The problem with Subtitle Workshop is that it doesn't handle style tags (<i>, <b>) properly - it often formats the whole line instead of only what is enclosed by the tag. Another problem (not with Italian) is that it doesn't speak unicode. Also, it's a bit unintuitive and forces you to switch between keyboard and mouse all the time because some basic hotkeys are missing. On the other hand, what I really like in Subtitle Workshop is the translation mode (parallel view of original subs and your translation).
I've found
SubCreator to be much easier and faster for creating subtitles from scratch. It's also easier to learn. I use it in 2 passes: first, type in the subs along with the movie (pausing when needed); second, hit CTRL-A for every line to create the timecodes. Now just export to SRT and you're done.