Discover Gay Florida :: Pensacola
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. www.soleinnandsuites.com
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. www.pensacolagrandhotel.com
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 www.portofinoisland.com
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.