The Tuscany south of Florence is full of wonderful places like Montepulciano, Pienza, Siena etc. You need to look carefully at a tourbook to choose what you're interested about, i.e. art museums, churches, country towns, old ruins etc. I suggest you to take the highway and then exit at the pints of your interest, if you have little time and you don't want get lost in the countryside. On the way from Florence to Milan I suggest to stop in Bologna and/or Parma, two old but well preserved towns full of museums and vintage buildings. You'll find there great food too!

Have a nice trip

Paolo Trieste, Italy