Good question, b/c I literally can't choose. My husband and I both have lived in, traveled to, and are attached in some way to so many great locations; and both dislike where we live (for his career). But now that we are attempting to figure out where to go for his retirement, we are really struggling and finding that there are big downsides to nearly all our ideas, and practical considerations are likely going to almost totally dictate where we go.
If money was no object at all, I've flirted with the idea of living on the Big Island of Hawaii, in one of the small towns near Melbourne or Sydney, in San Diego or Monterey CA, and in Santa Fe NM (or just bumming around Europe, which I've never visited, slow travel style). I also am very attached to places in the Caribbean (though I wouldn't want to live there unless I had a job I liked), and to Northern California (Mount Shasta area). I also really liked Virginia, where my sister lives.
But honestly, if money was no object I'd most likely be a snowbird (or as my husband says, Neotropical migrant), with one house in Wisconsin or the Pacific NW and one in Tucson AZ.
Realistically, we looked at Oregon (very expensive for retirees, gloomy weather, full of his relatives that he wants to avoid), Tucson (was our default option for years until the western states started fighting over water issues b/c of the megadrought, and AZ looks to get its water allotment cut back to something like what it was using when I first started college there, back in 1990! only with a much bigger population). Plus real estate remained super affordable there until about 3 years ago, when it shot up incredibly. So that's looking much less likely.
Our friends are scattered all over, but we are considering Silver City NM realistically, b/c of several friends there and it being still fairly affordable. But again, megadrought and water issues, plus wildfire risk (yay). Also a pain, the need to travel to Tucson or Phoenix for specialized medical care (which I need a fair amount of). Still, my friend who lives there does that every 2-3 months, and it's not like it sucks to go to Tucson, so, this remains a live possibility.
My one sister is in Virginia, which is beautiful and probably affordable, but my husband has negated anything in the Southeast on principle. My other family is still in Wisconsin, so that's a live possibility, but the winters fucking suck there. Plus, it's crazy expensive around Madison, but the property up north is starting to climb in value too (and is likely to do even more in the coming decades as rich people flee climate change related weather issues). On the other hand, no pending climate-change-related water shortage or dangerous heat waves on the horizon.
We'd likely have a lot more options if we were not also supporting my mother, but housing is going to have to include her somehow in a way that we are either not in the same building, or at least we have very private areas of the house, which means not a small house (apart from this issue, we'd be fine doing a more affordable 2/1.5 type of house. But as it is, it might be that cost of real estate limits us to very few options (or keeps us here in Texas where housing is so cheap). I hope not, though. A few more years will tell, lots of things are currently in flux with exactly how long my husband will work, and also whether I will inherit any share in a valuable property in the next few years, which could potentially change our equation a bit.
So short answer, I'm not sure.
ETA: I realize I didn't include any explanation as to WHY I love certain locations. Answer is, 90% of the time, landscape/nature related. I dislike being in the very conservative social/political area I'm in, but I could tolerate that if the land wasn't such a bleak disaster zone (plus, no public land here!)
