If I were in that area, my fantasy would take me to Arnolfo, a MIchelin ** that has been fondly written about on this board in the past.
There is also a Michelin * place in the Certaldo old town that you might look into in addition to all the other alternatives in San Gimignano, etc
Hope you report back on your expereinces on this trip!.
re: jen kalb
Now with so much collective experiences from all you Chowhounders surely there are others who have some ideas, perhaps if we broaden our search to the Chanti area too? We are not necessarily looking for Michelin rated, blow the bank, but great food in wonderful surroundings that will culminate a great two week family trip with only four of us left after the rest of our family go home.
We have a car so off the beaten track is fine.