we will be arriving in milan july 25th. we would like to drive,avoiding larger cities like florence, and base ourselves for a couple of days, and take day trips from this base. then we would move on and repeat. cities around siena would be fun and then possibly umbria or piemonte. we have been to cinque terre, love it but do not want to repeat it. it has been difficult for me to come up with a driving plan and where to base ourselves for day trips. i have read ricks book, which will be a great help once we have a plan. any help would be soooooooooo apreciated . thank you
You didn't mention if you were flying out of Milan as well as arriving, or how long you would be gone. That may make a difference on how far you travel south in Italy. Piemonte is reachable from Malpensa Airport in Milan in about two hours, and I would suggest staying near Asti. There are so many beautiful hill towns and wineries nearby. Agriturismo accommodations are everywhere, and staying in one really lets you experience rural Italian life. The area around Siena or Siena itself is a great base for excursions to Pisa, Florence and the Tuscany countryside. If you travel as far as Umbria, I would suggest staying in small towns such as Gubbio or Assisi.
Locanda Rosatti is just outside Orvieto. It is a perfect base for Tuscany and Umbria. They offer breakfast and dinner. It is owned by brothers, one of which is a world class cheif. The food was amazing. The grounds were gorgeous with an orchard and rose bushes. They have a nice big pool and you can see the duomo of Orvietto from the back of the property. http://www.locandarosati.orvieto.tr.it/
This is probably my favorite place I've ever stayed in Italy.