San Galgano, medieval abbey

Best medieval attractions to see in Tuscany

Tuscany is an area full of medieval attractions. During the Middle Ages, this region became very important and was a stop for pilgrims traveling the Via Francigena between Rome and France. It was during this period that different communities were born and the rift between the famous Guelphs and Ghibellines was created, respectively supporters of the Papacy or the Holy Roman Empire. The birth of medieval municipalities such as Florence, Siena, Lucca, Arezzo, and Pisa is due to these two factions.

During the Middle Ages, moreover, the Medici family took advantage of this situation to increase their wealth. Overall emerged Lorenzo de’ Medici, known as Lorenzo Il Magnifico, de facto ruler of the Florentine Republic, and the most powerful and enthusiastic patron of Renaissance culture in Italy. Florentine art and architecture derive in large part from this very family. Lorenzo’s famous descendant, Caterina de’ Medici, married Prince Henry (later King Henry II) of France in 1533.

In 1348, the Black Death epidemic tragically led to the deaths of nearly 70 percent of the Tuscan population. This also inevitably impacted several projects, such as the one related to Siena Cathedral, which remained unfinished precisely because of this event.

Tuscany boasts numerous medieval masterpieces, and in this article, we go over some of the most famous ones:

San Gimignano
Photo: Reiner, Pixabay


We already talked about the Collegiata in San Gimignano in another article (check it out if you want to explore it). It is the majestic cathedral of the city, constructed during the second half of the 11th century, in the Romanesque style.


If you come to visit Siena, you can’t miss seeing the Palazzo Pubblico. Siena’s city hall, a masterpiece of Gothic secular architecture, was constructed at the intersection of the Middle Ages and the Renaissance. It is part of Piazza del Campo, the main square of the city which every year hosts for two times one of the most important horse races around the world, the well-known Palio di Siena.

Photo: Lusia / Pixabay
Photo: Lusia / Pixabay


The abbey was built in 1218. We already tell its history in a different article. Featuring impressively well-preserved walls interspersed with towering arches and circular openings where windows once existed, the remains of the abbey without a roof are presently a captivating spectacle.


The Medieval Castle of Monteriggioni is known as “the gateway to the Middle Ages“, as reported by, and it’s something magical.

The physical structure of this fortified village, established in the 13th century and now a popular stop on the Via Francigena, has changed little and is enclosed by monumental walls with ramparts and 14 watchtowers. Noteworthy sights include the walls themselves and the 13th-century Church of Santa Maria Assunta, while plenty of touristy boutiques offer opportunities for browsing. Additionally, in July, the streets are filled with colorfully clad characters participating in one of Italy’s oldest medieval festivals.


Located in an isolated valley just below the village of Castelnuovo dell’Abate, 11km from Montalcino, is a serenely beautiful Romanesque abbey. According to tradition, the original monastery was founded here by Charlemagne in 781.

The abbey’s church exterior, constructed of pale travertine stone, is simple with the exception of its stone carvings, which include various fantastical animals. Upon entering the church, take note of the capitals of the columns lining the nave, particularly the one that represents Daniel in the lion’s den (second on the right). Beneath it lies an especially intense 13th-century polychrome Madonna and Child, while a haunting 12th-century Crucifixion hangs above the main altar.

Cover Photo: Rudy and Peter Skitterians, Pixabay