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Where Would You Add Two Days - Tuscany & CT Itinerary

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Last year we experienced our first travels to Italy and spent 10 glorious nights between Venice and Rome (4 nights Venice, 6 nights Rome with a day stop in Florence). We are now planning our Tuscany and CT Escape for early June 2015. Wish we could make it in May, but our schedules won't allow it. I sketched out a rough itinerary and actually have 2 days to fill. Fodorites are so helpful in planning a perfect trip so I wanted to run this by you for feedback:

Day 1: Fly into Rome from DFW; train to Orvieto; overnight Orvieto
Day 2: Train or bus to Montepulciano (rent car)
Day 3-4: Montepulciano with a day drive through Montalcino, Sant Antimo, Pienza, Monticchello
Day 5: Drive to Siena via Asciano route
Day 6-7: Siena with a day drive through Chianti (return car)
Day 8: Train/Bus to Rioggomore (day stop in Florence using left luggage at station)
Day 9-11: Rioggomore
Day 10: Train to Pisa
Day 11: Fly out of Pisa to DFW

With the above, I have 2 days to add "somewhere". I am not a fan of one nighters ;) but with the airport situation, Pisa - I think - is unavoidable as I don't think I can get from CT to an airport the day of flight. If this is possible and/or advisable, please let me know.

I've always wanted to visit Orvieto so I figured we could spend our first day/night there when we arrive. I read about doing the left luggage at a hotel, but then figured by the time I did that and paid for our bags, we might as well just get a room for the night and head to Montepulciano the next morning.

My initial thought is to add a day to both Montepulciano and Siena or should I add another destination?

We prefer to spend our time "at" our destination not driving/traveling between destinations. Also, my husband would prefer to spend as little time as possible driving.

I know the day stop in Florence might appear odd but we did it last year and it worked out great so thought we could do it again since we will need to connect there anyway.

Thoughts?

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