Hill Towns in Italy

Do you have any guidebooks for Italy? If not, I suggest getting the Rick Steves book on either Italy or Florence/Tuscany. He talks about his picks for the best hilltowns to visit, and lets you pick the ones that most interest you.

I presume you don't want to include Florence, otherwise you'll need a couple of days just for that. In Umbria: Assisi, Perugia, Gubbio, Orvieto, Spoleto. In Tuscany there are too many towns. I'd also suggest to do some research online and see what you might like. I grew up in Florence and the ones I used to visit a lot on short getaways with my friends and family are: Siena, San Gimignano, Volterra, Monteriggioni, Pienza, San Quirico, Montalcino. On the Aretino area, there is Cortona, Arezzo, Anghiari, the Casentino valley. Along the coast, Pisa is a must (although not on a hill) and further south in the Grosseto province, the Maremma region, with Capalbio. Around Florence/Pistoia you can see Fiesole, Vinci (with Leonardo's house), Montecatini. In the Lucca province there are numerous towns worth seeing like Lucca itself (not on a hill but very pretty) and the Garfagnana valley. The Apuane Alps near Carrara are also worth seeing.
Four days are enough to see a few, but you can't hit every hill town in Tuscany. Tuscany has 287 municipalities and each has several villages within its limits. So we are talking thousands of hill towns and villages. I haven't been able to visit all in 30 years I lived there, so you won't be able in 4 days. Take a look here. It can give you some clues of what you might like http://www.borghiditoscana.net/

Vist the Roman ruins of Carsulae, by San Gemini, in Umbria. A real hill town close by and very small, Cesi! Todi, Montefalco, Spoletto, Assisi, Orvieto are all good.

Todi would be a beautiful town to visit in Umbria. If you visit Assisi, Spello is only a few kilometers away.

Just returned from a 13 day trip visiting exclusively the hill towns of Tuscany and Umbria. Everyone that has responded to you is spot on with their recommendations. We are fortunate to have the Rick Steves Helpline available. Have often said that you can read the best tour books, see the most interesting documentaries, surf carefully the Internet but there is NO substitute for the opinions of someone that has been there and whose opinions you can trust. And that is exactly whey this Helpline is so invaluable. Good luck!

PS. The nice thing that we did that might be of help to you is that after 3-4 days we were still not that far from the tollway; therefore if time becomes a factor which it usually does you can hop back on the tollway and make it back to Rome to meet your tour. If you are returning the car to the airport, this is important. There are NO SIGNS that read; Return your rental car here. Look for the big red building near the main terminal when you pick up the car. To that building the car must be returned. There is only a lane that reads something about returning your car there. Being from Chicago and O'Hare aiport, I was really aggravated. If you haven't rented your car yet, I am pretty good buddies with Auto Europe and its owner. They are the big guys in European car rental and rightly so. You will probably not need a GPS so don't spend any money there. Be prepared when checking the car in for the 3E a day road tax. I use my Visa card for the collision waver so I don't need insurance. When you get down to the brass tacks of the matter, if interested, I will tell you where we stayed in Bagnoregio and Montalcino. Nice little B & B's about 60E a night as I recall. Included a good breakfast in Bagnoregio - In Montalcino it was not included but a neat little "bar" next door; had a coffee/pastry and we were all set. Good thing about this B & B was it had free parking close by. Richard