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Tuscany and CT Itinerary Question

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I am planning our 2nd trip to Italy for next early June. We will have 12 full nights. Our first trip we visited Rome, Florence, and Venice. This time we would like to spend some time in the hill towns of Tuscany then end our stay in the Cinque Terre area. We plan to rent a car for the Tuscany portion of our trip.

I was thinking of flying into Rome then taking a train to overnight in Orvieto. The next day we could rent a car and head to Tuscany.

I am trying to decide if we should pick just one base in Tuscany or two since we will have 6 or 7 nights. The areas we would like to visit include Siena and the Val d'Orcia area. We would like to take a couple day trips to visit some of the abbeys and other towns. My first thought was to stay in the Siena area and just do day trips but since I would probably want to spend at least 2 days in the southern area I was wondering if it would be better to stay in Pienza or Montepulcino for 3 nights then head up to Siena for 3 nights. I prefer to lodge within walking distance of a town so we can walk in the evenings to dinner, etc.

After Tuscany, we would head to the CT area. I was thinking we could take the scenic drive through Chianti and have lunch. Then either drop the car in (Pisa or Florence?) and train to CT or should we just drive all the way to the CT area and drop the car there?

I want at least 4 nights in CT because in addition to the area itself, we want to take a day trip to the Portofino/SML area and also Portovenere. I haven't decided if I want to base in CT or maybe the SML area ... so many pros and cons of both options. Either way, we would take a train to fly out of Pisa at the end of our trip.

I actually have 1 extra night that I haven't accounted for yet so that would leave me with 7 nights in Tuscany of 5 nights in the CT area.

I would appreciate any feedback or advice from the experts. Thank you!!

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