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3 days between Florence and Rome

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My friend and I will be travelling through Italy in October, we are two females from Canada who are fun and love great food and wine.
My family is from Northern Italy and I have visited before but this will be my friend’s first visit.
We will be leaving Florence by car Sunday Oct 21st and don’t need to be in Rome till Wed Oct 24th.
I initially thought of staying in a B&B outside of the old walls of Siena and using that as a base to tour around for3 days, stopping in Chianti, Montalcino, Pienza etc.
I’m now thinking if we are driving south to Montapulcino and eventually going to Rome, should we cut our stay in the B&B one night and stay near Montapulcino or somewhere similar and be on route for Rome.
Also, any suggestions as to artisanal cheese makers in the area, my friend is a cheese sommelier on the side and I would like to take a wine and cheese tour of some sort in the region.

Any suggestions appreciated, thanks

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