Trains!

Unfortunately there is no simple answer without doing your own homework. Italian rail is fairly cheap when compared to other countries. So you would have to use the pass at lot -- at least every other day -- to make it pay. But you will not know until you determine the point to point ticket price for each trip. My guess is that p2p will be cheaper.

I agree with Frank. You need to do a bit more planning. I will tell you that I have been doing cost comparisons between a railpass and P2P in Italy for a few years and the railpass is almost never less expensive. On most of the trips that you describe above, you will most likely be on high-speed Eurostar-class trains. Italy charges a reservation fee to Eurail pass holders of 15E-20E for riding on the Eurostar. You could be looking at an additional $90 just on the above travel. You need to add this to the cost of your railpass. Also, if you plan on visiting the Amalfi coast, the private railway from Naples to Sorrento does not accept the Eurail pass.

If you click on the Railpasses tab at the top of this page you will find tools to help you calculate point-to-point ticket costs and compare to railpass cost.

I'm thinking the pass is more expensive than point to point. What I do know for certain is that buying tickets at the stations using the kiosks could not be simpler. There are tickets windows as well where you can deal with a vendor, but lines can be long and the kiosks are a snap..English language, clear directions, credit card friendly. We spent a month in Italy buying tickets like this. Have fun, and safe travels.