I went to college in San Diego and like it so much better than Los Angeles! Your situation sounds ideal!
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We have fairly seriously considered moving, but the more we considered places against our criteria, the more we realized where we live is pretty nice, except for high taxes. So far, we’ve decided being relatively near our kids, and having strong friend and medical support (BTW we have no medical issues, we just value choices) outweighs moving/paying less in taxes. If/when kids settle and/or grandkids come along, there’s a chance we would move closer to them.
Not total list of what we care about
Good medical professional availability/hospital
Airport within 60 minutes (could maybe live with 90)
Cultural stuff and green space plentiful
Blue or diverse population
No colder than where we are, but not too hot/humid
If not near family, fairly easy to get too family
Place to run and to ride bikes off the road nearby
Need to have a place you can safely/easily walk for a couple of miles out front door (meaning no living on road that has high traffic/would be dangerous to walk on, or a street that just goes out to said road)
Lots of restaurants nearby
Tax structure considered
Ideally, no more for real estate than home we own, but could go up for right place
Would be great to be on a lake or have Mountain View, or something else to make it special
Need 2 car garage unless something else makes it worth doing without
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@groundhog74 we know happy Maine retirees in Kittery, Wells, York, Portland, Camden, Ellsworth. I think it all depends on what you are looking for. I will say…my Wells and York friends say summers have very congested traffic in their towns because of the summer vacation folks. But they do love where they live.
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Friends of ours have a house in San Diego as well as an old farmhouse in Wells. They don’t spend summers in Maine as it has gotten too crowded for their liking. They go in the fall and even in the winter. They mostly spend summers here in San Diego or travel in the early summer. We have been to their house in Maine and H and I really love that area too.
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Maybe you can talk them into leasing you their Maine home for a month in the summer 
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I think I’ve posted this on another thread, but DH just retired a few months ago, then we visited Massachusetts with DS, DIL and GD. While we were there our house went under contract (first day on the market). We got back to Texas, sold house, moved into an apartment, put a contract on a piece of property in Mass. sight unseen, visited Massachusetts 4 weeks later with DD, DIL, DGS, DGD. Closed on the lot while we were there, and now we are working on getting a site plan and approvals from the zoning board to build a house and ADU. We are back in Texas wishing we could speed things up and move already!!! We had a multi page spreadsheet online that we all contributed to, and that helped us focus on the area we eventually chose. DS’s family, DD’s Family are coming with.
We figure the whole family migration will take several years, but we have taken the specific steps we needed to move us closer to our goal. DH retired, we sold our house, we downsized, we bought a piece of land in new location, lined up surveyor and builder, finished design of home and ADU.
When I get impatient, I have to realize that that is a lot for 3 months!
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Amherst is lovely but likely out of our price range.
We don’t plan on moving. We have an almost paid off house, temperate climate( we see no appeal of 4 seasons) though we would say we do have seasons. A state government that supports abortion rights my husband would prefer it be a bit more business friendly. Ocean and mountains nearby. Both husband and I were born in Ca and have lived our entire lives here. Our entire extended family has stayed in Ca. There is a lot of Ca bashing but for my family and friends we wouldn’t want to live anywhere else. Those we know who have moved miss Ca and now can’t afford to move back.
No desire to move to a foreign country but we enjoy travel. We will do more extended travel when my husband retires.
Two of our kids plus grandchildren live in our city. I’ve been surprised at how many friends of my older children have moved back to raise their family in spite of the high COL. In-laws are still living and about an hour away. We also have siblings nearby.
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About 95% of Maine is not crowded. 
(We hiked for miles on Saturday in a stunning area and didn’t see one other person until we stumbled on a National Fish Hatchery. We were the only visitors but a couple of volunteer workers explained the setup to us.)
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LOL - I am assuming that much of that 95% is no where near a big airport and good medical care (items often on the retiree wishlist)…. and definitely not on the warm winter list. Yet I do see the appeal.
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This is something that we have been dealing with for 15 or 20 years – I see the choice points years ahead and try to get ShawWife to plan ahead with me but she is much more spontaneous and so we missed some of the choice points and de facto have settled into our current situation.
Do you plan on moving when you retire? I did. My only caveat here is that neither ShawWife nor I plan to retire as we both love what we do and can continue it into the indefinite future. We will likely slow down and I will shift the mix of my work more towards pro bono work (and maybe I’ll write another book). We live in a leafy exurb of Boston and both kids have said that they wanted to raise their children here.
I love long views. I had been hoping to move to a place in the mountains and have a house in a warm place in the summer (or a place where the weather is nice all year around like California). About 20 years ago, I wanted to buy a townhouse in Canmore, Alberta (ShawWife is Canadian), but she nixed it as she would no doubt have been the one renting it out when we weren’t using it. Also, I travel a ton for work (all over the world – currently have DC, NY, London, Rejkyavik, Dubai and maybe Bahrain on my travel calendar and used to travel 50% of my time pre-Pandemic) and so could live most anyplace with a good airport but she needs a studio to work in so largely stays at home. Since the Canmore attempt, I took her to look at Boulder, Tucson, San Diego, Denver, Sausalito (we lived on a houseboat for 3 months each winter for 3 winters), etc. None of them appealed much to her, though Boulder might have worked if we could have kept our house in Massachusetts as well, which we could not have afforded at the time. The Bay Area seemed promising as one and then both kids were living there and I had helped start a little tech company there. But, ShawWife sends out her roots deep into the ground and it would be really hard for her to leave Massachusetts.
