Pitigliano, perched atop a volcanic tuff cliff, is often called “Little Jerusalem” for its rich Jewish heritage. Intertwined with rock and history, this enchanting town offers a captivating day trip for those eager to explore Southern Tuscany’s hidden gems.

Begin your journey by strolling through the ancient streets, where Etruscan roots run deep. The Vie Cave, narrow pathways carved into the tuff rock by the Etruscans, offer a glimpse into the past. These ancient roads, with towering walls over 65 feet high, connected settlements and necropolises, showcasing the impressive ingenuity of the Etruscan civilization.

Wander through the Jewish quarter, known as “Little Jerusalem.” Pitigliano became a refuge for Jews fleeing the Papal States in the 16th century. The Synagogue, built in 1598, is a testament to this vibrant community. Visit the Jewish Museum, the Mikveh (ritual bath), the kosher butcher shop, and the Forno delle Azzime (unleavened bread bakery) to experience the daily life of the Jewish residents.

Next, explore the grand Palazzo Orsini, a fortress-turned-palace that dominates the main square. Initially built in the 11th century, the Aldobrandeschi family transformed it, and later, the Orsini family transformed it. Today, it houses the Diocesan Museum and the Archaeological Museum, which display Etruscan artefacts and sacred art, including works by Jacopo Della Quercia.

Marvel at the Medici Aqueduct and the Fontana delle Sette Cannelle. The 16th-century aqueduct brought water to the town and ended at the elegant fountain adorned with sculpted animal heads. This engineering marvel, designed by Antonio da Sangallo the Younger, reflects the Medici family’s influence on Pitigliano.

A short walk from Palazzo Orsini leads to the Duomo di Pitigliano, the Cathedral of Saints Peter and Paul. This 13th-century church, with its Baroque façade, houses the stunning Madonna of the Rosary with Saints by Francesco Vanni. The single nave interior offers a serene space for reflecting and admiring its artistic treasures.

Take advantage of the breathtaking views from Via San Michele. This scenic viewpoint offers a perfect panorama of Pitigliano’s cliffside setting. Relax on shaded benches and soak in the picturesque landscape, or enjoy a meal at a nearby terrace restaurant, where the views are as impressive as the friendly service.

For an adventurous twist, explore Pitigliano’s underground tunnels and caves. These ancient structures, dating back to 400 AD, include a Christian cave chapel, the oldest in Italy. Occasionally open to the public, these tunnels reveal the town’s hidden depths and historical layers.

Pitigliano’s blend of Etruscan heritage, Jewish history, and Renaissance elegance creates a unique tapestry that captivates visitors. Whether wandering through its ancient streets, savouring local delicacies, or marvelling at its architectural wonders, a day trip to Pitigliano promises an unforgettable journey through time and culture. Embrace the magic of this Tuscan treasure and let its stories unfold before you.