October is the best time of the year to visit Italy. The weather is cooler (low 70s), tourist crowds are way down except in Rome, the vineyards are turning golden yellow, and prices are off-season. Very cheap deals at elegant places to stay. Just try to stay out of the hospitals because that is no picnic.
Best thing of all: it is truffle season. Every decent place to eat had at least one truffle item on the menu, and we brought home two truffle pecorinos for Thanksgiving. Our lovely place outside Montepulciano (Villa Poggiano) put up a chalk board of things they would arrange for you to do each day. One of them was truffle-hunting. (Among others were a cooking class, horseback riding along the back dirt roads, and a rental Ferrari for 4 hours).
I declined the truffle hunt because you have to pay but of course you don't get to keep the black truffles. Also, I do not trust myself with a Ferrari although I do enjoy driving around rural Tuscany (in daylight only). We did happen to see a truffle hunter with his dogs on one of our own back-country hikes on which we got happily lost. I always have a half-roll of toilet paper in the bottom of my Osprey daypack. Who does not?
An American honeymooning couple at our place did everything on the list during their stay. Ah, youth.
As we drove around southern Tuscany looking at various hill towns and things (MapQuest got us everywhere), we stopped by a Roman bath, Bagno Vignoni. We had a nice light lunch there, pecorino ravioli with black truffle. Roasted root veggies on the side. That's Italian! I doubt that you have ever seen so many truffle slices in the USA. Naturally, I had a glass of Vino Nobile de Montepulciano. Fine for the purpose and helpful for driving confidence.
A few more pics, and a truffle hunting vid below the fold -