The city of Pensacola, on the northwest Gulf Coast of Florida, has a long and storied history, dating back to 1559 when Spanish settlers first tried to settle the area. Pensacola takes pride in its status as “America’s First Settlement.” Throughout much of its history, Pensacola has been a strategic city for five nations’ armed forces — namely Spain, France, Great Britain, the Confederacy, and the United States. Known as the “birthplace of naval aviation,” Pensacola’s culture has been heavily shaped by the Navy base in town, proudly flying airplanes since 1914. As the 20th century progressed, Pensacola became a hot vacation spot, as millions of visitors walked “the world’s whitest beaches.” Let me tell you about this beautiful city, which is one of Florida’s lesser-known LGBT travel gems.
WHERE TO STAY
Solé 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., 850-470-9298)
Crowne Plaza Grand Hotel
The Crowne Plaza, fifteen stories tall, is the tallest building in town. Situated in between the Pensacola Bay 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., 850-433-3336)
Portofino Island Resort
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, 850-916-5000)
WHERE TO PLAY
Pensacola has a small but thriving LGBT scene. Some of the biggest events geared toward the LGBT community include Memorial Day Weekend, which is the unofficial start of the circuit 
party season in the U.S. Over 60,000 people converge on Pensacola and nearby Pensacola Beach for the festivities. Pensacola Pride, traditionally held the last week in June, consists of an entire week of events, which include a gala and a mini-film festival.
The largest LGBT nightclub in Pensacola is Emerald City (406 E. Wright St.) 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 Jewels of the Emerald Coast, Emerald City’s drag cast, is headed by the legendary Lauren Mitchell. The Other Side is open from 3 p.m. to 3 a.m.; Emerald City opens its doors at 9 p.m.
The Roundup (560 E. Heinberg St.) skews slightly older, but not exclusively; anyone who likes very masculine men, bears, or leather will find themselves welcome here. Karaoke nights tend to bring in a more mixed crowd.
The Cabaret (101 S. Jefferson St.) is located one street away from Palafox Street in downtown, and you’ll find that the decor is elegant and upscale, with a beautiful bar made of polished wood. It’s a great place to bring a date.
WHERE TO GO
Much of the action in Pensacola is centered around three areas: downtown Pensacola; 
Pensacola Beach, located on a barrier island about ten miles outside downtown; and the 9th Avenue area, six miles north of downtown.
The heart of downtown Pensacola is Palafox Street, specifically the portion south of Garden Street. Here you will find quite a few nightclubs, bars, restaurants and bistros, which all have re-energized the downtown area in recent years. Further down Palafox you will encounter the Saenger Theatre, the area’s performing arts center; Seville Quarter, a popular 
nightspot for both gay and straight crowds; the T.T. Wentworth, Jr. Florida State Museum, the city’s museum of history; and the Pensacola Little Theatre, featuring amateur theater and smaller-scale professional productions. Further down Garden Street, you will see the Pensacola Bay Center, which is home to the local hockey team, the Pensacola Ice Flyers. The Bay Center also plays host to national and international recording artists and other major events.
Pensacola Beach is a very popular spot for locals and tourists alike. There are many resorts, condominiums, gift shops and restaurants all along the beach. The annual Blue Angels Air Show flies above the beach each year, and tens of thousands of LGBT people stake claim on their own stretch of beach during the Memorial Day Weekend celebrations. Both of those events are very popular and stimulate the city’s economy.
Around 9th Avenue, you will find Pensacola’s shopping district. Cordova Mall is the largest 
shopping center on the northwest Gulf Coast of Florida, and eight million shoppers visit the mall each year. Down the road there is a new shopping center, the University Town Plaza, which serves local residents as well as students attending the nearby University of West Florida.
In the Warrington area of town, closer to the state line with Alabama, you will find Pensacola Naval Air Station, which has been the national hub for naval aviation since 1914. All Navy pilots must be trained in Pensacola before they are approved for flight. The National Museum of Naval Aviation is open to the public and on display are a number of Navy fighter planes, beautifully restored, from the last century of flight.
For more information on Pensacola, visit the city’s tourism website at visitpensacola.com.
