We are spending a few nights in Cortona and love touring small hill towns. We are trying to take in alot, but don't want to be too rushed. Our tentative itinerary while in Cortona is as follows:<BR><BR>Day One: Arezzo / Cortona<BR>Day Two: Montepulciano, Montalcino and Pienza<BR>Day Three. Perugia, Deruta, Todi, Orvieto or Gubbio<BR><BR>Any thoughts on whether Day One and Two can be reasonably accomplished? Also, any recommendations on which villages on Day Three should not be missed as can't see all of those on the list.<BR><BR>Appreciate your help.<BR>

Tom, Cortona is not the best location for all of those villages. It will be tough to make it to Montalcino, and I would drop off the south part of Umbria in favor of Assisi and Spello. Take the route around the Lake to get to Montepulciano and Pienza. That is a full day. Cortona is a great village but not well located. But, you will have a great time wherever you end up.

We had planned to see Montepulciano and Montalcino and Pienza in one day, but found that the day was gone after the first two. We just drove right on through Pienza.

Wow, day 3 - 5 towns???? Are you planning to just drive through these towns so you can legitimately tell friends at home that you went there? LOL<BR><BR>We are not slow travelers, but found 2 cities in 1 day to be somewhat exhausting. So much to see and do in every town you mentioned.<BR><BR>

Hi Tom! Unless you are going to Deruta for ceramics, I would skip it. It's not a hill town, it's a manufacturing town and looked like one. We did not find anything charming about it.