I have been to Key West and Ft. Lauderdale. Both might vie for the title of the gayest city but after visiting Gulfport, I would say that they win. Every single business in town flies a variation of the rainbow flag and rainbow benches are in abundance too. I notice those because my good friend Betty builds rainbow benches. Hers are better but I am biased.
Ironically, Gulfport was once a sundown town into the 1950s. You probably know that was an informal policy, though violently enforced that prohibited African Americans from staying within town limits after sundown. Today, it has a nice waterfront on Boca Ciega Bay where a casino is located. The town population is just under 12,000. A law school called Stetson University is nearby.
The town is full of cute restaurants and shops. We ended up eating at the Neptune Grill which was full of locals. I have eaten a lot of grouper on this trip. My wife had octopus which was yummy!