After having my car hit 3 times in one week driving in Italy, I swore this time I would do it without the car. So I tried rail. I had almost as much trouble with rail as with driving.
First, never, ever, ever buy a Eurail pass for Italy. It is way too expensive compared to the train fares. Its a good deal in Switzerland, so I bought one for Italy before doing the research. It became a running joke in Italy - every single Italian rail employee we had to show the pass to told us we should not have bought it. So not only did I pay too much, but I got reminded of it twice a day.
Second, all but the smallest and shabbiest trains require advanced reservations, but these reservations are nearly impossible to make if you are not Italian, because the rail site has some kind of weird block on most all American credit cards (much about this around the Internet). This means that I can't just have get-on-the train and go flexibility, I have to pick a train I want to use in the future and then stand in line at a rail station to purchase the ticket or reservation. Lines do not move fast in Italian rail stations.
But the classic story comes from my minor infraction of rail policy that ended up costing me money. I don't know if this is just government or if it they have a lot of problem with cheating. Apparently, each day you are supposed to fill that days date in the next slot on your Eurail pass before you get on the train. I forgot to on one trip, so the conductor insisted I owed a 50 euro fine. Seriously. I said, let me add the date right now, but she said no. They had a couple guys lined up to throw us off in the next random Italian town if we did not hand over the money (reminds me of this story in England).
I will say, once I calmed down, that in retrospect the lecture from the Italian state employee on why it is important to follow every single rule and to trust our betters in government that all the rules are for a good reason was almost worth the 50-euro price of admission.
It took me a while to figure out what they were afraid of -- I suppose if you did not write the date in advance, and the conductor never came by, you could get an extra day of travel. Of course, I had paid extra money for a reservation on that particular train, so it was unlikely I was gaming the system (another reason not to get a Eurail pass in Italy, you still have to pay extra for nearly every train). And it seemed odd that on a 2-hour train ride they thought it a real risk no conductor would come by, though on the very next day we took a 2-hour ride and there was no conductor, so I suppose it is possible.
In that latter case we were in a car where the AC failed on a hot day, and of course it was the only train we rode on the whole trip where the windows did not open. No conductor took my ticket, but one did stand at the end of the car the whole trip turning away anyone who wanted to get an open seat in the next car -- after all, we were assigned a specific seat and sitting in another would be against the rules.