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Tuscany

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I am planning a last minute trip to Italy in mid May. There are four adults and we will be flying into FLR from the east coast. My original plan was to rent a car upon arrival and travel to an Agriturismo in the area of Siena. Thoughts were to stay there for five nights then return to Florence for three nights.Towns that we had thought might be fun day trips are: Pienza, Montepulciano, etc.
Found a great Agriturismo outside of San Gimignano.
The other couple would like to go to Cique Terra. I realize weather is always a factor.
Please advise me as to whether this would be too much travel in a short time or can we make it work without too much hassle.
Many Thanks!!

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