Hill towns are nearly a symbol of Tuscany. Many seem to grow organically out of the hills they're perched upon. Indeed, many of the towns marked on the map below have risen from the rocks and cobbles that were collected when the hill was flattened for building. Regional, vernacular architecture gives them a visual signature, and the winding streets seemingly formed from existing animal trails bring it all together. Perhaps we love hill towns because they arise from nature, helped along by a sympathetic human hand.
The hill towns mapped below are listed by provinces. Provincial capitals have the red symbols. A couple of provincial capitals are hill towns themselves, like Siena and Arezzo, marked in bold type.
These are not all the hill towns in Tuscany. They are the ones we've found to be the most interesting.
Fosdinovo is one of the many castled towns in the Lunigiana historic territory of Tuscany. In a rather dramatic fashion, it lies along a ridge with a view to the sea. The small town can be visited on a day trip. You might combine it with a trip to the marble quarries. It's 10.6 miles from Carrara, the starting point of our Marble Tour. Fosdinovo is 15.3 miles from Massa, about a 25 minute drive. It's pictured below.
The hill town of Barga is an hour and 16 minute drive from Fosdinovo over winding mountain roads passing interesting small towns in the Garfagnana territory. Barga has a Scotland connection. It's where Barga's workers went following the demise of its silk industry and you're likely to hear more English spoken than you'd expect in an out of the way place.
Montecarlo is a wine producing town near tourist favorite Lucca.
Lari is one of the prettiest hilltowns around. It's even pretty in the Google Map view. If you favor the pasta in the bright yellow package, then you'll be happy to know that Lari is home to the Martelli Pasta Factory. The castle in the center of town hosts an interesting look at how torture was made a part of the legal system of the time. The castle was a prison until well after WWII. You can see the whole deal in a long day, and there's a couple of great places to eat for lunch.
San Miniato is known for its fall truffle fair in November, but is quite a nice example of a medieval hill town. All of its museums can be visited with a single, inexpensive ticket.
Judy Witts Francini holds her famous cooking school in the charming Certaldo when she's not taking it on the road.
San Gimignano you know. Prickly with towers.
Volterra is a walled hill town 20 miles from San Gimignano where you can really get a taste of its Etruscan, Roman, and medieval roots.
Poppi An interesting hill town built around a castle, the Castello Pretorio, 13th century, with the "Devil's Tower" alongside. The Church of San Fedele was originally a monastic church built for the Vallumbrosan Order in the late 13th century. Poppi is on the way to another hilltop destination: La Verna, a religious pilgrimage destination on Monte Penna where St. Francis received the stigmata.
Anghiari is always at the top of the heap when evocative hill towns are being discussed. Anghiari is about 20 miles east of Arezzo and near the border of Umbria. Arezzo is on a main rail line so if you’re using public transportation.
An inhabited hamlet since the Etruscan period, Monte San Savino was developed in the Roman period. Artisan ceramics can be purchased here as well as some of the area's best porchetta.
Siena itself is a hill town surrounded with about 4 miles of medieval walls. it's best known for its large fan-shaped main square, Piazza del Campo, and the summer palio horse race that’s run in the square.
Montefollonico is a very interesting little hill town that lies on a hill in a strategic position between Valdichiana and Val d'Orcia. The town was likely named after Roman clothes washers; Roman cloth-launderers were called fullones and they sometimes used urine to get things really clean. From here it's an easy drive to wine town Montepulciano.
A little further on is the ideal Renaissance town of Pienza built on a small rise and thus qualifying for hill town status. Further on is another wine town built on a hill, Montalcino.
Monteriggioni is girded in a complete wall that can be seen from the highway passing below it. The intact fortified wall allowed guards to patrol and protect the town inside. It has 2 gates, one called the Franca or Romea Gate which faces Rome and the other the Florentine Gate facing Florence. In july, Monteriggioni celebrates its medieval heritage.
In Tuscany's Maremma territory, you'll find some interesting hill towns that feature Etruscan mining. The Medieval Hill Town of Populonia is a small gem that sits above the Archaeological Park of Baratti and Populonia, between San Vincenzo and Piombino on the southern coast of Tuscany.
A short drive away is Campiglia Marittima, a medieval hill town with castle ruins, flowers, narrow lanes, and very good food. Just a little further inland in the Val di Cornia is Suvereto where wines designated Val di Cornia Suvereto are grown. The village is called one of the most beautiful towns in Italy.
Pitigliano, known as "Piccola Gerusalemme", or "Little Jerusalem", is one of the most spectacular vistas you'll come across while driving in a car. Around Pitigliano and nearby Sorano you can walk the Vie Cave, the Etruscan sunken roads.