If you decide to visit Tuscany side, choise one is to have driver and he will take about your tour. Other wise if you rent the car and you are on your own take the map and enjoy.

From Firenze you can drive to Greve in Chianti. it takes you about 30 minute drive.

You are driving to the heart of Chianti Classico. Here is web site from Consortium of Chianti Classico 

If you like cheese you can stop at Podere Le Fornaci ( Via Citille 74, 50022 Greve in Chianti Tel. 328 4641586 ) Marco will do for you an excellent tasting of organic goat cheese. It is very spontaneous and not touristic place.

Wine maker to visit at Greve it is Villa Calcinaia

After that you can stop at Greve and see this small neach village. 

Next after you drive to Panzano in Chianti, you can see signs ther are very well marked. 

Vinery you can visit Le Fonti family vinery with great price quality wines. I love their style and way they are thinking.

Next worth vinery to visit is Fontodi i was always fun of this wine maker. Realty with clear ideas and commercialy very organized.

If you like pasta, visit this wine maker Renzo Marinai which one beside great Chianti Classico can do even pasta tasting for you. They are directly producers of pasta and they coltivate on they own grain.

If you have time you can drive to Gaiole in Chianti you can visit San Giusto a Rentennano another great Chianti Classico wine maker, Castello di Ama with his own style.. There is many places you can go and visit, important thing is that you will never be disapointed.

Montalcino some of mysugestions:

Many others obvious