Le Cetinelle, a small B and B just outside Greve. Simonetta and Luca are great. She speaks English. They have an self catering apt for 4 along with rooms. Beautiful Chianti side. Easy trip into Florence by car or bus.
They have a cooking class and then you can eat the dinner that night with Simonetta and her cooking friend Kalinka. (She is a great cook, speaks English and her husband runs one of the best restaurants in the area, Lamole. You need to eat there.)
Best I can come up with for all your "boxes". You will enjoy it.