The Most Charming Medieval Towns to Explore in Tuscany

Exploring the medieval towns of Tuscany is like stepping into the pages of a historical novel. These well-preserved towns provide a unique experience, perfect for one-day activities during your stay.

volterra view

Are you ready to embark on a journey back in time to ancient Italy? Exploring the medieval towns of Tuscany is like stepping into the pages of a historical novel. These well-preserved towns provide a unique experience, perfect for one-day activities during your stay. In this article, we will guide you through some of the most enchanting medieval towns in Tuscany, highlighting the historical sites that make this region an essential destination for any traveler.

Medieval Towns in Tuscany to Visit

Beyond its crystal-clear sea, culinary excellence, and vibrant art cities, Tuscany is rich with ancient roots dating back to Etruscan settlements and other significant civilizations. The region is dotted with towns that have preserved their medieval charm, each narrating a unique story of art, architecture, and culture. Whether you're a history buff, an art lover, or a wine enthusiast, Tuscany promises an unforgettable journey through time.

Volterra

Volterra is the oldest town in Tuscany - a treasure trove of history, perched on a hill with stunning views over the countryside. Known for its Etruscan origins, when it was one of the  city-states, and Roman theater, Volterra's medieval walls, the Medici fortress and Palazzo dei Priori reflect its rich past. Don't miss the alabaster workshops, a craft deeply rooted in the town's heritage.

San Gimignano

San Gimignano, often referred to as the "Medieval Manhattan," is an UNESCO World Heritage Site famous for its towering medieval structures. Its 14 towers, out of the original 72, dominate the skyline, offering a glimpse into the town's prosperous past. Wander through Piazza della Cisterna and explore the Collegiata, a cathedral adorned with frescoes.

Monteriggioni

Monteriggioni is a perfectly preserved medieval fortress, offering a unique glimpse into the past. Encircled by complete walls and 14 towers, this town showcases exemplary medieval military architecture. Visitors can enjoy panoramic views from the walls and explore the Piazza Roma at the town's heart. Dominated by a stunning medieval castle, Monteriggioni captures the essence of medieval times, set against the breathtaking landscapes of Tuscany.

Radda in Chianti

Nestled in the heart of the Chianti wine region, Radda in Chianti is surrounded by vineyards and olive groves. This charming town features medieval walls, narrow streets, and the Palazzo del Podestà. It's an ideal spot for wine enthusiasts to explore the local Chianti Classico.

Cortona

Cortona, the picturesque setting of the movie “Under the Tuscan Sun,” is perched on a hilltop, offering breathtaking views of the Val di Chiana. With roots dating back to the 5th century Etruscans and medieval landmarks like the Palazzo Comunale and the Romanesque Santa Margherita Basilica, Cortona is a captivating destination. The town’s enchanting architecture, combined with its charming stone cottages, provides a perfect backdrop for a holiday that captures the pure essence of medieval Tuscany.

Collodi

Collodi, the birthplace of Pinocchio's author Carlo Collodi, is a gem worth visiting for its distinctive charm and historical importance. This quaint town features the delightful Pinocchio Park, a tribute to the beloved story, and the elegant Villa Garzoni with its breathtaking gardens. Despite its small size, consisting of just 50 cobblestone houses, Collodi boasts a beautiful plaza and a charming Romanesque church. Visitors can enjoy the local flavor at the two restaurants, browse the small stores, and explore wine cellars showcasing the region's wine production.

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