Discover Gay Florida :: Pensacola

by Mike Halterman
Sunday Jul 7, 2013

The city of Pensacola, on the northwest Gulf Coast of Florida, has a long and storied history, dating back to 1559 when Spanish settlers tried and failed to settle the area; they lasted two years before disease and hurricanes killed many settlers and sent the rest back to Spain. As such, Pensacola is touted as "America's First Settlement," while St. Augustine would become America's first permanent settlement by the Spanish six years later.

Over the past 550-plus years, Pensacola has changed hands many times, first from Spanish rule to French, then to British, then to American, and finally to Confederate before becoming a part of the United States again after the Civil War. The nickname of the town is called the "City of Five Flags" for that reason. The historic district near downtown preserves buildings and artifacts from all five eras, with many buildings on the national list for historic preservation.

Pensacola grew slowly from its strategic military importance to many military powers (a naval base is still situated there, where the U.S. Navy's pilots are trained), and for many decades was regarded as a sleepy backwater. In the 19th century, the state of Florida tried to sell the Panhandle area in which Pensacola was located to Alabama, but Alabama rejected it, calling the region "[full of] sandbanks and gophers" and thus not suitable for them! Pensacola's reputation as a vacation spot started around the turn of the 20th century, but really picked up by the 1940s, by which time it was referred to nationally as having "the world's whitest beaches." So white, in fact, that some enterprising hucksters tried to sell the sand to unsuspecting people as black-market sugar, which was being rationed at the time (they didn't get far).

Today, Pensacola is trying to shake off national perceptions of staid conservatism. A "brain drain" that had plagued the town for two decades is finally beginning to reverse itself. The current mayor, a former male model and the first mayor of Pensacola born after World War II, has enticed commercial and industrial brands to base their operations here, and he has overseen a resurgence of the downtown area as a popular nightlife and shopping hub. Today, Pensacola is as vibrant as ever and a place that is growing ever-hip to the gay traveler while still retaining Southern charm.


DGFSolé Inn and Suites

A boutique hotel with modern decor, Solé Inn and Suites is very gay-friendly and is located within walking distance from the heart of downtown. Their pool area is designed in the Old Florida style, and each room offers amenities from luxurious bedding to flat-screen TVs. Make sure you don't miss the complimentary happy hour for guests each day and get to know who's staying there too!

200 N. Palafox St.

Crowne Plaza Grand Hotel

The Crowne Plaza is the tallest building in town. It's really something you can't miss! Situated in between the Pensacola Civic Center and Emerald City, it's a favorite for business travelers, but you haven't seen downtown Pensacola opulence until you tried staying in their two-story penthouse suites on the upper levels. The main lobby of the hotel is a repurposed train depot from 1912, and the grand ballroom seats 500, perfect for pageants or weddings or any party you can think of.

200 E. Gregory St.

Portofino Island Resort and Spa

Not everyone wants to stay in downtown; some people want to be right there on the beach! Trust me, Portofino is where you want to go. It is a resort open to everyone, but it is by far the most gay-friendly of the beach resorts, and where many people stay during Memorial Day Weekend. There's shopping and dining on-site as well as a dream-worthy spa experience. Take care to book in advance in the spring and summer as those are the busy seasons.

10 Portofino Dr., Pensacola Beach


Mardi Gras

Not many people know this, but the oldest Mardi Gras in the United States started in Mobile, Alabama, just one hour to the west of Pensacola by car. Whether you're in New Orleans or all the way down to Pensacola, everyone on the Gulf Coast gets energized over Mardi Gras. (They don't do it anymore, but when I grew up we got school days off to attend day parades!) The yearly "Mall Ball," in which anyone who's ANYONE in Pensacola society hobnobs in our main mall, Cordova Mall, kicks off the yearly festivities, and Pensacola's many krewes have float showcases before the final big night parade on Fat Tuesday. If you can brave the cooler weather in February, it's a fun time to be had by all!

Memorial Day Weekend

The start of the summer circuit party season happens right here in Pensacola on Memorial Day Weekend. Many events happen over the weekend on the beach, culminating in the big Abracadabra show at the Pensacola Civic Center in downtown on the final night. Johnny Chisholm cut his teeth on these events before graduating to Gay Days-sized venues, so he knows what he's doing. For an area that can be conservative depending on who you talk to or where you go in town, Memorial Day Weekend is Pensacola's second-largest yearly event based on profit earned.

