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. One example of this increased visibility is that there's now a Pensacola Gay Pride held each June, organized by the local GLBT organization, Gay Grassroots Northwest Florida.
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.
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 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), 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.