My husband and I will be spending 11 exciting days in Italy, over Easter, this year. 4 nights will be based in Tuscany, in an Agritourismo between Sienna and Florence. Wed like to spend a day just meandering. Wandering through the hills and down dirt roads. Maybe pack a picnic and get lost... Lol any ideas of where to drive? Which direction? To which small off the map towns? We love history, Churches, and could be convinced to try the local wines and food!!! Lol. Thanks in advance!
I suggest San Gimignano, Volterra and Certaldo--since they're in the same direction. They're to the west.
Picnic supplies are best gotten in two mega supermarkets in Poggibonsi if you're close. Otherwise, every city of any size will have a smaller supermarket. (We did most of our own cooking while at an agriturismo apartment.)
I'd suggest you read some travel guides on Tuscany about other hill top cities. After you get there, you'll find just rambling from city to city without any plans is a preferable way to see the area.
Monteriggioni is a nice walled, small village that seems to be off the beaten path. Have some delicious pappardelle with wild boar at the Il Pozzo restaurant there (it was once featured on Rachael Ray: http://www.youtube.com/watch?v=T2NE3G1weUg).
To the south is beautiful Orvieto (take the funicular up to the hill-top town, do the RickSteves walking tour, visit the Duomo, sit in the piazza and drink some Orvieto Classico while you look at the Duomo facade sparkle in the sun), and near there is Civita di Bagnoregio (a tiny, traffic-free hilltop village, accessible by a long pedestrian bridge/ramp). Both are described in the RS travel guide.
Arezzo is a nice Tuscan city. Churches include San Francesco where Piero della Francesca's Legend of the True Cross fresco cycle is located. One of Cimabue's crucifixes is in San Domenico. The Duomo and the Piazza Grande is nice. The park (Il Prato) at the top of the main street (Corso Italia) provides a beautiful view over the Tuscan hillside. Be careful of the ZTLs within the city walls, but I believe there is parking around the train station (I never drove while I was there, sorry!).
Thank you for your ideas. We really like the Civita/Orvieto idea. RS does a beautiful job of describing this area. I am so looking forward to a day of just driving and seeing where we end up. Thanks for the thoughts...