Hill Towns

We had a lovely day driving from Siena to Monteriggioni and Volterra. Monteriggioni is very small, but with intact walls and quite medieval in feel, quiet and picturesque. you can climb up to the ramparts for an amazing view. Rick Steves has covered Volterra quite thoroughly in his book: charming, historical town, also with amazing views. We skipped San Gimignano in favor of these two.

I've always been partial to Pienza. Medieval and rustic, but with some Renaissance flourishes. Same for Urbino, which has the added benefit of being a bit more off-the-beaten-path. The beauty and spirituality of Assisi can not be beat.

Assisi, definitely, and not far away is Spello (about 7 km), a small medieval town that has a flower festival every year and all the residents decorate their houses (this is late spring/summer). In Assisi, don't miss the Rocca Maggiore, an old fortress that overlooks the valley. Other places near Siena: Todi, a lovely medieval town with a great central piazza and great restaurants.

So many great places, so little time. I tried to pick a variety. The only one I regret spending time at was Lucca, it's flat and shouldn't be considered one of the "hill towns". Lucca is probably a great choice for mobility impaired people, but not nearly as beautiful/inspiring/romantic, IMO, as the true hill towns. The one that was the most pleasant surprise, for us, was Orvieto in Umbria. It sits on a cliff, rather than a hill, and has a large Cathedral as well as tunnels you can tour below the city. I also liked San Gimignano even though many consider it too touristy. I thought it was a great example of a medieval town (even if much is reconstructed). We were there in late October so the tourist crowd was manageable (it might be too much in summer).

Pienza.....great roast pork sandwiches...built by some Pope or other and stunning.

Pienza's main square was designed for Pope Pius II and was completed in three years in the mid-1400s (1459-62). Pius II was born in the town which was renamed for him.

Cortona: charming, scenic, and great food...

I loved Orvieto; there are many interesting activities there. Definitely take the underground tour. You can also enjoy the views from the top of the Torre del Moro or climb down to the bottom of St. Patrick's Well. The facade of the Duomo when the sun strikes it is absolutely stunning. I also loved Pienza; I discovered my love for a certain variety of Pecorino cheese sold there and I loved sampling the cheeses & walking around the town. I would also sugest visiting Volterra. I really enjoyed it. We had a half-day tour with Annie Adair, a guide that Rick Steves featured in his show about Tuscany. Even if you don't elect for a tour, it's a very interesting town. You can view a Roman amphitheater. We enjoyed visiting the alabaster workshops and seeing the many incredible alabaster pieces available for sale. I also liked the Etruscan Museum there. As mentioned previously, Lucca didn't really excite me as much as I had hoped. It is a nice town but just didn't interest me as much as the others. Have a great trip.

We also loved Orvieto and Pienza. San Quirico is a wonderful smaller town with easy and free parking. Not a huge fan of San Gim-maybe because of the crowds-just does not appeal as much as other towns. Not a hill town but Radda is a nice little town.