We've decided on Italy and are now trying to plan out our trip. Figuring out how to fit everything in is going to be somewhat difficult, as we would like to spend a couple of days each in Rome, Florence, and Venice, and also check out Milan and Genoa if possible. We are also going to try to avoid the high tourist season, but we don't necessarily want to be covered in snow if we go to Milan. Finally, we do want to have a little flexibility in the schedule so that we can stay an extra day or 2 in one of the cities if we decide there is just too much we have to see before moving on to the next one.
To start preparing for the trip, we went to Barnes & Noble last night and purchased a couple of Italy travel guides (Frommer's and Fodor's). While they are very similar, they do have some complimentary tips in each, and having both allows us to read them independently. So far, it looks like our biggest problem (other than the logistics in general) is going to be looking out for pick-pockets (both books warn against it). We can probably deal with this problem without too much of a problem, but it is definitely something we need to keep in mind.
Language wise, since Italian is a Romantic language, both AM and I are able to recognize some of it (spoken and written). I'm able to pronounce a lot of it better than she is (she can't roll her R's), but she has a better memory. To try and get better at the language before we go, AM is going to go get some books on tape/CD on Monday. Hopefully we can get to the point where we won't get ourselves killed by saying the Pope is Mussolini's best friend.
Customs will also be a challenge. I will apparently need to register all of our electronic goods with Customs before we leave. Not doing so could open us up to having to pay duties when we come back to the US. Clothing is a bigger problem, as it doesn't have serial numbers. We will need to make sure that for any foreign made clothes we take with us we have a receipt to go with it.