From Bushwackers to bourbon, Visit Pensacola presents the thirsty traveler’s guide to the City of Five Flags

Pensacola is often referred to as the “City of Five Flags” — a nickname born from a long history of colonial occupation. It’s also been called a “little drinking town with a big fishing problem” — which seems apt. Around here, people have been whiling away their days sipping cocktails by the sea since conquistador Don Tristan de Luna lugged the first casks of wine ashore, in 1559. To honor my hometown’s deep history — and its bottomless thirst — I’ve put together a mixologist’s tour of the Pensacola Bay Area. Think of it as a TripAdvisor’s guide — for the thirsty set.

The Settler (5 ½ Bar, 5 E. Garden St.)

This cocktail, the brainchild of master bartender Patrick Bolster, pays homage to De Luna, who founded the first European settlement in Florida in 1559 near Downtown Pensacola. The Settler might draw its name from De Luna, but the drink also nods to other influences. Gin from Britain, sherry from Spain and St. Germain’s elderflower liqueur from France tell the story of the last 450 years of conflict and occupation. It’s history in a glass.

The Old Hickory (Old Hickory Whiskey Bar, 123 S. Palafox St.)

Many titanic figures have passed through Pensacola during the last 450 years, though few loom as large in American history as Andrew Jackson, also known as “Old Hickory.” Jackson, a 19th century military hero who would later ascend to the Presidency, twice captured Pensacola from the Spanish, first in 1814 and again in 1818. He returned to the city three years later to oversee the transfer of Florida to American control and serve as the new state’s first governor. The Old Hickory Whiskey Bar is located just blocks from the Plaza de Ferdinand, where Jackson accepted the territory from the Spanish. Their signature cocktail, named in his honor, features Buffalo Trace bourbon, Dolin sweet-and-dry vermouth and bitters, served in a hickory-smoked glass. Locals voted the Old Hickory the best signature drink in the Pensacola Bay Area in 2014.

Irish Wake (McGuire’s Irish Pub, 600 E. Gregory St.)

Just down the road from the Old Hickory is McGuire’s Irish Pub, famous for “feasting, imbibery and debauchery.” The landmark bar and steakhouse has achieved international recognition for its great food and bizarre traditions, which include inviting guests to staple autographed dollar bills to the walls and ceiling and demanding that first-time patrons kiss a mounted moose head. The pub also features a wide selection of award-winning, house-brewed beers; one of the largest wine cellars in the world; and some of the best pub fare this side of Dublin. Its signature cocktail, the Irish Wake, is a triple punch of Bacardi light, gold and 151 rums, plus Blue Curacao liquor and fresh-squeezed Florida orange juice. It’s served in a mason jar and is so lethal the pub maintains a strict three-drink limit for patrons.

Flora-Bama Rum Punch (Flora-Bama, 17401 Perdido Key Dr.)

A half-hour to the west of downtown lies the laid-back coastal village of Perdido Key, Florida, home to the sprawling Flora-Bama beach bar. The iconic roadhouse, which straddles the Florida-Alabama line, is a true piece of Americana: having been sung about by the likes of Kenny Chesney, Jimmy Buffett, Chris Young and Blake Shelton. The bar is also steeped in tradition with a year-long lineup of quirky events that includes the Interstate Mullet Toss, in April, and the Polar Bear Dip on New Year’s Day. The Flora-Bama’s signature cocktail is the Flora-Bama Rum Punch. The fruity, rum-based beverage is dangerously good and the likeliest explanation for why patrons seem to have such a blast lobbing slimy fish and diving headlong into the ice-cold gulf.

The Bushwacker (Sandshaker Lounge, 731 Pensacola Beach Blvd.)

A half-hour away, back through downtown and across two bridges, lies Pensacola Beach. This seaside community, sandwiched between national park lands on a barrier island, is world-renowned for its natural beauty. Almost as famous as the sand and surf is the island’s signature drink, the Bushwacker. The cocktail — a creamy, chocolaty concoction most often described as a “liquored up Frosty” — was first introduced on the beach around 1975 by Linda Murphy, the original owner of the Sandshaker Lounge. Murphy said she got the idea for the drink after tasting a similar beverage on St. Thomas, in the U.S. Virgin Islands. Pensacola Beach celebrates its iconic cocktail each summer, at the annual Bushwacker Festival. There is no official recipe for the drink, and most bartenders have their own trademark variations, which they guard zealously. Thirsty travelers wanting to try this beverage will have to go straight to the source, which doesn’t sound too bad at all.