Family accommodation in Florence center or surroundings
Dear Roberto,
I can understand your doubts. I'd like you think about the following:
if you are staying in
Florence city center, you won't have any extra-driving but you'll have to pay parking. As we mentioned in this article about
parking lots in Florence,
parking is quite expensive. Of course most of hotels have special agreements with private car parking, but still prices are about 20-30 Euro per day.
If you are staying in
Florence surroundings you don't need to worry about parking and extra costs. You can stay in a farmhouse or B&B in Florence surroundings, connected to Florence center by bus. For example Agricola Poderino that I've already suggested, or the nice
B&B La Paggeria, that is located 20 minutes by bus from the city center.
Regarding a day out in the Chianti region, I have a restaurant to recommend. Just yesterday I spent the whole day in Chianti with my family. We went to Radda, Gaiole and Castellina. We had lunch in
San Gusmè, that is an enchanting medieval village 10 km from Gaiole. In the small city center there is a nice restaurant called
Sira e Remino specialized in typical Tuscan food. It's delicious and I suggest you try
Pici cacio e pepe (pasta with cheese and black pepper) and
Tagliata con porcini (Florentine steak with porcini mushrooms). Gnammy, gnammy

and it's not expensive (about 25-30 euro per person). If you want to do some
wine tastings in Chianti you can read this article. You can find lots of wineries, farms and wine shops offering wine tastings all over Chianti, as well as in the towns you intend to visit.
On June 24th the final match of the
Calcio Storico Fiorentino generally takes place. I say generally, because for this year we have no information at the moment if there will be a match for sure. In fact, due to political-administrative issues there is no confirmation on whether the semi-final and final matches will be played. I suggest you wait and ask for information once you arrive and buy tickets directly on match day, if the game turns out to be played.
I hope my suggestions will help resolve your doubts and in making your final decision

I also hope you'll share your experience in Tuscany with us when you'll be back home.