If you are still considering round trip, mobissimo.com is my new favorite flight search engine. Very comprehensive, but I don't think you can search for open-jaws there. Otherwise, would suggest you try the airline sights directly...e.g. alitalia.com...as I have had some trouble recently with flights not showing up on the search engines. Our direct NYC-Athens flight on Delta, for example, only showed up on delta.com - - - but not on expedia. Not sure why.

Are your travel dates flexible? Mid-week fares (T, W, Th) are often a bit less. Just as a test, I tried BOS-MXP on W 7/6 & FCO-BOS on W 7/20 and got a $950 fare on cheaptickets.com. NAP-BOS was just a few $$ more (roughly $50 I think).

Try playing with your departure/return dates, and check the various websites at different times of the day and night.

Good luck.

Hey Matt, I'm a fellow college student. Went to Italy when I was 20, my first time to Europe too. Good choice!

As far as 4 days in Tuscany, 3 days in Florence and 1 day in Siena would be perfect. Cortona is beautiful but Siena is going to be much more interesting of a place. It's also closer to Florence. Arezzo isn't all that interesting.

The nightlife in Florence is decent. It's better in Rome, and nonexistant in the smaller Tuscan towns (ie Siena or Cortona). You won't find it either in Amalfi, although Naples will have some.

As far as the flight, you'll have to be patient and keep checking the websites. Eventually you should find something under $1000. Hotfares.com is pretty good, I usually use it and travelocity.

Rar,
Thanks very much, I have been dying to get the input of a peer who has been in the same position! I'd love to hear about any of your other experiences, particularly Rome. Any and everything we can learn is very valuable to us!