The Most Charming Medieval Villages in Tuscany

Written on : 12 March 2021
By : Laura Wendy Harders López

Fancy discovering the ancient side of Tuscany? This beautiful Italian region abounds in well-preserved medieval villages with towering castles and fortresses that bear witness to the splendour of the Middle Ages. Whisk your imagination and travel back in time through cobblestone streets, and explore many monuments and citadels of these beautiful medieval Tuscan villages.

>>> Discover luxury villas in Tuscany

DISCOVER MORE

Rent a luxury villa in Tuscany

Pitigliano

Pitigliano is a medieval village straight out of a fairytale. One can enjoy panoramic views at every angle, as the town was built on a limestone promontory overlooking a large cliff. A wealthy family in the 11th-century known as the Aldobrandeschi built the town's walls. Today, one can admire the beautiful ruins of the castle dell"Aquila, settled in the woods near the river Fiora. Steeped in tradition and culture- Pitigliano village celebrates St. Joseph's Day in a unique reenactment called the Torciata. We highly recommend tasting and appreciate the Bianco di Pitigliano wine, an excellent white wine from Chardonnay and Trebbiano grapes and then stroll along the twisting cobblestone alleyways where one can get lost admiring all of its beautiful corners.

Monteriggioni

Dominated by a beautiful medieval castle built by a Guelph mayor of yore as a fortress, the town of Monteriggioni will instantly capture its visitors' imagination. If you want to admire a village that preserves the purest essence of medieval times, then Monteriggioni is a must-visit. With an almost circular fort built in the 13th-century, this medieval wall has been preserved along with its 14 towers. What also characterizes Monteriggioni are its surrounding breathtaking landscapes, quintessential of Tuscany.

Cortona

Cortona is a renowned medieval village in Tuscany thanks to the film "Under the Tuscan Sun" and its annual festivals. The town's historical roots date back to the Etruscan period during the 5th-century and was one of the first villages where its citizens received Roman citizenship in 89 BC. It features 11th-century Romanesque cathedral houses and numerous medieval masterpieces to contemplate at every corner. Its fascinating architecture, along with its quaint stone cottages, makes for an exciting holiday trip to discover the pure essence of medieval Tuscany.

Collodi

Welcome to the famous town of Pinocchio and Gepetto. Collodi is the town where this story was based. It's a picturesque medieval village encircled by a fortress and has attracted numerous visitors since Pinocchio's storybook was released in 1883. While you're here, don't forget to visit the Villa Garzoni and its magnificent garden, which are the most popular attractions in the village. This small town consists of only 50-cobblestone houses with a beautiful plaza and a quaint Romanesque church. There are only two restaurants, some small stores and wine cellars for the region's wine production.

San Gimignano

San Gimignano is a UNESCO World Heritage Site, home to various historic buildings preserved in keeping with its heritage, allowing visitors' imagination whisked to bygone eras. This medieval village boasts impressively overlooking towers, given the existing rivalry at the time, between the various towns to build the highest buildings. San Gimignano arguably accomplished its first ranking of towering structures, featuring one of the most dazzling skylines in Tuscany. San Gimignano enjoyed a period of highest splendour, and experts maintain that the village in the past boasted 42 impressive towers viewed from miles away. One of the most famous Christian medieval routes, called the Frankish Route, passes through the village. This route was once one of the most transited in medieval times, where believers of the faith would go on a pilgrimage towards Rome.

Volterra

Volterra was one of the Tuscan city-states during the Etruscan era. In the Middle Ages, this village was home to an influential episcopal figure who governed the region. This town bears witness to the splendour of the era, with its magnificent monuments and castle. The Medici fortress and the Palazzo dei Priori are some of the most impressive monuments of the village. The Etruscans settled in Volterra in the 4th-century BC and established a massive encircling defensive wall. Given its defensive hilltop location and forts, the town was able to withstand many attacks.

>>> Discover luxury villas in Tuscany
>>> Explore Tuscany's Breathtaking Countryside depicted in Renaissance Art