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Help wih planned day trips in Tuscany

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We have 6 full days in Il Borro, 50km south Florence, these were my planned day trips but need experienced advice.
These are suggested days but if we see something along the way where we would rather stop we will. We are early risers and this trip is to see more of the countryside and a good wander around most of these towns.(not necessarily every church and/or museum)

2 Cortona - Lago di trasimeno
3 Montacino - Montepulciano - Orvieto
4 San Gimignano - Sienna
Could we fit Pisa in with day 4?
According to Mappy the round trip for the longest drive is Orvieto and that is 4hrs 30min
After our week to drive to Genova, for Cinque Terre before train to Rome

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