Montefioralle: A Medieval Marvel

Nestled just a stone’s throw away from Greve in Chianti, Montefioralle is a medieval gem that seems frozen in time. Encircled by ancient walls, this small village boasts cobblestone streets, stone houses adorned with colorful flowers, and a castle that dates back to the 11th century. Montefioralle offers a tranquil escape from the bustling tourist spots while providing a glimpse into Tuscany’s rich history.

Pienza: The Ideal Renaissance Town

While not entirely undiscovered, Pienza often takes a backseat to more renowned Tuscan towns. This UNESCO World Heritage site, envisioned by Pope Pius II, showcases a harmonious blend of Renaissance architecture and urban planning. Visitors can wander through Pienza’s charming streets, admire the panoramic views of the Val d’Orcia, and indulge in the town’s renowned pecorino cheese—a local delicacy.

Bolgheri: A Wine Lover’s Paradise

Nestled among cypress-lined roads and vineyards, Bolgheri is a tiny village in the Maremma region that has earned a reputation for its excellent wines. The picturesque landscape, complemented by the medieval charm of the village, creates an enchanting atmosphere. Bolgheri’s wine route, known as the “Strada del Vino,” offers a delightful journey through local vineyards and wineries, making it a must-visit for wine enthusiasts seeking an authentic Tuscan experience.

Certaldo Alto: A Medieval Citadel

Overlooking the Val d’Elsa, Certaldo Alto is the medieval counterpart to the modern town of Certaldo. Linked by a funicular, this well-preserved citadel invites visitors to stroll through narrow cobblestone streets and admire medieval architecture. With its medieval towers, charming squares, and a sense of tranquility, Certaldo Alto is a hidden treasure that transports visitors back in time.

Anghiari: An Artistic Oasis

Situated in the eastern part of Tuscany, Anghiari is a village that boasts not only medieval allure but also a rich artistic heritage. Known for the Battle of Anghiari, famously depicted in a mural by Leonardo da Vinci (though the mural itself is lost), the village exudes a sense of history. Visitors can explore the winding streets, discover local artisan workshops, and appreciate the art that permeates the atmosphere.

Castiglione d’Orcia: Amidst Cypress Trees and Thermal Springs

Nestled in the Val d’Orcia, Castiglione d’Orcia is a village that seems to emerge from a Tuscan postcard. Surrounded by cypress trees, olive groves, and thermal springs, the village offers a serene escape. The Rocca di Tentennano, a medieval fortress, dominates the skyline, while the town’s streets provide a quiet retreat for those seeking the beauty of Tuscany without the crowds.

Lucignano: A Jewel in the Val di Chiana

Lucignano, perched on a hill in the Val di Chiana, is a village celebrated for its unique elliptical layout. Encircled by medieval walls, the town’s concentric streets lead to the central Piazza del Tribunale. Lucignano’s charm lies in its well-preserved medieval architecture, including the Collegiate Church of San Michele, and its ability to offer a tranquil escape off the beaten path.

Suvereto: A Medieval Hilltop Haven

Situated near the Tuscan coast, Suvereto is a medieval hilltop village that boasts a well-preserved historical center. The village exudes a quiet elegance with its medieval walls, narrow alleys, and ancient churches. Suvereto also takes pride in its local wines and olive oils, making it an ideal destination for those seeking a taste of authentic Tuscan flavors away from the tourist crowds.

Monteriggioni: A Fairytale Fortress

While Monteriggioni is not entirely unknown, its fairy-tale appearance often goes underrated. This small walled town is characterized by its perfectly preserved circular walls and watchtowers. Monteriggioni offers a glimpse into medieval Tuscany, and visitors can climb the walls for panoramic views of the surrounding countryside. Despite its proximity to popular destinations like Siena, Monteriggioni maintains a peaceful atmosphere.

Tuscany’s allure extends far beyond its famous cities, and these underrated villages embody the essence of the region. Stepping into these hidden gems allows travelers to escape the crowds and immerse themselves in the authentic charm of medieval Italy. From the vineyards of Bolgheri to the medieval streets of Certaldo Alto, each village on this list invites exploration, promising a unique and intimate experience that captures the timeless beauty of Tuscany. So, for those seeking the road less traveled, these hidden treasures offer a chance to discover the true soul of this enchanting region.