My wife's from all over eastern Wisconsin, but she doesn't like Milwaukee either.
Favorite Italian place would be my grandmother's house. Second favorite would be Mama Maria's in North Hudson, WI. Excellent food, great price for anyone in the Twin Cities area Regardless though, the food at that festival in Milwaukee sucks: It was on-par with Olive Garden.
Favorite city (for what it's worth) would be London, followed by Vancouver. However, I haven't actually been to too many cities in the US (San Diego, Twin Cities, eastern Wisconsin, and WNY would be about it; oh, and various cities in Hawaii and Alaska).
Drinking isn't on my list of fun things to do, so maybe that's why I'm not a fan of Milwaukee, since most of the posts in the thread are talking about beer
Cw