The other thing I forgot to mention was the train website. Don't feel limited to using the trenitalia website only for bookings. Searches can be done on all the major train websites, bahn.de or SNCF website. Just gives a few options if language becomes a problem.
Also they open up availability 90 days in advance.
Not sure if all the others have all the fare types though.
As of Jan 22, 2011 Trenitalia has introduced a new fare system. Also at about the same time the booking hassles with non-Italian CC seem to have disappeared.
If you can get the "Mini" advance fares they are a bargain. ie Some fares may be reduced from 65 to 7 Euro!!! Minis are supply and demand though..tey start uoff very cheap and as they go the Mini fares rises. So book as soon as you can when Minis appear.
I have just booked for an April trip and gained Mini fares on all legs. Maximum was only 17 Euro..and minimum 7 Euro...for 3 hour trips on their fasst and best trains . It is travel bargan.
I am in and out of Milan.
So have booked:
Milan to Venice
Venice to Florence
Florence to Rome
Rome to Pisa
Pisa to Monterosso (Cinque Terre)
Monterosso to Milan
The website I found very easy to use. The bookings page is all in English if you click on the English icon.
One requirement though is that you need to know the Italian name for the station. ie Milano Centrale etc
The other good thing about getting the Mini fares is that you have pre-booked seats...so no need to queue up again. to geta "reservation" like you would if you havea Eurail Pass.
drawback is that I have had tp pick fixed days...but as I am only there 2.5 weeks that is nota disadvatage to me.
Hotel wise...a bit of searching Hotel Booking engines and cross refererencing with trip Advisor has produced some good econmical options all following my main mantra of LOCTION, LOCATION, LOCATION.
We will be able to walk everywhere to most of the key sights and most likely will not need one taxi fare.
In Roma we have an appartment for 5 nights about 250m from the Colosseum..and near the metro..two steps from the main train station that we arrive and depart Roma from..so might even just walk to get there.