Spain Wait, the same Spain that just dodged a bailout and is still dealing with crushing debt? Yep, that's the one, but austerity measures haven't bitten into the best of what Spain has to offer. This is by no means the cheapest option on the list and, in fact, has the most expensive real estate of any country listed. That said, it's really easy to fit in, with near-ubiquitous English, three-course meals for less than $20 and modern infrastructure that places high value on convenient, punctual rail service. Combine that with teeming culture and tons of ways to pass the time and Spain can be a great fit for retirees who've already weathered a shaky economy.