Best home base for Tuscany Hill Towns

your choice of Orvieto is excellent

It largely depends on which places you want to visit. Since you have quite a bit of time at your disposal you should choose more than one base and cover the area around each.

Orvieto is a nice place, but it would not be my choice to visit Tuscan towns as Orvieto is located to the south in Umbria, at the border from Latium, and frankly a bit of a distance from Tuscany to make it a good choice. Orvieto is good for visiting Orvieto, Civita, Todi, and maybe places in southern Tuscany, like Sovana, Pitigliano, Saturnia.

The area near Colle Val D'Elsa/Monteriggioni, is very central for Siena, Chianti, Volterra, Monteriggioni, San Gimignano, Certaldo, etc.

Cortona is central for Cortona (obviously), Arezzo, Lucignano, Anghiari, and also the Northern Umbrian towns (Castiglion del Lago, Magione, Perugia, Assisi, Spello, Gubbio).

Montepulciano and Pienza are good for that area in the Val D'Orcia, including Buonconvento, San Quirico, Montalcino, Chianciano, etc.

With 30 days, you might consider a couple or three base towns to make it easier to explore the regions. Orvieto or Assisi would be good to explore Umbria while Volterra might be a good spot to explore Tuscany. I would throw in Lucca as a third option to explore that area. Do you plan to rent a car or only use public transportation? That might make a significant difference in where you choose your home base.

If you want to visit as many hill towns as you can, you will need to move beyond RS' recommendations. Try Michelin (especially if you have a car), Lonely Planet, or some other more comprehensive books. RS is great for turn-by-turn views of his favorite places, but there are hundreds of other places to choose from.

Orvieto is only a two hour drive to Florence. You have all of Tuscany in between.

We liked Montepulciano and Pienza. They are quiet and small but beautiful. Lots of good wine and cheese made there and we travelled to Assisi, Siena, San Gimignano, Montalcino, etc. all by car about an hr. to 90 minutes away from Montepulciano. Probably 90 minutes from Florence by car as well.

I prefer a smaller hill town. Last time we did this we spent two weeks in an apartment right at the wall in Montepulciano which had parking. We had our front door in town and could stroll to dinner in the evening (you don't want to be driving after dinner if you drink at all -- laws are much stricter in Italy than the US on drinking and driving). During the day we could easily drive to many other towns, abbeys and gardens in the region. It was a great town to be in and a great base.

I don't like to use larger cities if I have a car; even Siena is a big city and you go through miles of urban sprawl to get out.

If you won't have a car then choose a larger town like Orvieto or even Florence which has the best train connections. Hill towns don't have train stations for the most part. If you want to see the best of Tuscany you need a car.

Unless you will rent for a month which is usually a bargain, I'd consider two bases during that time.

We were based out of Montecatini Terme recently which provided easy access by car or rail to virtually everything. It is no hill town, but the old city Montecatini Alto is also lovely. It's on the Autostrada so you can also connect to Florence, and the sea towns easily.

We visited Volterra, I would love to base out of there sometime!

Cheers!

We also based in Montecatini Terme for our 8-day visit to Tuscany. It was convenient for transportation by car and train. As the other poster noted it's a newer town (not an ancient hill town) but the hill town above it, Montecatini Alto, is easily reached by funicular. While there we were able to visit: Pisa, Florence, Siena, Lucca, Cortona, Arezzo, San Gimignano, Volterra, Prato, and Pistoia - not all hill towns but great places to see.