Chianti would be a great base
Ciao lost,
Chianti would be a great base considering you'll have a car to move around and want to visit both Florence and Siena. Since you're staying just 4 nights, it might be hard to go with the traditional apartment in a farmhouse so I recommend looking for a small hotel, b&b or a farmhouse set up as a b&b with rooms by the night. Whether you stay directly in the center of a small village or just outside, you'll have various choices of where to dine in the immediate area. Always ask your hosts for their recommendations, as they are the ones that can point you in the right direction.
For very basic but central lodgings, you could stay in the
Verrazzano apartment in the main square of
Greve in Chianti, the heart of the Chianti wine region. Parking is available just a few blocks away, the town has many dining choices.
I also recommend
Palazzo Malaspina, a charming B&B right in the center of the small medieval village of San Donato in Poggio. Very elegant rooms. Here is a
list of restaurants in the immediate area.
If you're interested in treating yourself to very nice lodgings, I recommend
Villa il Poggiale, an elegant hotel set in a Renaissance villa just outside of San Casciano. Being in the countryside, it has the space for a great outdoor garden with views, pool and even a small spa for its guests. I believe they offer dinner for guests if requested and there are many .
All of these are in Chianti, the last two are closer to the Firenze-Siena road to make your drive into Florence and Siena even quicker, although the Chiantigiana road from Greve into either Florence and Siena is slower going but more scenic.
Let me know if you have any other doubts or questions that I can help with. Hope you're enjoying planning your trip!
