Orvieto-Greve in Chianti-Asissi-Gubbio

I think the drive on S 222 (the Chianti Road) is beautiful. Depending on the days you travel, there will be different events and markets taking place. Montalcino is very cool, I think. Gubbio is quite different - very medieval in look and feel and worth the excursion. You're starting to get in way rural Italy in that direction.

Wineries are hit and miss. Larger commercial ones are open to the public. Smaller ones usually are not. But there are wine tasting rooms in many of the towns.

Mark, that is good to know, thanks! I was under the impression that wine tastings, at wineries, at least, had to be made in advance. So there are some you can just pop in? Shops have wine tastings, too?

We enjoyed this spot in Greve. They a great selection of wines as well as Tuscan olive oil.

http://www.lecantine.it/cantineUtente/index.php?cambialang=en

If you are in Greve, stop at Macelleria Falorni, a wonderful butcher shop in the center of town famous for its use of wild boar. It would be a great place to buy supplies for a picnic.
I don't have a map in front of me, so I do not know if it is too far for you, but I highly recommend a stop in Panzano. Charming town with a wonderful and famous butcher shop and restaurant. Again, now knowing distances, I would also recommend a stop for lunch at Trattoria Il Leccio in the tiny town of Sant’Angelo in Colle near Montalcino. Then after lunch stop at Sant’Antimo Abbey, a 12th century church and monastery to hear the gregorian chants.

Mark and Kristy:

First, I echo ekc's comments about the butcher in Greve and the village of Panzano. Panzano is a hill top village about 10km south from Greve on the S222.

Restaurants: Near Greve is one of our all-time favorites - Ristoro di Lamole in the tiny village of Lamole. Try the mid-afternoon Sunday supper. Wow. The restaurant has a website - be sure to make a reservation.

Wineries - we have been to dozens of spots in Chianti - here are our favorites:

1. Panzanello - small family run winery with nice wines and great people. Located just outside of Panzano.

2. Vignamaggio - located near Greve. This is the estate where Mona Lisa lived (I'm not kidding). This is also the setting for Kenneth Branagh's film of Shakespeare's Much Ado About Nothing. A beautiful estate and wonderful delicate wines. Their vinsanto is a poem.

3. Volpaia - this little hilltop village has been completely subsumed into the winemaking operations. Great wines.

All three places have English websites. As others have recommended - do not just drop in. Email or call ahead of time and make a reservation - it will enhance your wine experience. Plus, by arranging ahead you can set up a luncheon or dinner at each place as part of your tour.

Have fun.

I agree about Lamole, but in the interest of full disclosure it is located at the top of a large hill, along a winding road, so don't overdo the wine or the drive back down could get a little dicey... We also thoroughly enjoyed the tiny town of Castellina and had the best lunch at La Vigne restaurant, in the middle of a vineyard, right outside nearby Radda. Also, we were disappointed to find that the "Singing Butcher" of PBS fame closes his shop in Panzano on Wednesdays (the day we were there)--or at least that was the case 5 years ago. One last thing, if you can hit Greve during the Saturday morning market, it's quite an experience!

Its funny, I considered the 222 to be a one day pleasant drive to Siena. On the second time down the 222, it became apparent that it is a two day drive to really experience it. So we are going to over night next time at Castellina or at Greve. This road made us slower travelers. The wild boar sausage, cheese, local wines, little olive presses, and the general off the beaten path aspects of that area is a major part of wanting to return. So if you can make another day somehow in the schedule to explore this area, I'd do that.

Thanks to everyone for the EXCELLENT suggestions!! We really had a wide open schedule for the time frame we will be there (May 11-13th) so now we have some great ideas. Thanks again!