Pensacola is a little unusual as gay travel destinations go. In late May, the city is the site of Pensacola Gay Memorial Day Weekend Celebration, which draws huge crowds of gay revelers from Atlanta, New Orleans, and other major Southeast and Florida destinations.
The rest of the year, however, this relatively conservative small city in the Florida panhandle has a relatively quiet, even discreet, gay community, although it's become far more visible in recent years, in part because Memorial Day weekend has shown the value of GLBT tourism dollars.
Pensacola does have some very fun gay bars, as well as a number of fairly GLBT-friendly restaurants and cafes, mostly in the city's main historic district, around beautiful Seville Square. One of the mainstays in the Gulf Coast when it comes to gay nightlife is the well-established Emerald City (406 E. Wright St., 850-433-9491), which is a key player in many of the parties and events that take place during Memorial Day Weekend and is also host to plenty of other big parties: Saturday dance parties, Thursday women's events (with "girls only" drinks specials), Wednesday and Sunday "drink-and-drown" parties (with great drag performances at 11:30 pm and 1 am), drag bingo nights, and more. Emerald City has also become quite famous for its annual Halloween party.
In the more relaxed Other Side section of the club, there's a popular happy hour every day. Emerald City has an 18-and-over policy, and although the club has been around for many years, the owners gave it an impressive makeover relatively recently, so it's looking better than ever.
Just steps from beautiful Seville Square and adjacent to the historic Saenger Theatre, the Cabaret (101 S.
Jefferson St., 850-607-2020) is sophisticated but welcoming, a cheerful spot for gay men, lesbians, and friends to congregate during daily happy hours (3 until 8 pm), during the neighborhood's monthly Downtown Pensacola Gallery Night, before or after a show at the Saenger, or during the popular karaoke events on Monday and Thursday evenings. On any given evening, the big draw here is first-rate jazz and piano, with some of the most talented songstresses in the region. The Cabaret has an impressive beer list, and outstanding cocktails, too.
It's just a five-minute drive east along one of downtown's main drags, U.S. 98, from Emerald City to the more neighborhood-y, country-western-inspired Roundup Pensacola (560 E. Heinberg St., 850-433-8482), which comprises a good-size dance floor, a few different bars, and an outdoor deck. Expect a somewhat more mixed-age crowd here than at Emerald City, which is the high-energy hangout in these parts - lots of bears, leather guys, and regular dudes rub shoulders here.
There are also a few ostensibly straight but gay-friendly restaurants and bars in Pensacola, mostly around the historic area near Seville Square. With a vibe the somewhat resembles the New Orleans French Quarter, the rollicking Seville Quarter (130 E.
Government St., 850-434-6211) is a sprawling complex of several bars and dining areas - it's touristy but fun in a Bourbon Street kind of way, and the Palace Cafe serves tasty bar food, including baked oysters, pizzas, and po'boys. The funky bar and vegetarian restaurant Sluggo's (101 S. Jefferson St., 850-791-6501) serves good, healthy food (try the Cajun carrot cakes, or pecan-dusted seitan), and the trendy, retro-cool Leisure Club Coffee Bar & Restaurant (1151 Office Woods Dr., 850-912-4229) is a great bet for artisan-roasted espresso drinks (made with superb Intelligentsia Coffee), fantastic ice cream (the bourbon-burnt sugar flavor earns plenty of raves, and terrific, creative food three meals a day; plus, there's a well-chosen wine and beer list. End of the Line Cafe (610 E. Wright St., 850-429-0336), not far from Emerald City, is another gay-friendly option for great coffee and healthful veggie fare.
And for a romantic evening, or dinner with a few friends, hip Global Grill (27 S. Palafox Pl., 850-469-9966) fits the bill, with its beautifully presented, Southern-inspired fare, including tapas and more substantial plates.
Keep in mind that Pensacola is just an hour southeast of Mobile, Alabama, which also has several fun gay bars and clubs in its downtown historic district.