5 nights in Tuscany and/or Umbria

There are several places you can go for wine touring.
But you will need to rent a car definitely.
The 2 top wine areas would be Chianti,Montalcino, Montepulciano and Pienza.
We used the following web site to plan our trip.
http://www.bardotti.com/chianti1.htm
This web site tells you quite a bit about the region,
If you want to visit the wineries, you will have to make an appointment at most.
Montepulciano is famous for Nobile di Montepulciano and Montalcino for Brunello which is considered by some as the best wine from Italy.
Rudy Maxa's show had a tour of Banfi in Montalcino and this is the web site
http://www.castellobanfi.com/
The best place to stay would be around Siena in an agriturismo or farmhouse. That way you could drive north or south for wineries without driving too much. Most agriturismos will rent for a week usually Saturday check in and next Saturday check out.
Check out this web site for farm houses
http://www.agriturismo.com/toscana/en_index.shtm

We had a fabulous tour/lunch/winetasting experience at the Verrazzano Winery in Greve in Chianti. (Yes, the explorer's family!)