Gay Guide to Key West
In 1983 Key West elected Richard Heyman mayor, making him the first openly gay mayor in the United States. He had arrived a decade earlier and opened an art gallery in Old Town. During his time in office the city passed a resolution barring employers from firing people who had HIV or AIDS, which put a town of twenty-five thousand people ahead of every state in the country. Key West had already become the first American city to market itself deliberately to gay travelers in the late 1970s, and in 2018 it elected Teri Johnston, Florida's first openly lesbian mayor.
Duval Street carries the nightlife, and it is concentrated at the quieter end. The 801 Bourbon Bar runs drag upstairs and down, the Bourbon St. Pub complex sits behind it with a pool, and Saloon One is on the same block. La Te Da manages to be a hotel, a bar and a cabaret at once without any of the three suffering.
The guesthouses are the real point of this island. Island House is men-only and clothing-optional with its own gym and sauna, and Alexander's, Azul, Eden House, New Orleans House and the Mermaid & the Alligator run the same gracious, low-key model in restored Conch houses.
Higgs Beach is the swimming, and the Key West AIDS Memorial sits on the waterfront there, listing the names of hundreds of islanders. For a town this size, the scale of it is the point.
Key West Pride takes June, and Fantasy Fest overruns the whole island in October. Key West is four hours from Miami at the end of a hundred-mile chain of bridges, and that remoteness is exactly why it became what it is.