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Pt 2 (San G, Siena, Orvieto) of 31 day Italy itinerary-can you help?

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Hello all,

I am posting this itinerary in several parts, hoping to get experts on the areas we'll be visiting.
To briefly summarize, I'll be traveling to Italy in 12 days (!) with DH and two teenage sons (14, 16), and I'm hoping that the experts out there can help me to refine our itinerary.

Here’s the overview of the whole trip:

Fly into Venice. Stay 4 nights
Train to Florence. Stay 5 nights
Drive to San Gimignano. Stay 2 nights
Drive to Siena. Stay 4 nights
Drive to Orvieto. Stay 1 night
Train to Rome. Stay 4 nights
Train to Naples, private driver to Positano. Stay 7 nights
Return to Rome. Stay 2 nights
Fly home from Rome

This post relates only to the San G, Siena, and Orvieto part of the trip.


Part 2: San Gimignano, Siena and Orvieto

Day 10: San Gimignano
We’ll pick up a rental car at Hertz in town (ug-last time it took about 2 hours—does anyone have a better suggestion on how to get the car?)
We’ll drive to San G, perhaps visiting Greve or some other small town first, to avoid the mob scene at San G. Plan to arrive at San G around 4:00, and spend a little time exploring the town. Possibly we will visit the museum if it is still open. We’ll be staying at La Cisterna in San G, where we have stayed before. We love the view from their outdoor balcony.
Dinner at Il Trovatore

Day 11: Get an early start, and take the museum tour if we didn’t get to it the day before. Go up to the fortress and possibly have a picnic lunch if it’s allowed. Then perhaps a cooking class? Other options might be a day trip to Lucca or Volterra. I’d be very interested in your thoughts on these days in San G and how we might best enjoy them.
Dinner at Cum Quibus

Day 12: Siena
This will be our base for driving around to some of the other small towns in Tuscany. After check-in at Palazzo Ravizza, we can explore Siena, go to the Campo, tour the Duomo and museum.
Dinner reservations at La Taverna di San Giuseppe, where we have eaten before, and it’s one of our favorites.

Day 13: Road trip! Towns I’d like to visit would be Pienza and Montepulciano, which we visited last trip and loved. It might be too much to try to get to San Antimo Abbey as well, but it would be nice to go when we’ll be so close. Any thoughts on this?
Dinner at Antica Osteria da Divo

Day 14: (Sunday) Knowing that many things will be closed on Sunday, I’m still looking for something to do that day. We could possibly visit the home and chapel of St. Catherine, but that won’t take very long.
We still don’t have a dinner reservation, but I’m working on it.

Day 15: Still open—I’d like to do another road trip. Any suggestions on favorite towns?
Dinner: Zest Ristorante

Day 16: Orvieto
We will get an early start and drive to Orvieto, where we will drop the car. We’ll only stay one night, but I’ve never been there and really wanted to get there this trip. We’d like to visit the Etruscan Museum, Duomo and possibly Civita di Bagnoreggio. Does anyone have any suggestions on how best to accomplish this?

Dinner: Duca di Orvieto

Day 17: train to Rome
I have not booked these tickets, because I’m still working out the Orvieto part of the day. Can anyone offer any suggestions on which train would be the best to get to Rome, and if I should pre-book, or just wait and do it there?

Thanks for reading thus far, and I truly appreciate your assistance, as the day of departure is quickly approaching!

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