Such a hard question to answer because it depends on where I feel I would fit in and belong. I’ve traveled but I don’t want to live outside the US. I’ve lived most of my life in the Northeast and am very accustomed to it culturally. There are parts of the US that I would not feel comfortable living in (and it’s not necessarily the “redneck” parts–I can’t see myself living in California, for example, in a million years). I want to be near my daughter and her family wherever they are. I don’t feel that it’s “stopping me” to be near her. Older people need friends and help. Go to a place where you can get them.
We just bought a house (to be built) outside of Tucson. We’ve been in Florida for the last 27 years, are youngish retirees and want a change. We haven’t spent much time out west and want to explore. Our kids are spread out – PA, SC and CA – and have said they will not return to FL. I love the beach so we will be returning to a rental condo (been renting for 7 years) in Cocoa Beach in the summers. That will also enable us to see the friends we are leaving.
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I have a young relative who loves where she lives except for the fact that the Jewish community is very small and predominantly elderly. She plans to move someday to a place with a younger more vibrant religious community.
I don’t care much about religion except that I would never want to live where any particular religion is expected or assumed.
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We have thought very hard about this. We have even tried out some of the places.
I like warm to temperate weather. So, we visited San Diego/La Jolla as it appears to be perfect weatherwise. Our financial advisor lives there. Beautiful scenery. Great seals. Great weather. But, it felt like it would get pretty boring pretty fast.
Marin County. We love San Francisco (great restaurants, interesting art, exciting culture).
For three years, we rented a houseboat in Sausalito (in Richardson Bay). Stunningly beautiful. I’d also consider some other towns there or further north (near Point Reyes, for example). The issues for us would be cost (we’d have to sell our Massachusetts house to buy a nice house there, although we could probably get the houseboat). Abstracting from that, I think we are concerned a) about the smoke; b) the deterioration of law and order in SF under some crazy city administrations (I’m a liberal so this isn’t a Fox News talking point); the homelessness in SF; and c) the tax rate. Both kids currently live in SF. I would consider moving to Sausalito (except for our new house, see below) if they stay there. One has said she would move back to us. The other flirted with buying a house in Portland OR.
Portland actually seems pretty nice to me.
I don’t intend to retire. I love Hawaii, but it is too far out of the way for flying to clients and even for being on a close enough time zone as clients. I loved Sydney, but same problem.
We considered New Mexico. Not warm enough in the winter and pretty dry. In the current post-climate change era, I am afraid most of the West will run out of water.
Canmore AB. Like Boulder many years ago, but Boulder is in the Foothills of the Rockies while Canmore is in the Rockies. I wanted to make an offer on a house there 15 years or so ago. My wife (who is the Canadian in our family) put the kibosh on it (she is the one who takes care of property.
We have talked about Vancouver and Victoria but have never spent much time there.
Just before the Pandemic, we were fortunate to be able to buy an interesting house on an extraordinary lot in sub/exurb of Boston. Grandfathered on a river. Surrounded by conservation land and agricultural land. Stunningly beautiful. But, less than an hour from the airport and probably 30 minutes from Harvard Square (except at rush hour). We bought it at a very good price (I think a few hundred thousand below market). Zillow now says it is worth $1 MM more than what we paid for it but I think this is high. From my perspective, Boston has more interesting people per capita than any other city in the world (except if you are in the arts/restaurant/culture industries. So, I sort of feel we found that kind of place.
I would like a place to go in the winter. My MIL has a place in Sanibel, which I love (scenery is beautiful) but there is not much culture and the restaurants are pretty mediocre. Plus, it will probably be underwater in our lifetime.
I’m kind of wondering where would be a temperate place to spend part of the winter that makes sense given climate change. Any thoughts? Needs a good airport. Culture/food would be desirable, but great scenery would be more important.
We are co-owners of a house on a lake in the Laurentians outside of Montreal. Very pretty in all seasons, but I would sell the place if given a choice and find a temperate place.
