One week or two?

That is too many places to go to in one week. Why Milan? Every time you travel from one place to another you incur costs and use up valuable time. Plan to fly into one city and home from another, such as fly into Venice and out of Rome. How much time to spend in each place is a matter of deciding what you want to see the most. I wouldn't bother staying in Pisa. It would be an easy day trip from Florence.

You might want to spend the two week break in Italy. Use your other week for another place. My son spent a semester in the UK. He traveled to Paris, Switzerland for skiing, Dublin and, of course, Amsterdam. Some of these places can be done in a long week-end. Have you looked into hostels to save money?
If you haven't already, get youself a copy of Rick's Europe through the Back Door - lots of good advice. How exciting! My son loved his time in Europe. He also met all his academic responsibilities (lol!)

Hi Melissa. I also recommend 2 weeks for the number of cities you want to visit. As for how long to spend in each city, as another poster said, make a list of everything you want to see in each place. Verona can be done as a daytrip from Venice and Pisa as a daytrip from Florence. I would recommend at least 3 days in Florence (plus a fourth day for Pisa) and at least 5 in Rome. As for money, bring an ATM card for cash and a credit card for bigger purchases. I like to bring some local currency with me so that I do not have to immediately look for an ATM. Will you have a local bank account in the UK? If so, you can get 50 or 100 euros at your bank to start you off in Italy.

I agree to spending the 2 week break in Italy and the shorter break somewhere closer. Also agree to skipping Milan, unless the "Last Supper" is really important to you. Better to spend more time in fewer places and get to know them more thoroughly. Trust that you will return. As for Pisa, I was just there as part of an afternoon trip from Lucca. Too many people, too many tacky souvenir stands and people hounding you to buy there junk. It was my least favorite part of my 3 week trip. Not worth putting into a 2 week time frame. Allow at least 3 days in Venice and Rome. Verona can be done as a stopover during the day on the train from Venice to Florence. Not worth spending the night.
Enjoy your time!

I also concur on 2 weeks -- much better. I'd add Siena to your list. Much more to do and see there than Pisa, for example. Milan is very industrial -- not really a tourist city. I occasionally get to go there for work, so don't bother with it when I'm on vacation. Not worth it, IMHO. Take some cash (200 Euros or so) for those places that are cash-only & emergencies. Credit cards are much better & safter for most purchases. Pick one that doesn't charge any foreign fees (e.g. Capital One). That way you don't have to guess how much money to change. Mathew

Have you followed the Andy Steves links off the RS website? Andy, Rick's now just about all growed up boy, specializes in just such, for folk just like you.

Melissa, If you are looking to stay within a budget, I would recommend staying in hostels. It's also a good way to meet other people. I would recommend The Beehive in Rome and Hostel Archi Rossi in Florence. Both were a great deal, clean, safe, and in good locations.