I can't offer too much on the wine front as to buying strategies except to echo Craig Camp's comment that there will be no real deals due to the current exchange rates. I was there in September and the rate was 1.15 and I had a bit of sticker shock when I factored that in.
I ended up lugging about a case back, but of mostly sentimental wines more so that gotta have wines. The wine shops all generally have English speaking dudes, especially in towns of a larger size or where tourists are more likely to venture.
If you want tips on where to eat or what to see/not miss, particularly on the Firenze (aka Florence) bit, I can offer you some recent tips as I was just there. Let me know if you're interested and I can elaborate.
www.vinocellar.com -- Mm-Mm-good