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Italy in May - Tuscany suggestions

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My husband and I have been planning our trip to Italy from May 5 - 22 and are now narrowing down an itinerary (fly into Naples on the 5th and then staying at an agriturismo to see the AC. Naples to Rome on the 9th. Leave Rome by train on the 14th to perhaps Orvieto to rent a car. Then staying somewhere in Tuscany from the 14th - 20th and taking the train up to Geneva to catch our flight back.

We are trying to decide on a location to act as a base for our time in Tuscany. We have read quite a bit about the beauty of Southern Tuscany and so have been considering staying somewhere in the area of Montalcino, Montepulciano, Pienza etc. We drove quite a bit in rural France on a previous trip so while we have taken a few wrong turns, we are not afraid of driving. San quirco d'orcia looks interesting (the Palazzo del Capitano maybe? perhaps osteria dell'Orcia which I know is in Castiglione D'Orcia) or but was concerned that there might not be enough places to eat or stroll in the evenings (versus say Montalcino which I have read has quite a few good restaurants). Any input would be much appreciated.

We are, against much of the advice I have read on this forum, considering doing Florence as a day trip (perhaps via train from Siena or Buonoconvento). We know that it will be a very long day of travel but we wouldn't mind at least seeing the city and are really focused on having a relaxing 5 day stint in Tuscany and really don't want to move to Florence for a few days. So...if anyone had a suggestion for lodging that was, for example, closer to Siena, we would be open to it.

Thanks again in advance for your time and ideas.

Caitie

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