Hill Towns of Tuscany, Which to Choose?
 

My wife and I will be staying in agroturismo in Monteroni d'Ariba for three nights from September 29 to October 2.

Prior to my arrival, we will have already visited Florence, Montereggioni and San Gimingano. We plan on spending a full day (most likely September 30) in Siena. But what do the following day??

We will have a car, so we have many options but can't decide: Chiante, Monutepulciano, Arezzo, Perugia, Cortona?

Any advice on which to visit or if there are other I may be neglecting?

While not in Tuscany, I'd highly recommend Assisi. Overnight visit would be best to see the town at its best.

We liked Cortona, very doable for a day trip, a little more mountainous then Montepulchiano and Cortona is right next to Umbria countryside, which gives you another perspective on the lay of the land. Gubbio and Assisi wonderful but may not be doable as a day trip.. That all said Montalcino, Pienza, Montepulchiano are all close to each other and give you typical gorgeous Tuscan views (those gorgeous Tuscan hilltowns tend to all run together!).
Chianti region is made up of many small towns., curvy, hilly roads... You could do more than one town if doing Chianti region.
Have fun!

Castellina in Chianti is lovely. But, I do also like the idea of Assisi.

You must like hotel changes. I would stay in Siena and day trip to Abbazia Oliveto Maggiore in the AM via Asciano, and Montalcino in the PM--best wine town in Italy.

You are an easy train ride from Monteroni D'arbia to Siena (15 minutes) if you don't want to take the car. Last return train is at 19:51 so if you plan to eat dinner in Siena, you would need to drive.

I would take one day and drive to Pienza for lunch and Montalcino for the rest of the day.

Having stayed in many agriturismo, I would recommend that you determine your other day trip when you get there. The owners of the agriturismo will have good advice for you. It my depend on several things that we can't know now: the weather, is there some festival or interesting market on, road diversions, etc.

Often you'll find out from the other travelers staying there what is good at that time. And it may depend on how you feel....if tired you may not feel like a huge drive that day. Or the grounds of the agriturismo might be so lovely that you decide to do a hike in the morning, and then go to a nearby hill town in the afternoon which would change the list.

All the places you have listed are wonderful. You can't go wrong in that part of Italy of course. Since the hill town you go to will not change your itinerary re: lodging reservations, then I would vote for deciding when you get there!

Happy travels,

LisaG

cdispoto,
This may give you some ideas http://www.slowtrav.com/italy/tuscany/hs_planning.htm