What I wouldn't have given to move to Europe when I was 14! The adventure! The excitement! The opportunity to learn a new language and a new culture!
Have you talked to your son about it? I wouldn't automatically assume that he'd be against the idea.
And after he graduates high school... then what? You will want to be around to offer "moral support" during college, for him to come and visit during holidays and such, no? Then he will be graduating, getting married, you'll want to be close to the grandbabies... etc... Whereas if you go now maybe he'll meet a nice Italian girl.
