In the two years we've lived in Italy, we've both received numerous emails from readers who are dreaming and scheming a move to Italy, too. Many don't know where to start; others are in the throes of bureaucratic madness and in need of encouragement. We've been happy to offer what insight we can, having walked the road ourselves.
Here is the advice I generally dole out:
*Start at the beginning. Before giving any serious thought to making a permanent move, cash in all your available vacation time for an extended vacation. Spend as many weeks as you possibly can in one location. Rent a vacation home, stay put, and settle into life in that town so you can see what it is really like to live there. Vacationing in a place and living there are two very different things. Get your hair cut. Endure the lines at the post office. Learn the quirky local hours and rhythm. Experiencing daily life may firm your resolve or cause you to realize this isn't your dream after all.
*Take the first step. Seems obviously, but start with the first step, namely bureaucracy. It's infamous, slow, and frustrating...but necessary. If you plan on staying in Italy for more than three months, a visa is required. Start with the website of the Italian consulate you'll need to apply through and research their requirements.*Stay the course. After you've determined the basic visa requirements, keep researching and reading for ways to work through the system. Some consulate agents delight in discouraging you. Others will require paperwork particular to that office (nothing you can do about it but obtain the necessary records). Keep at it; visit Expats in Italy for requirements and advice.
*Follow the footsteps. Get encouragement by reading Expats' success stories. Talk to others who have gone before you to learn how they did it, what they'd do differently, and see where they are today.
*Picture yourself here. Even if you're not making an immediate move it pays to gather information, read memoirs and blogs, watch movies set here, and look at images of Italy to see yourself in your new environment. The Sorrento webcam helps by giving you a window on daily life. There are loads of photo sites that offer up everday scenes, too.
*Keep dreaming. Hold onto that dream! Keep working toward it, envisioning and refining it, and generally stoking the flame to keep it alive. I found The Dream Giver by Bruce Wilkinson to be encouraging; I'm sure you'll find other books, websites and message boards to support and inspire you.