Prague is a good city -- for a tourist -- get out into the 'burbs and it can be "shutter's up" --
I have another choice but dismissed it outright; Dresden. I'm concerned that both Dresden and Prague share something in common, both are former soviet bloc and I suspect both share a certain drabness.
for me it would be a toss up -- it would depend on where in Italy.
Trento. Pics show it's stunningly beautiful. I'll have language problems in Dresden, Prague or Trento so go for beauty?