Myself, I don't want to leave the United States.
And I like a mild climate.
So that narrows it down Hawaii, or near the California coast.
I think a good ten or twenty miles from the beach might be ideal.
For California, I'm thinking somewhere between San Diego and Santa Barbara.
I haven't really narrowed it down any further, but I would if I ran into a lot of money somehow.
...
Where would you live if you could afford to live anywhere?
1) California (LA or SD, coast - NOT bay area)
2) In Europe: Monaco or nearby
(Can’t live in any of these places because my industry is elsewhere, I left California after my studies)
Mexico, mountainous southern Brazil or the Ural mountains. Munich in a pinch.
Norway or Seychelles……
Almost anywhere since it has mountains. Hate flat places.
Northern Italy or western Austria looks great, my roots are there.
But I also like tropical/umid forests and its biodiversity…
Send me to Maldives for a month and then I'll get back to you.
New Zealand looks like a great place. Varied in regions, no venomous snakes like its neighbor Australia and don’t forget Hobbits!
Well, if you have enough money, you can live where ever you want to live.
But I would not be looking for a house in a closed community, with a big fence and a guard.
In that case it would not matter in what country that community was.
Because a lot of those communities are pretty much self-contained like a nursing home (yuck).
I would like to be able to mingle or blend in a bit, which is thougher than you think.
So it would be a country/region with a language I speak or close to that.
And since I HATE cold, that would be in the southern part of EU, California, or Hawaii. Okay, Florida.
If the Brexit comes to a grinding halt, I’ll ad the isle of Jersey to my list.
Almost all of the small tropical island states mentioned have languages or religions that don’t appeal to me, or tropical storms.
Anywhere in the USA except California, New Jersey, New York, Massachusetts, Northern Illinois, Washington DC.
Florida in the Winter , Maine in the Summer
Snowbird!
In my family, we don't like snowbirds because in the Coachella Valley they are usually terrible drivers.
Since we live somewhere relatively hot year round, I call ourselves "firebirds".
Domestic:Vermont, Upstate New York
Foreign: New Zealand, Austria, The Netherlands
Mild weather, English speaking, first world economy and resources, not landlocked-
That rules out just about everywhere except a few parts of the U.S.A.
Chesapeake Bay seems about perfect? Not sure how I would get on with the people though.
In reality, I would likely compromise on the weather and head for the south coast of England because culturally I am British , unless Brexit ruins it.
Interlaken or Grindelwald in Switzerland (canton of Bern).
Sydney Australia.
Vancouver Island impressed me when we drove from Victoria to Port Hardy.
And the ppl were great. We could not get a plain ice tea anywhere, tho, it was always sweetened. 
The Nanaimo Bars were wonderful.
(Of course, it might take me a good long time to get tired of living on the 7th floor of Chateau Lake Louise)
The only problem with living somewhere far from where you presently are, is the lack of family and friends. You have to build up new relationships. There’s the matter of affording to live somewhere, but also affording to leave and visit friends & family whenever you want!
Hawaii is very beautiful, but… if you relocate to live there you’re a Haole. And always will be. Very hard to get accepted.
Also, it’s one thing to visit somewhere and entirely different to live there.
If I had the choice, I’d pick a coastal villa in the south of France. I know the language somewhat, but would of course be motivated to learn it well. If I had an affinity for Italian, I might also pick a coastal town in Italy. CULTURE is a very important part of where you live!
If I could afford to live anywhere… I’d still stay, where I am right now 
I don’t think it’s the best places from all possible aspects, but it’s well balanced. Mostly free(or very affordable) health care and education, yet not insane taxes, mild corruption, it’s safe, acceptably low political correctness (I’m glad we are lacking and behind), still able to tell almost any joke I want without offending or “hating” anyone, balanced gun laws (I have to register, but I can conceal carry), weather is mild, terrain is flat or hilly (no big mountains), I can go “anywhere” I want (there are no “parks”, every forest/field is free to roam). Why I should want to go anywhere else?
Alaska, the further North the better. I’m talking year round snow and a month of darkness in the winter but also 24 hour light in the summer and the northern lights every day.
I like the cold and I’m not old yet.
Not sure, but somewhere on the west coast where I’m closer to better national parks