We are planning on driving from Florence to Orvieto then spending the night in Orvieto and taking the train to Rome.
Any suggestions on route and towns to visit? The purpose of renting the car is to see some countryside so we would prefer to stay off the big highways.

Is a stop in Siena too ambitious? Would we be better suited to stop more in the Montelcino/ Piensa area? Any gems for places to eat? Goal is leisurely drive with a nice lunch and poke around shops and such. Oh and we will be doing this on Oct. 9, in case that changes any suggestions i.e. fall festival.

If your goal is a leisurely drive, then don't get trapped by the Italian lunch hour.

Get a good guidebook, and it will readily show you the most scenic route through the areas south of Sience, le Crete Sinese (around Asciano), and then on to Buonconvento, Montalcino, Pienza, Montepulciano, etc.

Italian restaurants serve lunch between 12:30 and 2:00. By noon, you should have pulled off the road to find a place to eat (if you aren't in Siena -- then eat in Siena).

if you don't want to buy the Red Michelin guide for Italia, which will recommend to you wonderful restaurnats for even the tineist towns in that area, then pack with you lists of restaurants between Firenze and Orvieto along your itinerary, and mark them on a map so you can find them while you're traveling.

But I LOVE the red Michelin guide. It's allows for incredible freedom while traveling. It's in Italian, but it uses icons and pictographs, and it's easy to decipher.

Sorry for my wacky typo! I meant to type "Siena" (not "Sience")

Thanks zepppole.
Ideally, I would love to use the Michelin guide but we just don't have time to order and figure places to eat out since we fly out to Venice on Saturday (Oct. 3). We will have a map in all likelihood. What we are trying to avoid is the "we are starving and have no idea where to eat/where to stop" We can plan around towns. Along that general route, does anyone have suggestions?

If this is just one day enroute, I think Montalcino is too much out of the way. It will only take you a little over an hour to get to Siena from Florence, but might take equally long finding a parking place. From Siena to Pienza isn't much more than an hour. Montepulciano is between Pienza and Chiusi where you might want to take the autostrade the rest of the way to Orvieto.

Have you tried the viamichelin or mappy websites? You should be able to select scenic routes or non-autostrade.

Florence to Orvieto then you need to take S2 which is a far more interesting drive. Siena is doable IF you know where to park. IMHO the best towns are: Siena, Pienza and Montalcino. Email me at [email protected] and I can send you a spectacutlar restaurant list for the area.

What time are you picking up your car and leaving? That will tell us a lot.

Do you want to see Siena? If so, I would suggest taking a very early train to Siena, stow your luggage in the train station, tour the town, pick up your car before the noon closing and immediately drive to a lunch spot. Continue your tour, taking a scenic route through Montalcino, val d'Orcia, etc, for Orvieto.

If you are willing to forego Siena, pick up your car in Firenze and use Michelin or Mappy for a rough idea where you will be around noon. Most of these tourist-hilltowns have parking lots that will be empty in October -- unless it is market day or a "feste" day. Do some research.

PS: If you are starving, eat. You can go crazy trying to only eat in recommended restaurants. Of course it is sad when you don't hit the nail on the head, but Tuscany is filled with places to eat and put the priority on enjoying the drive, not making tracks to some restaurant recommended by tourists. Five of the best meals I had south of Siena were in Buonconvento and Lucignano -- two towns most tourists never set foot in. Go for the scenery. It's unique. Tuscan food -- at its best -- is not the greatest cuisine in Italy.

From Florence, I'd take S 222 towards Siena; it's called the Chianti Road and the views are amazing. Then I'd pick up S 2 south of Siena heading toward Montalcino. A little southwest of Montalcino is Fattoria dei Barbi where we had one of our best meals in our 4 trips to Italy; we still talk about it. Evocative setting, charming staff, and an interesting Brunello museum on the grounds. Reservations might be a good idea if you can judge the time.
http://www.fattoriadeibarbi.it/01_en-1-home.html

Or if it's more about the shops, take S 2 from Florence to San Gimignano. It won't disappoint on that score and the lunchtime meal we had there near the well was pleasant. And the gelato across the piazza is supposedly the best in Italy.

Or you can continue on S 2 to Monteriggioni, a neat walled medieval village with a couple of restaurants. Don't remember a lot of shops.

The plan is pick up the car around nine or ten in Florence on Friday morning. I am fine with skipping Siena. This is our first trip to Italy so everything is exciting and new. I will start looking at some of the towns mentioned here. Thanks so much for the Michelin and Mappy suggestions, those sites look very helpful.