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Recommendation for one day trip from Cortona for first timers

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I am planning a trip to Italy for my 50th this year and my sister and brother-in-law are joining and they have never been to Europe. They are spending time in Florence and Rome seeing the sights but are joining us for three nights in Cortona. I've been to Cortona and Tuscany several times and covered most of the day trips.

Since it has been a long time since our "first Italy trip", I'm curious on Fodorites' opinion on the "best" one day trip (and why) to take the newbies on which is only an hour or so away. We're only doing one day trip so they have a day to settle and explore Cortona upon arrival. My short list is as follows (they're more architecture/wander/shop types than museum types).

Montalcino, Montepulciano, Siena, Arezzo and Perugia

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