I always recommend Certaldo as a great base to see Tuscan countryside and be very central for the main places people like to see.

Certaldo area is a great base as it is right in the middle of an area exactly half way between Florence and Siena in which there are some lovely places to see like Certaldo Alto, San Gimignano, Colle di Val d'Elsa, Volterra and Monteriggioni. The train station in Certaldo has a free large parking lot behind it so you can easily go to Florence (to the north) and Siena to the south) by train without having to worry about parking. For driving between towns the roads in this area are much more gently hilly and curvaceous than in the main Chianti area around Greve where the terrain is much more mountainous and steep.

There are loads of good, inexpensive places to eat local food and there are also many family-run wine producers in this area.