I've always wanted to go to Italy as well but I've never actually made it. It keeps getting pushed towards the bottom of the list as other trips come up.
A few years ago, I went on a trip to Greece with a travel agent that coordinates small women only trips. It was so much fun. I thought she was supposed to have a trip to Italy but I don't see one on her page, only Greece, Ireland and Maine.
I know you may have your heart set on Italy but I absolutely loved Greece.
if you or anyone is interested. I was figuring out how I could ditch DH and do another trip with her but I don't think he'd go for that