Indeed. It used to be a lot more bohemian, a lot seedier. It was part of the allure : wannabe pirates, smugglers, former smugglers, illegal immigrants from cuba and haiti (tbh seeing some of them make the 100 + mile journey in a row boat made me admire their American spirit), drug addicts/dealers, crossdressers and prostitutes. But it has become slightly more sanitized over the years; a little more tourist friendly/ somewhat more family friendly.
At this point Key West is no more Gay than anywhere else. Certainly not anymore gay than Portland.
However yesterday morning I got up early and walked over to the convenience store at about 7:30 am. and was immediately approached by a toothless Haitian prostitute. She said in her (real female not a crossdresser though that was common 20 some odd years ago)ghetto pattois: ohh you a handsome white boy.Could you spare a few dollars? " I told her No, even though I knew I had a few dollars in my pocket. Before I could say anything more than "no" she interjects " for 50 bucks I'll suck your dick." So, I reached into my pocket and scrounged up three dollars. I gave her two bucks and told her to have a good day. She says "Hell, you so fine Id swallow too!" So I gave her the third dollar.
But it's "gay" reputation is ONLY "reputation" in 2022. Kind of a schtick that goes hand in hand in with a small section of town. These days gays are fucking everywhere so it doesn't really measure up as much of a mecca.