Fiesta of Five Flags

Pensacola's history is long and very rich, so what better way to relive the beginnings of the town than to show it off in two weeks of events? Immediately after Memorial Day, in the first two weeks of June, Pensacola goes retro, 16th-century style, to recreate the founding and attempted settlement of the town. The event has gone on for nearly 50 years and includes an authentic period-style boat show and a classical ball with elected court. History buffs will love it.

Blue Angels Air Show

This is where the money is. When the famed flying Blue Angels are not touring, they are based in Pensacola and can be seen training during the winter months. They come home from their yearly touring schedule in early November and have a large open air show, which brings thousands to Pensacola Beach and millions in revenue to the city. Sadly, with this year's sequester drama and the resulting budget cuts, 2013's Blue Angel show is in doubt. But keep an eye and ear open; if it's on, it's a sight to behold.


Emerald City / The Other Side

The oldest continuously-operating gay bar in town, Emerald City was opened 15 years ago and is owned by Johnny Chisholm, whom people may know for also owning Oz in New Orleans' French Quarter and for his "One Mighty Weekend" events during Gay Days in Orlando. The bar is split up into two sides, "Emerald City," which has a dance club atmosphere and drag shows on the weekends, and "The Other Side," a well-lit, oak-finished bar perfectly suited for happy hour, with music videos playing at a soft volume in the background. The drink and drown events and drag shows hosted by Lauren Mitchell are legendary. The Other Side is open from 3 p.m. to 3 a.m.; Emerald City opens its doors at 9 p.m.

406 E. Wright St.

The Roundup

The Roundup has existed in various incarnations and locations off and on for decades. This bar skews slightly older, but not exclusively; anyone who likes very masculine men, bears, or leather are very welcome here. Karaoke nights tend to bring in a more mixed crowd. In my opinion, The Roundup serves perhaps the strongest drink in town, so you will not be disappointed if that is your preference. The atmosphere is relaxing, if a bit dark. There are big crowds especially on the weekends.

560 E. Heinberg St.

The Cabaret

The Cabaret is the newest gay bar in town, opening in 2009. The owner, formerly a longtime employee of the massive Connection complex in Louisville, Kentucky, knows his stuff, and it's a rare day you won't see him in the bar talking to customers or upgrading something inside the bar. The decor is elegant and upscale and the sumptuous wooden bar just makes you feel fancy by looking at it. It's a great place to bring a date if you want to talk and actually hear one another. The weekends can get busy, and it's easy to see why, with prompt waiter service and house DJs playing Top 40.

101 S. Jefferson St.

300 S. Alcaniz St.|


Want a beer and some good food? Hopjacks is the place to go. Famous for their long beer list (over 110 at last count), pizza (where else are you going to find crawfish or filet mignon as toppings?) and their "Belgian fries" fried in duck fat, Hopjacks has become not just a local institution, it's become a moneymaker for the entire downtown area (they've opened up other endeavors, such as a burger bar, further down on Palafox Street). If you love live music, Hopjacks supplies that every weekend.

10 Palafox Place

The Leisure Club

LGBT-owned and operated, The Leisure Club is a chill urban café where businesspeople and "ladies who lunch" can sit in happy, warm colors and partake not only in freshly-made paninis and other sandwiches, but also in dozens of wines. It is also the only eatery in downtown Pensacola that serves Intelligentsia brand coffee. A little pricey for Pensacola, you do get what you pay for, and the service and attention to detail are top-notch.

126 Palafox Place


McGuire's, an Irish pub/restaurant combo, is as much an integral part of Pensacola as the five flags. There are so many things the restaurant is "best known" for, so where do I start? Their steak and roast beef selections are some of the best in town, and the variety of hamburgers on offer will please anyone with a picky palate. Every evening, men in kilts walk through the restaurant at certain intervals playing bagpipes. And yes, who can forget almost the entire length of the walls and ceilings covered by dollar bills, signed by tourists and locals? It may be a tad kitsch but if you want the true Pensacola experience, you have to go once.

600 E. Gregory St.

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