In the interim, we decided to downsize but to stay in our exurb in Massachusetts and failed miserably at the downsizing part, though did very well at finding a new home. We found a house with a long view (it is on the bend in a river and as I type, I am looking down the river ) surrounded by conservation land and farms but no farther from Boston than our last house. it is so nice (after a major renovation) that I think we are here forever. Alas, it is very large so we have four to five extra bedrooms. It would be a grandkid magnet.
The previous owners had it for two generations and Mom & Dad built an in-law suite right on the river and went to Florida for 6 months and a day to avoid MA tax. Their youngest kid raised her family in the main part of the house.
After we bought the house, ShawD moved back from SF and declared that she would like to repeat that pattern (i.e., live in the main part of this house) when her kids are little (her move back was precipitated by breaking up with her BF, so the family is not imminent). Out of the blue, ShawSon sent me a Zillow listing of a house in our town. He was thinking that he and his wife could buy it and rent it and move to that house when they are ready to have children.
Would you move to another country? We have a house in Canada and, if the politics of the US really went to hell, we would move to Canada (though likely not to that house). I had entertained the thought of living in Mexico or Central America or someplace where the cost of living and of help is really low, but such a move would really be far out of ShawWife’s comfort zone.
Somewhere warmer? So, the only question is whether we find a warm place for winters. We have been going to Florida as ShawWife’s mother has a house there, but both the hurricanes and the political shift have slowed our desire to buy there.
Closer to your kids? Yes, when they were both in SF, but it sounds like they are moving to us.
What are your requirements for a place you’d move to? At this point, I guess I’m still trying to see if there is a place for winters that is a) warm enough; b) not too hard to get to; c) a great view; and d) not crazy expensive. We would also prefer that it has palatable politics – we do not need nor expect everyone to share our views (hard to find many these days as I am socially liberal and fiscally conservative) but I would prefer no militia members on my block (my MIL has one on her block in FL).
Summary. In short, I think we explored various options and ended up moving 2.5 miles from our previous house.
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We’re 20 minutes from the largest hospital in Maine, which we’ve been happy with. The airport is 30 minutes away. Our town is not crowded. 
We do have a restaurant now!
Really, it’s the very narrow strip along Route One that’s crowded, all along the coast. Locals just avoid the area.
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I wish I could move to Canada but I don’t think they would take me. lol
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I’m a 4th generation Californian and you don’t meet too many of us long-timers around. Even many of my relatives have moved away. But whenever I think of leaving when we retire, I do have this sense of pride in being from here—and it’s an incredible place that still blows my mind with its beauty every day. Cheers to sticking around
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Funny, @MaineLonghorn, my brother just pinged me with this listing in Bingham today although I’m not sure why as he and SIL are looking for property in Michigan, and DH and I wouldn’t consider a business or property of this size.
What can you tell me about Bingham that I can relay to him?
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It’s beautiful, right on the Kennebec. But the houses are a little run down and there are not many stores or restaurants. My husband couldn’t believe how expensive everything is in the small hardware store. Madison and Skowhegan are the nearest towns with better stores.
Hiking, whitewater rafting, and snowmobiling are all excellent in this area.
It would be great for someone who loves outdoor activities and doesn’t mind being remote. I’m not sure it’s for me.
Oh I just looked at the listing. It’s a B&B my friend and I stayed in a few years ago! My friend kayaked in the river directly behind the place. Very pretty!
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Well typically Boulder winters are much easier than the East coast. Interestingly the past winter was unusually snowy in CO and I hear pretty easy in MA. I bet Boulder real estate looked pricey to you at the time… but wow, it has continued to rise. (I am not in Boulder, but my town as appreciated too just like very many US towns).
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We had our kids young so by the time our youngest goes off to college we would barely be 50. We’ve lived in the bay area all of this millenium and cannot imagine going away anywhere else in the country.
We have a place in SF that we plan to live in once we become empty nesters since its the perfect size (2bd, 2 ba), low maintenance (entire floor in a small 5-unit building), near parks and the water (Presidio area). We like cooler temparatures so the SF fog and chill is something that we enjoy.
We had talked quite extensively about moving to Pac NW or British Columbia but thats a decision we would make only if our kids end up in that area.
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At the time, Boulder RE prices were about 10% less, I think, than the prices where we are. I think $1 MM was the price for a house that was pretty good but not great. Maybe $900K. I assume things have gone up a lot since then in both places. I’m not sure if Boulder is lower or higher, but the house we bought a few years ago here appears to have close to doubled in value. I’m honestly unclear why.
And prices in Florida have gone way up too.
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Have thought about this a lot - but no decisions!
We live in the northeast (MA). Would love to find a place warmer for the winter. No to moving out of this country. One kid is close by in Boston, another is in OH. No idea if they will be there a few years from now. Both H and I are still working - retirement is a few years out. Ideally, we’d find a retirement place to move to along with our close friends (almost family). But getting all couples on the same page, same timeline is almost next to impossible. So, who knows what we will do?