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Eurail passes

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Planning a trip for three weeks to Italy, flying into Rome for a week, then traveling down to Sorrento with a few side trips to Naples, then over to Venice for a couple of days then off to Florence. Then we have booked a tour from there which they will take us to Siena for a few days and from there a train to Cinque Terre and then finally back to Rome. Just a little confused about the train system & which tickets to purchase , is it better to buy while there? Or before I leave the States?
Also: if I purchased the selectpass 6 days for 2 months .would this be sufficient enough to get me to the above without requiring more tickets?
Thanks for any help I can get.

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