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Venice> CT>Florence>Rome Train Advice

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My friend and I will be traveling in Italy in May and we are starting in Venice then heading to Cinque Terre, We'll then move on to Florence then on to Rome. We have a couple of questions:

1. Should we book trains in advance or just grab them as we go?
2. What is the best way to get from Venice to CT through trains?
3. Would it be better to change the order and go from Venice >Florence>CT>Rome?

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