Recommendation for one day trip from Cortona for first timers
 

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

for the average person Siena and it would fulfill their wish lists - if they are into Saint Francis of Assisi then Assisi is a nice but more modern hill town with lots of sites associated with Frncis as well as Claire (sp?) of Assisi.

Perugia is a large hill town whose sizes masculates its hill town appearance.

Have not been to Montalcino but Montepulciano to me was too small to spend more than a few hours in - an iconic small hill town - I'd vote for Siena.

I suggest Assisi. Cortona is on the border with Umbria so you have easy access to towns there.
From your list, both Montalcino and Montepulciano. We visited both as a day trip from Cortona
along with Pienza.

I would consider this experience--not far from Cortona.

http://www.avignonesi.it/en/hospitality

Thanks all. I think we'll go with Siena as the campo and striped Duomo are pretty amazing since it's their first trip. Loved the others ourselves but as a starting point Siena seems like the right size. Bob - thanks for the link and we'll check it out on one of our days without my sister as that looks right up my alley (my sister isn't big into cooking or wine).