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Train/Car options for Rome-Tuscany-Dolomites trip

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Hello.
We are trying to figure out the best options for Car Rental/Train for our Rome-Tuscany-Dolomites trip in January. I’m having trouble deciding on pickup/drop locations which work for our trip. I can’t decide between:
• picking up the car in Rome (city or airport) or in Tuscany (Chiusi or Orvieto)
• dropping of the car in (Chiusi or Orvieto or Florence) for the onward train journey to Bolzano

We have the following accommodation bookings and so I’m looking for advice for the 2 travel dates of 5th and 9th January that would work best with our accommodation and destination locations.
• Rome (Palazzo Olivia) – 6 nights departing Tuesday 5th Jan
• Montepulciano (Sant' Antonio) - 4 nights arriving 5th Jan and departing Saturday 9th Jan
• Ortisei – 7 nights arriving Saturday 9th Jan

We are from Australia and have driven in Italy before as part of a 6 week multi-country trip during October/November a few years back. It included every sort of weather condition including snow/fog/torrential rain. We have driven into and out of Florence city centre which was very scary but we survived - so we could do that again if required. We usually book in advance through autoeurope.com and have had nothing but good experiences with them so far.

I’ve been trawling this forum for ideas but just thought I would ask you all what might work best for us since we don’t need to go to into Florence this trip.

All your advice gratefully received.

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