A general rule is if retiring in a place where you've only been on holiday, rent for a year at least before buying anywhere. We plan to retire in the Mediterranean region. Where exactly will depend on EU and taxation residency laws at that time. To keep our options open, our plan is to buy properties in several countries, including at least one outside the Eurozone. We are leaning towards Sicily because we have grown roots there, but who knows where things will be in 10 years' time.
Very good point. My brother and his wife both dreamed of retiring to the Caribbean (yeah, they're parrot-heads :). When they couldn't afford Key West, they moved to Vieques, a small, less developed island off of Puerto Rico where the housing and general COL was ridiculously cheap.
At first it seemed like the classic old-school Caribbean lifestyle out of a Jimmy Buffett song; but after a couple of years he just couldn't stand it anymore. Constant humidity (you were damp from the moment you stepped out of the shower until you went to bed at night), crazy local politics, and lack of development (including unreliable basic utilities) finally wore them down.
They returned to the States (proper), but it took them a couple of years to unload the house they had bought; local laws & politics had made it very difficult to sell property, especially if it involved a non-local. If they had rented, I think they probably would have moved on a lot sooner than they did.
