Really? Italy and Spain? No offence, but why not tell him to move to Greece as well, while you're at it?
If you really want to move somewhere where you can work in America and take money back, I'd suggest looking at some of the non-Eurozone countries in Europe, particularly Norway and Sweden, as well as Romania, the Czech Republic and the Balkan countries (except Greece). The USD generally does well against the currencies of those countries, though you should definitely do more research before moving. I'm from Romania and I have family still living there, and they tell me that the average salary at the moment is roughly 130 USD a week, and people are surviving off that, they're not exactly living in cardboard boxes. However, with the langauge barrier, Norway or Sweden would be much easier because many people there speak English, which would help until you learned the langauge.
Having said that, it would be much easier for you to just move to Australia and stay there.
You can't up and move to another country just because you feel like. You need to formally migrate, and most countries are closed to migration unless you meet stringent criteria such as required work skills and experience. One answer here mentioned Australia. Well, I suggest you look at the Australian Government's Immigration website and see if you meet the criteria here. This will give you an idea of what other countries will also require of you. http://www.immi.gov.au/migrants/
You might consider Costa Rica, Ecuador or Thailand - some place with a thriving expat community. However, you need to be looking for a place where you can get the paperwork (visa, work permits) to live legally. You also need to consider what language skills you bring to the table and what work you're qualified to do. Check the expat websites for countries you 're interested in; you can find them with a simple search for "expat" and the name of the country.
You need to be aware that as a US expat, you would have to file tax returns in the US as well as your host country and that gets to be expensive.
I would either move to Italy or Spain. Both have really awesome cultures and history. You can learn a lot by living in another country, I definitely want to.