Rail Pass?

rarely are railpasses economical...

you can buy economy and super economy tickets well in advance of your travel dates and save a SUBSTANTIAL amount of money.... www.trenitalia.com

Weather or not a rail pass will benefit you will depend on the locations you are traveling to and the number of days you'll be taking train trips. Sometimes railpasses are a good way to save money, and other times you end up spending more.

reviewing the detailed information at these links should help:

http://www.ricksteves.com/travel-tips/transportation/trains/italy-rail-passes
http://www.ricksteves.com/travel-tips/transportation/trains/should-i-get-a-rail-pass

I haven't used a railpass in Italy for over 20 years. If you can commit to a specific train departure time, you can save lots of money by buying up to 120 days in advance, but no changes or refunds are available for the super-economy fares.

It's not worth it unless you plan on being on a train every day. Since it is likely that you will stay put in each big city (e.g. Florence, Venice, Rome) for 2 to 4 days at the time without using trains at all, and since distances in Italy are short, you are almost certainly better off with point to point tickets. Also local train travel on Regionale trains (e.g. Florence to Pisa, or Rome to Orvieto) is super cheap.

I have priced it out a million different ways and did not find Italy prices worthy of a rail pass. Italy has some terrific super saver rates. I decided to book early since they were selling out and I love a bargain. They also have a 2X1 on weekends deal that is a killer deal.

The value comparison is not a matter of whether you'll use a train every day (since the pass allows you to spread travel days over a month), but of how far you'll travel on each pre-paid pass day. You need some long trips before a pass saves money over walk-up ticket prices. Advance-discount ticket prices can be even better, if you're committed to travel dates and times for a couple of rides between the bigger cities. Regional, unreserved train tickets should not be purchased in advance, since that makes them unnecessarily restrictive.

One other point to keep in mind is that Rail passes do NOT include the seat reservation fees, which are compulsory on the "fast" trains such as the Freccia high speed. You'll have to pay separately out-of-pocket for those (about €10 PP for the Freccia). Those who don't have a valid reservation for the train they're riding on (even with a Rail Pass) will be subject to hefty fines starting at about €50 PP, which will be collected on the spot!

As the others have mentioned, Rail passes are rarely the most cost effective option for travel in Italy.