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My husband says he would have no problems with the time difference. You just live by the EST and schedule meetings from 6 am to 2 pm HI time. Many mainlanders who come to Hawaii never switch their internal clock… 
That said, if someone is into daytrading, life in HI would suck. Waking up at 3 am local time… 
no thanks.
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I do a lot of work with European companies. So I have calls at 8 am est. Sometimes earlier.
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That would be a problem. 
NJSue - so true. I’m trying not to let “where the kids are” govern the whole decision-making process, but it’s definitely a factor for the above reason. I’ve seen my parents’ during the ‘needy years’ (at the end) and while I absolutely don’t want to burden anyone, I’ve seen how having a local advocate can be a make-or-break benefit. I’m not sure if this goes against the premise of this thread, but it’s a positive factor! lol
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In no order:
Amsterdam - Spending a full spring/summer here is on my bucket list.
New York - I have trouble picking one part of the island though
Chicago - north side
Monterrey
Boston
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Boston is a fun place to visit but I wouldn’t live there. We spent a good bit of time there because my husband’s sister and her family lived in Brookline. We were always very happy to get back to Maine. I would pick Portland over Boston. Great city and you can always go to Boston for visits if you want.
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The Boston area can be great for folks with a fair bit of money (not a constraint for the purposes of this thread) and who are very active professionally and especially intellectually. We are able to live in a beautiful spot in the Boston area and invite over friends and meet their friends, many of whom are doing absolutely fascinating work (biotech, public health, business, lots of incredibly smart academics in an array of fields). I wouldn’t think it would e a great place to retire if you weren’t seeking intellectual stimulation (It’s too cold, crowded, etc. plus the cultural scene is mediocre). But for those with an intellectual bent and are actively inquiring, the burbs have a lot to offer.
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I would just encourage people to go for a long visit before deciding to settle there. I would not enjoy it.
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I think it’s a good idea to spend time (if possible) in a place before moving. It’s easy to think you would like a place but sometimes the reality is different and it’s not your vibe. Or, you might unexpectedly love somewhere you did not consider.
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We lived in the Back Bay for several years and the rest of our years in the Boston area in a lovely suburb. I agree with @shawbridge that it was the most intellectually stimulating time of our lives, and we never again worked or lived among such smart and interesting people. We live primarily in AZ now but bought a summer place in Maine to get back to New England and, partly, renew our Boston friendships with easy access to that amazing city and its environs. But, I agree with @MaineLonghorn that I prefer the Portland vibe now. The great thing is that we can have some of both from this new home.
I absolutely agree that you need to spend (significant) time in a place before deciding to move there. What you might experience on even a lengthy vacation is not the same as, say, renting a place in a town you might be considering. The day-to-day of living in a place will enable you to see what the ups and downs of routine life there will be like. Given that no place is perfect, immersing yourself in a new locale will help you decide just how happy you will be with that place’s imperfections.
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So happy to hear people recommending spending time in a place before committing to moving there. We are doing exactly this. Just signed a lease to rent a place outside of Boston to see if we want to move there long term. We are retired empty nesters with an only child in Boston and want to be near her. I think it will be easier to decide where exactly we want to be and what kind of place we want to live in when we are in the area.
Our dream place to live has always been London. We love visiting there (have been many times). The reality is that it is too far from the US, so we would never do that.
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Houston,Texas
It’s so interesting to see people’s preferences. My husband got a good job offer in Houston fresh out of grad school. I told him I would live anywhere in the world except Houston, and I meant it. The combined heat and humidity in the summer are unbelievable and the traffic is, too. Plus the lack of zoning - a small house can be next to a high rise.
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Oh, wow 
I would do anything to move to Houston,Texas… I’m not ready for the heat and humidity but the traffic is no problem for me since I grew up in Chicago,Illinois for the majority of my life. Its cheaper and lots of job opportunities and I love the state of Texas. The only thing thats stopping me is my family and my finances.
If you love Texas I would suggest San Antonio or Austin. Or Fredericksburg for a small town.
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Best of luck on your transition to the Boston area rental. Are you also keeping your old place/location for a while or selling now?