Advice needed - how many days to explore Hill Towns

You've asked a pretty broad question - the answer depends on your flexibility and interests. And where you are staying. And, what is a "few" days?

I would say three days. Allow a full day for Siena and divide the other towns into the other two days. But be sure to give yourself time to just hang out and drink wine in a sunny spot.

I want to stay somwhere in Tuscany that is centrally located between these towns (still to be determined, like an agriturisimo or B&B...any suggestions?) and then drive to these towns. My main focus is photography and really getting to explore the back streets, climb look-out towers for the views, etc. I was thinking 3 full days as well. I'm not sure how big the towns are and how much time is needed to partially saturate each town without rushing too much. Thanks for your advice.

I did exactly what you are interested in except I did not have time for Volterra in my 3 nights. I stayed in Siena and took buses it was easy and low cost. Save euros and rent the car when you lv Siena if you still need one. If you decide to see Umbria also you will need the auto and of course more time. It is the logical thing to do if you can. Asssi, Orvieto and great.

I'd make Siena (or nearby) your home base for your trip. We really liked Montepulciano and Sienna. Montepulciano was my favorite. (Though we didn't see all the towns you listed). Pienza is extremely cute, but it is very small- we walked the entire town in way less than 3 hours.

I think that 3-4 days would be enough, and I would devote an entire day and evening to Siena. Driving from Montepulciano to Pienza is a pretty short drive. Taking the motorway between Sienna to get to Montepulciano will make the driving considerably shorter.

Are you driving yourself? Do you have a navigator? It was not too bad driving, but having a navigating partner is key to making good time between the towns. Streets are fairly well marked, but we still missed a few turns.

As PP said- time required for the hill towns really depends on your interests, and your personality as well. We spent 4 nights outside Cortona and loved it. It was really relaxing, and just what we were looking for.

Thank you for your suggestions. I am researching B&B's & Agriturisimo's in the area and would like to stay somewhere near Siena as you suggested. As for a navigator, we are planning to use a GPS...the only thing I'm unsure of is whether it will navigate us from town to town without an exact address...I'll have to do some research. If anyone has been to Volterra, can you give me an idea of how much time to devote to it?

Sheron,

My preference to visit five (and possibly more?) hilltowns would be more than three days, given that your primary interest is photography. That's also a major factor in my travels, and I've found that it's necessary to spend some time in a location in order to capture different lighting conditions. Also, the character of towns changes at night, sometimes dramatically. I'm wondering if "a few days" will be adequate time?

Good luck!

I think you will need more than 3 days - a week is always necessary for me. And I would stay in an agrotourismo in the area. When we have a car in Italy we always stay out of a town so we have no parking or traffic issues. As you drive in Tuscany you will pass many towns you will want to explore so you could end up seeing a dozen towns on your trip.

I spent a week in Certaldo Alto (alto meaning the upper town) last summer and loved it - in fact, I ran into a RS day tour there. It is quite near S. Gimignano and is a comparatively undiscovered & beautiful hill town, wonderful architecture. There are some tourists each day (hardly any Americans) but not enough to be crowded, at least not in May when I was there. I stayed in a wonderful apartment built into the ancient walls of the upper, walled town.
If you have a car, you are given a 'remote' to raise & lower the James Bond-type posts that block the road to the upper town!

We like to wander and take pix too, so to us three hours in any town, except the very tinest, is too short. Some people say three hours is plenty of time in Assisi, but we were there all day. We spent an entire day in Siena and it wasn't enough. We spent five hours in San Gimignano on our first visit, especially nice after the last tour bus leaves. (P.S. They have the best gelato.) I think getting to Volterra took us half a day (well, just kidding, but it's up there on a long winding back and forth road), but we only had four hours there, because of another commitment, and it was not enough. Great views. I'd allow more days than three, and you may discover some towns take more time that you figured, some less, or you may decide to visit one not planned on, that way you'll have more flexability.

I'd say 1-2 towns per day is about the right pace. You want time to walk around, linger for lunch, relax and have a cappuccino, browse in shops, visit the church, maybe take a guided tour. So I'd say 3 days.

All of these suggestions are good. The best one is to be sure and allow time to explore that which was not planned. So many towns - so little time!!!!! My favorite times are those spent in "found" places...

Sheron,
we have just returned from a month in Italy and had 4 days in a B&B 20 km south of siena which is a dlightful city and worth a whole day and evening. we drove and did 2 hilltowns per day. Our personal favourites were Volterra which is easily combined with San Gimignano and Montepulciano which can be combined with Montalcino. The drive is seldom straightforward as street signs were devised by someone with a sorry sense of humour. (like arrowws that point up the hill face rather than left or right) but the drive and scenery is part of the fun so relax and enjoy. In October the roads were not too busy. we loved Tuscany and also had 3 nights in Florence. If you like museums you would not have much time for exploring outside the town.cheers

we stayed in siena and visited all of those listed above plus montalcino and cortona in 2 days with a car. we did take out time and enjoyed all of them very much. my fave was pienza my wife's was sam g.
good luck :):):)

Warning: We had big plans to see lots of hill towns. Then we got to Casa Nova- our agritourismo in Greve-in-Chianti and we loved it so much we didn't want to leave. We ended up cutting back on how many hill towns we went to just so we could relax and enjoy Casa Nova and Greve- The good news: We have no regrets.