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Help planning day trips from Montepulciano w/ car

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Hello all!
My fiance and I are going on our honeymoon to Italy in a couple weeks. I have been reading up and trying to plan some good day trips from our hotel in Montepulciano since we will have a car the whole time there. We have never been to Europe/Italy, so we're excited to get out and see a lot. However, we also don't want to be in a car the entire trip.

Any advice on the second leg of our trip below would be greatly appreciated!

Leg 1: Venice (3 nights)

Leg 2: Montepulciano/Tuscany (4 nights)
-Day Trip #1: drive to Volterra, spend 3-4 hours, drive to Sienna, spend 5 hours, drive back to hotel in Montepulciano
-Day Trip #2: drive to St. Antimòs Abbey to watch Gregorian Chants at 9AM, stop in Montalcino, San Quirico d'Orcia, and Pienza on the way back to Montepulciano
-Day Trip #3: drive to Assisi, spend 4-6 hours, drive to Cortona, spend 2-3 hours, drive back to Montepulciano.
-Day Trip #4: drive to Civita di Bagnoregio early in the morning, spend 2 hours, drive to Orvieto, spend 2 hours. Catch train to Rome at 12:00p

Leg 3: Rome (4 nights)

Some of my questions of the bat:
1. Is this too much driving?
2. If yes above, what should we cut? (Is Volterra/Assisi/Orvieto worth it)
3. Any other advice based on what you see?

Map of our honeymoon including these day trips:
https://www.google.com/maps/ms?msid=211969406731211674214.0004c72525ad39b00ac09&msa=0

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