacola Beach Pier, itself a destination for anglers. Lined with casual beach bars, like the nearby Bamboo Willie’s Beachside Bar, you’re also never too far from a mai tai. Farther west on the beach, where commercial development wanes to make way for nature, Gulf Islands National Seashore is a 25,000-acre national park site filled with naval history — especially at Fort Pickens, a brick garrison that remained under
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Pensacola is a tale of two cities, with Pensacola Beach — on the western end of Santa Rosa Island — offering more of that iconic Florida summertime vibe, while inland downtown feels more New Orleans, with its wrought-iron balconies and French Creole architecture. If it’s the former you’re after, the Hilton Pensacola Beach towers like a beachy beacon, rising 17 stories on the Gulf shoreline, with balconies and views from every vantage point — the ocean to the south, and Santa Rosa Sound to the north, with both indoor and outdoor pools in between. For something a bit more quaint, New World Inn is a boutique charmer on downtown’s historic Palafox Street, with 16 cozy rooms across two floors, in a building that once served as a box factory. After being repurposed and restored in 1983, the hotel now includes a French Quarter-like courtyard, a martini bar and an ornate wooden grand staircase lined with vintage Pensacola photography.
