If you are into nice clothes, start saving your money now because you can get awesome stuff for dirt cheap over there.  Visit Naples and Rome for sure, and as long as you hit those you can't really go wrong anywhere else.  If you have 3 months to work with I would head north for a while too, bring those skis into a few different countries.  I have 6 countries under my belt for skiing, and like 20 something total just because they are all so close together.  Oh ya, if you go to a nice restaurant, go at  9 and plan on being there a long time.  They like to serve 4 or 5 amazing courses and take their time, and most people eat late.