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Train tickets within Italy

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I have now moved on to booking train tickets for my itinerary. I found raileurope.com much easier to navigate. Rail europe has an option to put my entire itinerary instead of individual legs. But when I put Rome airport to Florence, Florence to Venice, Venice to Naples, Naples back to Rome, it suggests that buying a rail pass might be cheaper and more convenient.

My specific questions:
1. Besides cost which may not be much, is it worthwhile to consider a rail pass?

2. Rome airport to Florence: among several options shown, there was one trenialia option which states departure from Fiumicino to Firenze SMN in the afternoon. All other options are first to Roma Termini and then to Firenze. Does this mean that a direct train from airport to florence station (2 hr 14 min) option exists? Or am i missing something?

3. Again from Venice to Naples, there is a direct train option only from Italo. All trenialia options show transfer - venice to bologna / rome and then another train to naples. Italo option is a bit more expensive but seems worthwhile that we dont have to transfer luggage and ourselves to another train. What do you think?

4. Finally, rail europe site shows shipping and handling charges (about 8 eur). I cant understand this, I am only buying train tickets, what is there to ship?

Many thanks.

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