In 2010 my wife and I decided it was time to fulfill a long-term fantasy, and buy a place in Italy. After a bit of research, we decided to check out Le Marche, a region that seems almost totally ignored in the American travel guides, and because of the lack of tourism, we hoped it might be cheaper.
We did a 10 day car expedition, but only a few days in, we happened upon a little town called Pergola, that was almost precisely what we were looking for. Our Italian was a bit shaky, but we got up the courage to go into a real estate office and ask if it was possible to buy an old apartment in our price range. Boy, were we surprised when we were shown a beautiful apartment in an 800 year old palazzo. Well, it took 6 months to come up with the money- I sold a collection of mine, but we came to our new apartment, overjoyed to find that the children of the previous owner had decided to leave everything behind, furniture, kitchen ware, bedding, towels, etc.
We now come for 3 month stays twice a year. We don't qualify for a residence visa, and shuttling back and forth from New Hampshire is a drag, but we love it here so much, and have made many Italian friends- this is the friendliest place I've ever been.
Both my wife and I are able to work while we're here, I'm an artist and composer, and Liz is a virtual assistant with lots of American clients. We don't have a car, but our friends here like to take us on day trips all around this incredibly beautiful region. We're right at the foothills of the Appenines, and only 45 minutes from the sea.
We're the only Americans around, and in the three years we've been here, we've only run into American tourists twice. We'd love to get together with any English speakers who are passing through- Pergola is on the route between Marotta and Cagli, not far from Urbino.
Here's a link to some photos: