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Train travel in Italy

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We are planning to backpack around Italy in May. We have an idea of a few places we want to visit but we prefer not to be too planned about it.
Train travel looks good as there are lots of train routes. We will be there for 4 weeks and the longest rail pass is for 10 days which we understand do not have to be used consecutively. However, we are not sure if we really need to buy passes unless they save us lots of money.
The first leg of the journey will be from Rome to Milan - alarmingly,having looked at the InterRail site, the economy seats seem to be booked out already! Not sure what to do in that case.
Most of our journeys will be on regional lines which I understand you do not need to book seats on?
It is all very scary - we have backpacked around other countries and just winged it with no difficulty but it seems to be harder in Italy - or am I mistaken?

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