Tuscany is one of the most wonderful regions both in Italy and in the world. It is a place where you can visit amazing historical and artistic cities, spend your time in fairytales countrysides, explore villages with enchanting landscapes, and taste delicious local wine and food.
Most tourists come to Tuscany to see very popular cities like Florence, Siena, Pisa, or Arezzo. But, everyone should at least once visit some smaller, often unrecognized villages where time stopped and where you will feel true Italian medieval life.
Even though there are many beautiful Tuscan villages, we will show you 5 that you should not miss in this article. All of them are very close to each other, so you can see them all even in a single day if you will have good time management. Here are 5 of the best small villages in Tuscany, starting from the north to the south:
San Gimignano
San Gimignano is a beautiful medieval village with slightly over 7,000 inhabitants in the province of Siena. It is located more or less in the center of the ideal triangle that connects cities Livorno, Siena, and Florence and is a few kilometers away from another magnificent village called Volterra. San Gimignano is so important that its historical center is included in World Heritage Sites protected by UNESCO.
The whole village has retained the overall appearance that it had in the thirteenth and fourteenth centuries, so it is nowadays one of the best-preserved examples of medieval villages in the world. Historically, the village has Etruscan origins, but its development began just after the year 1000 thanks to its favorable geographical position and saffron production, which was sold throughout Europe.
Manhattan of Middle Ages
In the Middle Ages, San Gimignano had more than 70 towers built above houses of wealthy medieval families. Therefore, this village ironically got the name “the Manhattan of the Middle Ages.” Nowadays, only 13 towers left, but they still make San Gimignano unique among other Tuscan villages.
Besides towers, the symbol of the village is a beautiful Romanesque cathedral covered in impressive frescoes made by Domenico Ghirlandaio and Jacopo della Quercia.
It is located right in the center of the village, which is a place where both locals and tourists hang around, enjoy a delicious ice cream or relax on the terrace of a few bars.
An extraordinary experience is definitely strolling among small, narrow, medieval streets, as well as climbing Torre Grossa for an outstanding 360-degree view of nearby hills. There are numerous small shops with authentic local products, mostly wines, cheeses, hams, pasta, and liqueurs for those who like shopping.
Read more: San Gimignano travel guide
Volterra
Around 15 kilometers (9 miles) east of San Gimignano, there is Volterra, another small gem with only 10,000 inhabitants. This lovely village is located in the province of Pisa, and it recently gained huge international recognition because there were shot some of the most important scenes of “New Moon,” the second movie part of the famous “the Twilight Saga.” Volterra also has Etruscan origins, but the villages became known in Roman times, while its most significant economic power has gained in medieval times.
Nowadays, most historical monuments in the village are medieval, such as the beautiful Romanesque Cathedral built between the 12th and 13th centuries. In front of the Cathedral, there is also the valuable Baptistery of San Giovanni and the Palazzo dei Priori which looks very similar to the Palazzo Vecchio in Florence. All these wonderful attractions are located on the Piazza dei Priori, which is one of the oldest areas in all of Tuscany.
Also worth visiting is The Roman theater from the 1st century BC, which was excavated in the 1950s, as well as Etruscan tombs located in the Valle Bona area. Furthermore, Volterra is known for its historic workshops where alabaster is made.
It is a soft mineral or rock, often used for carving, and was the main source of economic development for several centuries in this small village. Those who love art should visit the art gallery in Palazzo Minucci-Solaini that exhibits mostly beautiful works by Tuscan artists from the 14th to 17th centuries.
Read more: 25 things to do in Montepulciano
Cortona
Cortona is a lovely village located in Val di Chiana, in the triangle area between Siena, Arezzo, and Orvieto. This village was also known between the eighteenth and nineteenth centuries when it was praised by Goethe and many other intellectuals who were enchanted by the beauties of Tuscany and this area. Even though Cortona also has an Etruscan origin, most of the preserved architecture is from the Middle Ages.
The village has a hilly structure with many streets that constantly go up and down, typical for Tuscany. The most popular place in Cortona is definitely the Piazza della Repubblica. You can find many locals hanging around, sitting in the bar, drinking cocktails, or leisurely strolling around the square. The most photographed monument in Cortona is Pallazo Comunale, built in the 12th century, which is also located on this vibrant square.
Piazza Signorelli is another beautiful square in Cortone where you can spend some quality time. It is bigger than Piazza della Repubblica, but it also has many bars and restaurants which are great for relaxing after a walk. On the square, you can see the palace of the same name and the Palazzo Casali, which houses the Museum of the Etruscan Academy.
Montepulciano
Montepulciano is a beautiful and well-known village with around 14 thousand inhabitants in the province of Siena. It is the most popular place in Val d’Orcia, a region known not only for its architectural beauties, history, and monuments but also for its wines and vineyards.
Montepulciano was founded by the Etruscans in the 4th century BC, but the village was developed in the Middle Ages. It has the typical look of the villages of that period, with three walls and an “S” shape.
The busiest place in the village is Piazza Grande, with a beautiful Cathedral built at the end of the 16th century. The church is famous for the heresy trials that were held against Giordano Bruno and Galileo Galilei.
Also worth mentioning, in the same square, is the Palazzo Comunale designed by Michelozzo Michelozzi, the Palazzo Contucci, and the Palazzo Capitano del Popolo, designed by Antonio da Sangallo the Elder.
Furthermore, other monuments that deserve a look are the Pulcinella Clock Tower, located in Piazza Michelozzo, and, outside the village, the Temple of San Biagio. It was built in the 16th century around a 14th-century fresco depicting the Madonna and child.
Pienza
Pienza is another typical charming Tuscan village located less than 10 kilometers (6 miles) from Montepulciano. Contrary to the other villages in this article, it does not have much to do with the Middle Ages. But still, the village has some fascinating history. It was created in the Renaissance period, and nowadays, it represents the triumph of the architectural and urban ideas of that period.
In fact, until the mid-15th century, this village did not even exist. Instead, there was a small village called Corsignano, where was born Enea Silvio Piccolomini in 1405, a member from a noble family who was elected pope with the name of Pius II in 1458.
He decided to give new dignity to the place where he was born, so he founded Pienza. The construction of the village, according to Renaissance principles, was given to the architect Bernardo Rossellino, a former collaborator of Leon Battista Alberti.
His main goal and idea were to bring to earth the “ideal town,” and therefore, Pienza was created from scratch. Nowadays, the village has only 2,000 inhabitants and is considered one of the most beautiful villages in Europe. Even though the whole village is charming, Piazza Pio II really stands out.
The square overlooks the Cathedral, the Palazzo Comunale, and Palazzo Piccolomini, a typical example of Renaissance perfection. Also, the beauty of the square was recognized globally, so today, it is a part of UNESCO as a World Heritage Site.
What are the best small villages in Tuscany
Tuscany is full of small, charming, medieval villages, so it is not easy to decide which ones are the best. In Middle Ages, Tuscany was undoubtedly one of the most important regions in Europe and perhaps in the world, both from an artistic and cultural point of view. This article shows you the most famous Tuscan villages, but there are also many less-known villages that are worth visiting.
Here are some other lovely villages that we recommend: Montalcino, Portoferraio, Monteriggioni, Chiusdino, Vinci, Montecatini Terme, and Poggibonsi. Whichever Tucan village you visit, you will not regret it. They all remained authentic, quiet, and beautiful, and they all are the right place to feel the real Italian dolce vita.
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