Joinable or private (wine) tours from Florence to ...


Hi i have 2 questions about tours.
I was looking for some new kind of tours to do from Florence to .. some interesting cities or wineries.
I visited Pisa, Siena,.. already
San Gimignano would look nice but can't find any tour without Siena or Pisa.

Also i'm a big wine fan and would love to visit the places like Montalcino or Montelpuciano, or some others, Chianti i see a lot over the past years so something other than that please.
I found some but they are for minimum 2 or 4 persons and costed around 300-400 euro and that was just a little but more than i wanted to give.

I don't know if there excist something like little or joinable tours or tourguides who just started and needed to practice or so..