Tuscan Hill Towns

You may find these articles by RS helpful.

• www.ricksteves.com/watch-read-listen/read/articles/hill-towns-of-central-italy
• www.ricksteves.com/watch-read-listen/read/articles/volterra-and-san-gimignano-hill-towns-with-a-twist
• www.ricksteves.com/watch-read-listen/read/tms/siena-italys-medieval-heart-and-soul

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I'm not surprised if you are undecided. There are 287 municipalities (or "communes") in Tuscany, with an average of 8 "frazioni" (towns & villages) in each one of them. Most of them are on top of a hill.
These are some you might consider (in no particular order):
Siena
San Gimignano
Volterra
Pienza
Montepulciano
Monteriggioni
San Quirico d'Orcia
Certaldo
Pitigliano
Sorano
Massa Marittima
Arezzo
Cortona
Greve in Chianti
Castellina in Chianti
Poppi
Anghiari
Bagni di Lucca
Vinci
Gavinana
just to name the ones that first came to my mind.

Take a look here: www.borghiditoscana.net/eng/
Go to the left pane ("Index of villages of Tuscany" by province), click on each and choose what you like best.

We took in Certaldo (quiet), San Gimignano (touristy until mid afternoon), Volterra (great) and Orvieto (great.)

We also visited Siena, which is a busier, large city. We found parking difficult there, and the city surrounded by modern apartment complexes that were very congested. If I was doing it again, we'd go into Siena on a bus from Florence.

Our favorites were Montepulciano and Pienza. Also loved Assisi but that's not Tuscany.

For classic hill towns, Montepulciano was our favorite. Pienza, only 20 minutes away, is very charming too. Volterra is also fabulous. Great Etruscan and Roman remains. If you go to Volterra, it's hard to skip nearby San Gimignano. I agree it's much more touristy, but distinctive and still worth a visit.

There's an embarrassment of riches when it comes to hilltop towns in Italy, even more so if you don't limit yourself to Tuscany. For example, you'll find the beautiful Orvieto and Assisi in neighboring Umbria. (From Orvieto, you can spit and almost hit Tuscany.) We thoroughly enjoyed both of those, and they would each easily hold their own in a head-to-head contest with any town in Tuscany.

Reminds me of Will Rogers "I never met a man I didn't like."

Did you ever visit an Italian town you didn't like? I surely haven't.

This is really a tough question as we do not have any additiional information. We have been to many of the town's on Roberto's list and had great experiences at all of them. Montepulciano is one of my favorite wines, so I thoroughly enjoyed both my trips to that town. If you're like alabaster or would enjoy seeing an artisan at work, Volterra may be an option. Siena is more of a small city than town, but we had great times each of the times we went there. Attending the Palio was one of my most memorable experiences not just in Italy but in all of Europe. I would recommend that you do some research as to what towns appeal to YOU the most. The towns of Greve and Castellina are great especially if you enjoy Chianti Classico.

I do want to second another poster about Orvieto, while technically it is an Umbrian town, the Etruscan ruins and caves, the Cathedral, and general layout of the town make this another enjoyable town. We spent 1 night there in between Florence and Rome and easily could have spent another night. Keep in mind that even though distances may be small, travel times are frequently deceptively much longer.

If you like wine I would add Montalcino to Roberto's list.

Been to Siena, San Gimignano, and Lucca. Would recommend only the first two. I wish I'd picked Volterra, Montepulciano or similar instead of Lucca.

I've been to Siena, San Gimignano, and Assisi with Assisi being my favorite. If you do go to Siena or San Gimignano take the bus. Hard to figure out the bus schedule but it does drop you off right in town. Have fun.

How do you plan to travel? Hill towns are not accessible by train for the most part and bus service is designed for school kids not tourists, so to really have access in this region you need a car. If you don't have a car then base in FLorence and do organized tours. Or perhaps base in Siena which is a lovely place but not as well connected as Florence.

We have stayed in an apartment within a half mile walk of Lucignano, in a small hamlet near Siena -- each for a week and spent two weeks recently in Montepulciano. In each case we had a car and used the rental as a base for exploring the region. The Val d'Orcia is the most scenic area and I would base there at a place with parking and easy access in and out and then travel to gardens, abbeys and hill towns in the region. I loved basing in Montepulciano because it was well located for regional travel but then in the evening we had a charming town with many many good restaurant options within an easy evening stroll. You can't drive after any drinking in Italy, so basing near your dinner options is a good choice.

How do you plan to travel? Hill towns are not accessible by train for the most part and bus service is designed for school kids not tourists, so to really have access in this region you need a car. If you don't have a car then base in FLorence and do organized tours. Or perhaps base in Siena which is a lovely place but not as well connected as Florence.

We have stayed in an apartment within a half mile walk of Lucignano, in a small hamlet near Siena -- each for a week and spent two weeks recently in Montepulciano. In each case we had a car and used the rental as a base for exploring the region. The Val d'Orcia is the most scenic area and I would base there at a place with parking and easy access in and out and then travel to gardens, abbeys and hill towns in the region. I loved basing in Montepulciano because it was well located for regional travel but then in the evening we had a charming town with many many good restaurant options within an easy evening stroll. You can't drive after any drinking in Italy, so basing near your dinner options is a good choice.