Eurail Pass, Is it worth it??

Megan, You may find it very helpful to read the "Railpasses" section of this website (click the tab at the top of this page). You could also download the free PDF Railguide (look in the lower right corner of the Railpasses section for the download link. That should explain the difference between a Railpass and tickets. One important point to note is that Railpasses DO NOT include the reservation fees which are compulsory on the "premium" trains. You'll have to pay separately for those. DON'T be caught without a valid reservation in Italy, as you may be fined on the spot! If you buy P-P tickets, reservations are included. You could also have a look at the excellent Ron In Rome website for everything you'll need to know on travelling by train in Italy. Railpasses are often not a cost effective method for travel in Italy, as tickets are relatively cheap (especially if you can pre-purchase and obtain the "Super Economy" fares on the premium trains). In most cases, travel by train will be the best and quickest travel method for the places you mentioned. You may find it very helpful to have a look at THIS Short Video covering the trip from Rome to Pompeii. Although it's a bit "dated", THIS Video also has some good information. Buon Viaggio!

How do you preorder or reserve tickets for the train, especially in Italy? And, is point to point tickets different from a Eurail pass? Is the point to point ticket the one you buy there at the station?

www.seat61.com is the source of all knowledge for trains.
If you are searching the Internet for advice on European train passes, you should know that the French rail system has changed its involvement with some of the European schemes so be careful about out-of-date posts.

Megan, a Eurail pass is sold by a ticket broker. In Italy, the only free train you can ride is the basic Regionale train. All others require a supplemental fee that will include the seat reservations which you must have. You can buy any ticket on any train in Italy at the train station. No supplemental fees. Seat reservations on the intercity and high-speed trains are included in the fare. Eurail passes are not sold in any Italian train station. If you want to do some homework, you can go on to www.trenitalia.com 119 days out from your travel date and buy tickets on the fast-trains in advance for really great fares. The fares are fare less expensive than the cost of any pass you can buy. But, in trade for these great fares, you will be locking yourself into a specific travel date and travel time. Plus, the tickets are non-refundable. And, for the Super Economy tickets, they are non-exchangable as well. You will most likely be on very high-speed trains between Venice, Florence, Rome and Naples. If all of this is too intimidating, just walk up to the ticket machine or ticket agent at the train station about 2-3 days before travel and buy your tickets. You will pay full fare at that time as the economy tickets will most likely be gone. Also, you will lock yourself into specific trains and travel times with those tickets as well but 2-3 days is different from 119 days.

I have long since given up looking at the replies to this regular question, so if not mentioned yet start by reading at the bold print here - http://www.seat61.com/Railpass-and-Eurail-pass-guide.htm#Should

If the rail rates are like they were back in 2011, the Eurail pass is not a deal in Italy. Rail rates were incredibly cheap, even on the high speed lines. Do get a train schedule if possible and if your scheduling is known and tight, buy your outgoing ticket as you arrive. Go 2nd class as 1st class is just you and Italian Rail employees.

Per Thom's thoughts above, most of Megan's trains are very fast high-speeds. For Venice/Florence the fare is 45E (discounted 9E), Florence/Rome is 43E (discounted 19E), Rome/Naples is 45E (discounted 9E). The Regionale trains that she will be riding to Tuscany and Pompei are dirt cheap. Also, the Eurail pass does not cover the Circumvesuviana train to Pompei. It's only about 2E anyway. On top of the fares, Italy charges a 10Euro supplemental fee for each high-speed train that she will be on. The supplemental fee includes the seat reservations. That's another 50E-60E on top of the cost of the pass.

Thank you everyone! All of you have been very helpful. I couldn't have done this without your advice.