I will be staying in Gaiole in Chianti for the first week of May. I will be arriving into Rome on a Saturday morning and renting a car and driving to the villa. Since I cannot check in until 4pm and my flight arrives at 9am I am looking for suggestions of an interesting town or attraction (monastery, winery, vineyard etc) to stop and see between Rome and Gaiole in Chiante (15 miles from Siena). Also any suggestions for a good restaurant to have lunch at along this route is appreciated.

Thanks!

I would divert over to Montepulciano and have lunch at Cafe Poliziano.

If you do go to Cafe Poliziano and the weather is nice...walk all the way to the back of the cafe and you will find a small balcony where you may eat and enjoy the view.

Montepulciano is quite nice. I also really like Pienza very much. Especially if the weather is nice, try Latte di Luna, Via San Carlo 2. It's at the far end of town from where you first approach by car, but that of course that isn't very far.

You could stop at Montalcino (a great wine shop in the fortress) and also visit the nearby abbey of Sant'Antimo, in a very picturesque setting.

http://www.antimo.it/

She is driving on A-1 to Gaiole. I doubt if she wants to divert that far.

If you are driving on the A-1 from Rome to Gaiole, you might want to stop in Arezzo. It's not far off the A-1, and on the first Saturday of the month there is a large outdoor antique fair.
I'm curious, which villa are you staying at in Gaiole?

I will be driving on the A-1.

The villa I will be staying at is Villa Cavarchione. If you are familiar with it please let me know what you comments are.

Thanks!

No, sorry. We stayed at another villa. Still, I think you will love Gaiole. Have a great trip.

Orvieto. Very close to the A-1 and not far north of Rome...a great place to visit. The Duomo is a marvel. Park below the town and take the funiculare up to the top.

LowCounty,
How was your stay at Cavarchione? We are considering staying there as well. Curious as to your opinions of it.
Thanks!