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Train from Naples to Sorrento

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The five of us will be traveling in July on one railpass. We will be going from Rome to Sorrento. I understand we can use the pass from Rome to Naples (I still have to figure out which train to make reservations for - why does this have to be so complicated?) Does the railpass work for Naples to Sorrento? Is that some different train line? Will we have to purchase tickets when we get to Naples? And since the reservation thing is making me crazy - could someone tell me how far in advance I need to reserve? Days or weeks or can it be done right before you get on the train?
Thanks for any help you can give.

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