Buongiorno,
Your first day probably be (travel wise San Gimignano comes first)
La Spezia > San Gimignano > Greve Chianti (quaint and on the way - Montefioralle) > Siena (Day 1)
As for your second day:
Siena > Montepulciano (go to the furtherst town first and then head back in) > Pienza > Bagno Vignoni > Siena
Buon Viaggio
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