What is "best" hill town to visit after San Gimignano & Siena?

Not an expert, but we enjoyed Artimino, west of Florence. A walled, medieval, hill town with a Medici villa and three excellent restaurants. Apartments that are converted from the old stables. Shops for gelato, wine etc. but not the souvenir vendors of bigger venues. Close to Vinci. Just a thought.

Urbino is an extremely interesting hilltown, but in Umbria, not Toscana (is you are not overfixated on regional borders). So are Gubbio and Camerino, Umbria and Le Marche respectively.

I too love Tuscany and the hill towns. We stayed in Siena in 2010 and we are one of the few that found it overrated. My recommendation would be to stay in Orvieto. From there it is an easy drive to Civita and Montepulciano. I would agree with a day trip to Gubbio, a small village with a lot of history and an thrilling tram ride to the Duomo at the top. My other recommendation would be to check out an Agriturismo to stay in. That would give you an "old world" experience.

Pete, excellent recommendations so far (Urbino is actually in Le Marche). Todi and Spello are also in Umbria and both beautiful examples of medieval hill towns. Spello is only a few kilometers from Assisi, (Assisi might be too touristy for you base, but definitely worth a visit). Keep in mind the potential fines for driving in restricted areas in the cities.

Just spent 5 nights in Spello and we are in love with that charming, medieval Umbrian town! 8 minutes by train to Assisi, which is indeed worth a visit as Zoe says. Also a short ride to Spoleto, by the way, another stunning place. The wine in the region is not widely known but is excellent, Sagrantino di Montefalco. Can recommend a wine tour if you are interested: Gusto Tours. But if Tuscany is where it needs to be, take a look at Montalcino and Montepluciano. Both are wine centric, but charming, especially at night. And Orvieto, as mentioned, is a great option too. So many places, so little time!

Consider Orvieto. It's just over the Tuscan border, in Umbria, north of Rome. We absolutely loved it and wished we had stayed three nights instead of two. Here are some photos and a couple of short video clips of our trip to Orvieto in May 2011 that show a little of what we enjoyed. Rick has good info on Orvieto in his Italy book.

I think just about all the Tuscan towns are hill townswith walls around the cities. They took their politics seriously in 1450 AD. The town of Volterra is a short distance south of San Gimignano, and its history is incredible. I suggest finding a good hotel or B&B outside one of the towns south of Florence, and just ramble from city to city taking day trips. Country accommodations are also more reasonably priced. Tuscany is a trip in timeback as far as 450 BC. I saw a house in Tuscany on HGTV International House Hunters that was built in 1100 AD. That's old enough.

One place that is very easy to get to (the train station is accessible to the town, unlike Montepulciano etc) is Arezzo. Message me if you are interested, I have lived there for several months and love the city. I would particularly recommend it if your time in Italy falls upon the Joust which takes place in June/August, or if you could make it the first weekend of the month on which there is an Antique Fair that is now famous throughout Italy. (And started by my relative!)

I'd go with either Volterra, but some towns mentioned here are new to me. Glad to see no one suggested Lucca. Lucca is an only okay town that is flat, not a hill town. It has a decent wall turned into a park. The wall is brick, however, and doesn't have the signature medieval stone look of, say, San Gimignano. I'd only suggest Lucca for someone with ambulatory issues who has trouble managing the real hill towns.

This is really a matter of personal preference...so I'll give you my preference, and explain why so you can determine if it matches up to your interests, etc... I'd recommend Volterra, because it has the medieval quality, with some nice sights as well. I found the Roman theatre ruins to be very nice, built against the hillside, some parts not so intact, but other graceful remnants were quite beautiful. The local museum has interesting etruscan artifacts if that appeals to you, and dramatic views on the edge of the town. (Plus some churches, town halls, etc.) I'd also recommend Orvieto, because of the impressive church, especially picturesque alleys/streets to ramble, and most interesting for us was St. Patrick's well (discussed in RS book), an architectural/historic marvel, fun to explore, awesome to see. There are also underground tours that looked fun, but we didn't have time. I've also visited Montepulciano, Pienza, Lucca, and Monterrigioni (sp?), and liked them also, but wouldn't put them at the top of my list. (We've also visited San Gimignano and Siena too, but you've already been there!) Have a great trip!

bookmarking!

My choices would be Volterra, Orvieto or Montepulciano. Definitely 3 of my favorite hill towns. We loved Volterra so much we got married there!