Italy is home to countless medieval towns and villages, each steeped in history and bursting with charm. From hilltop villages in Tuscany to coastal gems along the Amalfi Coast, these towns transport visitors back in time, offering a glimpse of life as it was centuries ago. But which are the most beautiful medieval villages in Italy? Here’s our guide to the top 5 must-visit medieval towns in Italy.
Positano, Salerno
Perched on the cliffs of Italy’s iconic Amalfi Coast, Positano is one of the most beautiful villages in Italy. Its medieval roots are visible in the winding streets and terraced buildings that seem to spill into the crystal-clear waters of the Tyrrhenian Sea.
For the best experience, climb to the town’s highest viewpoints to enjoy breathtaking panoramas of the coastline. Stroll through the narrow, cobbled streets, where charming boutiques, cafes, and centuries-old churches await discovery.
Cortona, Arezzo (Tuscany)
Cortona is a medieval town in the province of Arezzo, perched on a hill overlooking the Val di Chiana. With origins dating back to the 5th century BC, this Tuscan village combines Etruscan history with Renaissance charm. Its narrow streets wind past olive groves and historic buildings, including the Palazzo Comunale and the Diocesan Museum, home to an impressive collection of Renaissance art.
Despite its fame from Under the Tuscan Sun, Cortona remains delightfully peaceful and less crowded than other Tuscan towns, making it ideal for travellers seeking authentic medieval Italy.
Matera, Basilicata
Located in southern Italy, Matera is famous for its ancient cave dwellings, the Sassi di Matera, recognised as a UNESCO World Heritage Site since 1993. This medieval town offers visitors a unique journey through history, with rock-hewn churches, underground caverns, and charming winding streets.
Matera’s striking architecture and fascinating historical layers make it a must-visit for anyone exploring Italy’s southern medieval towns.
Volterra, Pisa (Tuscany)
Tucked away in Tuscany near Pisa, Volterra is a medieval town with roots tracing back to the Etruscans. Its ancient city walls, cobbled streets, and medieval towers make it one of Tuscany’s most authentic historical destinations.
Visitors can explore a wealth of museums, ruins, and churches, all perched on a hilltop overlooking the stunning Tuscan landscape. The Roman ruins of Velathri add to Volterra’s unique historical charm.
Pitigliano, Grosseto (Tuscany)
Nestled in southern Tuscany near the Archaeological Park of the City of Tufo, Pitigliano is a medieval village carved almost entirely into the rock. Its warm ochre-coloured buildings and dramatic cliffs create a magical setting that feels frozen in time.
Key landmarks include the Cathedral of Saints Peter and Paul and the Orsini Castle, standing beside a striking medieval aqueduct. Pitigliano’s unique architecture and history make it one of Italy’s most captivating medieval towns.
Discover the most beautiful medieval towns in Italy
Whether you’re exploring the cliffside houses of Positano, the hilltop streets of Cortona, or the rock-cut wonders of Matera and Pitigliano, Italy’s medieval towns offer a timeless journey through history. Each village is a living testament to centuries of culture, architecture, and local tradition, making them must-visit destinations for any traveller.
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