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Medieval Tuscany: villages and towns to visit

Medieval Tuscany: villages and towns to visit

Tuscany is one of the regions where the medieval imprint is most present, traces of which can still be admired, as well as many relics. Some medieval villages in Tuscany are perfectly preserved and visiting them is a bit like taking a trip back in time.

The Middle Ages is one of the most fruitful periods for this region, which has left us numerous art forms but above all architectural and urban masterpieces. The major centers and progenitors of Medieval architecture are definitely Florence, Siena and Pisa, although with quite different styles. The historic centers of these cities are a succession of medieval buildings and testimonies.

But what are the most beautiful medieval villages in Tuscany to visit?

Here is a brief overview of medieval towns and cities in Tuscany.

Medieval villages in Tuscany: which ones to visit?

Tuscany is therefore one of the regions with the most medieval evidence.

There are so many towns and villages to visit, and one of the advantages is that they are all easily accessible. In fact, Tuscany is a region that allows you to reach practically any area within two or three hours at most: this means that in one day you could visit many small medieval villages throughout Tuscany.

Here are the most characteristic ones divided by area.


The Val di Chiana is an area of Tuscany rich in beauty and medieval treasures. In this valley enclosed between Arezzo, Siena and Perugia are some of the most beautiful medieval villages in the region.

Montepulciano is one of the main centers in this area, enclosing within its ancient walls a town center full of historic buildings. Then, on top of a small promontory stands Cortona, where Etruscan, medieval and Romanesque art meet: the Archaeological Park is one of the must-see stops, a true open-air museum. Finally, there is Castiglion Fiorentino: the whole village still retains its typical medieval structure.

If you want to go deeper and find out what there is to see in Val di Chiana, read our dedicated article.


And then there is the Val d’Orcia, the hills around Siena that look like something out of a postcard!

If you want to visit this area, you can’t miss San Quirico d’Orcia, with its historic center characterized by no less than 14 perfectly preserved towers that mark the path along the medieval walls. In the same area we find Bagno Vignoni, world-famous for its fountain from which flows thermal water that comes from the volcanic springs below; this very water has been known since the time of the ancient Romans.

Around Siena, of course, there is also San Gimignano, while moving toward the coast we find Volterra.


Of course, there are also the larger cities that have a typical medieval feel and are worth visiting if you are planning a vacation in Tuscany. For starters, there is Florence, with its historic center full of tower houses and its civil and religious buildings typical of the Medieval era such as Palazzo Vecchio or the Bargello, but also real parts of the city such as Piazza Strozzi.

Equally beautiful is medieval Pisa, Siena and of course Arezzo: Arezzo itself preserves some castles and parish churches in perfect condition.

Staying in a medieval castle in Tuscany

To plan a perfect medieval-style vacation, even the accommodation you choose for sleeping should be themed!

There are many medieval castles in Tuscany that offer sleeping accommodations, but not all of them are preserved to give you the true medieval atmosphere, the one that will take you back in time.

Gargonza Castle is a small medieval village nestled in the hills of Val di Chiana, halfway between Siena and Arezzo, a few kilometers from Monte San Savino. It is an ancient fortified agricultural village, with its newly restored tower, walls and a 13th-century gate. In addition, there is a small 13th-century Romanesque church that can now also host ceremonies for those who want a princely religious wedding.

If you would like to book your stay in the medieval castle of Gargonza in Tuscany, contact us.

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