Buongiorno,
From Pratovecchio to Arezzo, it will take less than 40 min. And Cortona is just another 30 minutes beyond Arezzo. So these are two places you can visit even while you are staying in Pratovecchio.
One or two days in Umbria (I suggest that you do this before heading over to Montepulciano and Siena)
Montepulciano (Chiusi, Cetona, Pienza) is a great day trip
Montalcino (Buonconvento, San Quirico, Bagno Vignoni) is another great road trip
Siena is a great day trip - and if you choose to stay here you can make Montalcino & area a day trip from this base.
Ideas for Siena:
https://www.discovertuscany.com/siena/
Day trips from Siena:
https://www.discovertuscany.com/sien...rom-siena.html
I also suggest that you visit Bologna via train from Florence.
Buon Viaggio,
Donna Denise
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