Thanks for all of the links, I will check them out. It will only be my wife and I on the trip, no kids. We are trying to have a good blend of sightseeing and relaxation (beaches, etc). We definetly don't want to have to take another vacation to relax from this vacation. :) As for flights, I've been checking out Expedia and Travelocity to get baseline prices, although prices are roughly ~$900 give or take 50$ depending on the dates. I briefly looked at priceline yesterday but I was unsuccessful in getting the destination airport to be in Italy, but I didn't spend more than a minute or two looking at it. Also, I think we would have no problem staying at condos, villas and alike, this is a good start let me know if anything else comes to mind. I'll update on things that I find.