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I can somewhat, very horribly, speak the language...well, communicate with it, more like. I prefer the cities (although I have never been to Italy), seems more developed and organized than The middle and southern parts of Italy. Also, I'm no so sure about how true this is, but I couldn't live somewhere with some substantial dumb machismo, womanizer demographic, if that actually exists. I also prefer the food of Spain.
Never been to Italy yet so I am choosing Spain though I would for sure like Italy too because I love Italian food so much.
Spain because I feel connected because of language and culture also love Granada and Sevilla.
Italy!
They have the best food, the country is probably the most beautiful in the world, language doesnt seem so hard to learn and i have family there!
Don't care for the country but it has arguably one of the best collection of cities of every size there is with Madrid, Barcelona, and Valencia.
Even small towns like Benidorm are stellar. I don't even want to get into the whole Ibiza thing, it speaks for itself.
I've been to Italy but not Milan. I would like to see Milan, Turin, and Naples. Perhaps one day, they aren't exactly all too high on my bucketlist, whereas Madrid, Barcelona, and Valencia are all towards the top.
I was not impressed with Rome, actually didn't like the place at all. I have a pretty low opinion of the place to be honest.
I wouldn't mind living in either country. I just wish I could speak one of the languages. I couldn't choose between them but I'm more familiar with Italian food and people from living in Australia.
If your criteria is strictly the sheer number historical places and art museums, then Italy.
From a jobs/business perspective it can fluctuate: for example, from the mid-1990s or so up to very recently, Barcelona has probably been a more dynamic center than Milan.
As for practical living, Italy has horrible, horrible bureaucracy and the carabinieri presence at times can feel oppressive, but other times also comforting. Spain's bureaucracy appears somewhat less bad, but with the ETA thing I had an impression of a somewhat oppressive police presence, and in that sense I preferred Portugal, it seemed there is less tension in the air, so to speak.
More on practical living, Italians are very predictable in their daily habits: for example, it seems the entire country eats breakfast at 8AM, lunch at 1PM, dinner at 8PM; I used to go food shopping purposely at 1PM on Saturdays to avoid the crowds at supermarkets; it is almost impossible to eat at a sit-down restaurant from 2PM to 6PM. It seems the entire country goes, or used to go, on vacation in August.
I think the Spaniards are a bit more flexible on those points, certainly the Greeks are.
As a student, retiree or family, it really depends on one's specific interests and personal ties.
On balance, the cost of living is about the same: expensive to very expensive in the big cities; perhaps even a bargain in the provincial towns, provided you have access to income/wealth from outside or are involved in a successful local family business.
Personally, I wouldn't live in Italy or Spain unless I were a student or independently wealthy retiree.
My student days are over (I did both Italy and Spain as a student).
If I were an independently wealthy retiree, and with no other considerations like family, I would live somewhere in Sicily, perhaps the Syracuse or Messina area, or in southern Puglia, the area known as Salentino. If in Spain, Cordoba or thereabouts, but more likely in eastern Algarve.
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