Italy and Train Travel

Ryan, A Railpass would NOT be a cost effective travel method for the routes you've listed. You'll most likely be using the Freccia (fast) trains from Venice to Florence, Florence to Naples and Naples to Rome. Those trains require compulsory reservations which are NOT included with the Railpass. You'd have to pay separately for those. DO NOT be caught without a valid reservation, as you'll probably be fined on the spot, and it won't be cheap! If you buy P-P tickets, reservations are included. If you buy the tickets well in advance, significant savings are possible. You might find it helpful to have a look at the excellent Ron In Rome website, as it provides lots of information on rail travel in Italy. For Naples or Sorrento to Pompeii, Naples or Sorrento to Capri and Sorrento to Naples, you'll be travelling via the Circumvesuviana which is not affiliated with Ferrovie dello Stato (Trenitalia). AFAIK, they DO NOT accept Railpasses. You'll have to buy P-P tickets for those trips (they're relatively cheap). Of course, for the trip from Naples or Sorrento to Capri, you'll be travelling by Ferry or Hydrofoil. I don't know whether Railpasses are accepted on the boats? Happy travels!

Good for you for asking BEFORE you bought a rail pass. They almost never make sense for travel in Italy.

First, the private transporatation from Naples to Sorrento and from Sorrento to and from Capri will not accept your railpass. For the remainder of your segmets listed above, these are all high-speed train runs. You can easily buy the tickets for these trains when you arrive. 1-2 days in advance will do it. There are about 30-40 trains a day on each of the runs so you won't miss a train or run into a train with no seats. But, you will pay the full ordinary fare for each of these runs. If you are willing to lock in on the super economy and economy fares for November, you can sign on to www.trenitalia.com, register and buy these tickets right now. Fares can be as low as 9Euro for these high-speed runs. But, you will be locked into trains with specific date and time departures. The Super Economy fares are non-Ech and non-Refun. So you will need to plan your schedule well before going for these tickets.