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Tuscany in May- Pienza first week, second week ?

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We will be flying into Rome in mid May and staying for two weeks. With your help, we plan to take the train to Orvieto, stay one night and rent the car from there. I've booked a nice Agritourisimo in the Pienza area for a full week hoping to visit all the nice towns there and maybe venture up to Siena as well. We had taken a prior trip in 2000 and visited Rome, Florence and Venice.

The problem is I booked our flight out of Milan thinking we would end up in the lake region but Fordorites suggested otherwise. I'm thinking of three days in Lucca and three days in Bologna since I see there is a high speed (one hour) train from Bologna to Milan and enables us to make a 10:30am flight to the states. Should we stay more in the Chianti region or perhaps the Arezzo area? I've read that Lucca is lovely but the area surrounding it is industry and crowded. Not sure if it is a good idea, especially since near beaches Cinque Terre might not be ideal in May. Ug please help. :)

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