Also going to Italy in May 08, and I booked my flights two weeks ago. I always do plane first, then hotels.

Ok, so flight first. We are in Florida so it would be out of MIA, FLL, PBI on 5/7/08. For destination I would prefer VCE. But would fly into FCO or NAP if cheaper. Then home from either VCE, NAP or FCO on 5/19/08. We are going to Venice, Florence, Rome then Naples or the other way around. I have been checking flights and they all seem really expensive. Anyone ever fly TAP Air Portugal? I have really cheap fare from PBI to EWR. Then a good fare from EWR to LIS to VCE. Please assist. Thanks.

Always flights first..you can find low prices in hotels even last minute, but that doesn't happen on flights..at least in my experience here in Spain.

try kayak.com

I just booked our apartments in Venice and Tuscany--thanks to two Fodorite recs, thanks Franco and Patrick!--for the end of May/beginning of June 2008. Now I'll monitor the direct flights I prefer from JFK and will book either FF or $ depending on how quickly they fill up. If we were to stay in hotels I might book the airline tix first. Best of luck to you.

We booked a cruise from Venice (Fixed time sailing) and then used our FF miles to get there on a partner to CO. It was ok because our backup was to use the cruise selection airline if it did not work. We booked in Jan for a late May sailing. But normally,I would book an airline if using miles first since they are normally restrictive and then the accommodations. If I were paying up front, though, I would book A/L after the accommodaions.