My partner same-sex domestic partner and now husband of over 20 years and I are considering retirement to Hilo, HI. We have chosen it partly for its tropical location and partly for the fact that it is just about the only part of that state that is anywhere near affordable. We also have relatives in the administration of the University of Hawaii at Hilo. We have visited there several times from our life-long home in Pittsburgh. While there is a GLBT community there it is rather weakly organized and barely present as compared to even medium-sized mainland cities.
We are also considering looking into one of the GLBT retirement communities on the US mainland, but have been finding them rather expensive.
Stonewall in Boston originally had the idea of doing fairly upscale housing, but then the lousy economy hit and the idea was shelved. They are running a very successful "lifelong learning" program in which members themselves lead a great variety of programs. It's especially great for people who are retired (as I am not) because many of the programs occur during the day.
I think Portland, Oregon has a progressive gay community. I belong to First Unitarian Church which is proud to be a Welcoming Congregation. Portland would be a great place for LGBT people: lots of public transportation and cultural events. Co-housing is also a god alternative. There are at least five co-housing communities in Portland, and all are welcoming of LGBT persons. Naturally, I would recommend the co-housing group I am a member of: Daybreak Cohousing.
I can sympathize that it's alluring to yearn for both a better climate and a welcoming social community. But of the two, the social community is a lot more important than the climate. As good as it feels to find others you can relate to, finding a mix of people of all ages and cultures is incredibly energizing.
I'm always reminded of one of my elderly friends who has grown old the way we all want to. He likes to say that so many of their friends have sadly died over the years. His and his wife's reaction was, "So we went out and found younger friends!"
It's a great philosophy, I think. We watched our MIL get increasingly depressed as her tight social circle fell apart. People moved away, divorced, fell ill, or died. She was exactly the same age as the elderly friend I mentioned above, but what a difference in the way they approached life!
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