The tour starts at the foot of the imposing Medici Fortress, the symbol of Volterra’s heavy past. The 14th-century medieval bastion perching on Volterra’s highest hill was used to oppress the rebels of its people against the invasion of Florence. From this perfect viewpoint, you can enjoy a fabulous vista sweeping across the Old Town.

Continue to back forward to the earliest times in Volterra’s history at the Etruscan Acropolis, built on the highest point by Etruscans to best read the signs in the sky. The remains of 7th-century-BC temples offer a precious glimpse into the indigenous Etruscan population.

Right next to the site is the Roman Cistern, the heritage of the second civilization inhabiting the city six centuries later. One fun fact is that it was the setting of the award-winning movie “Sandra - of a Thousand Delights” in 1965.

Proceed to pass by the remains of the Roman Theater, located outside the city walls next to the 13th-century Florentine Gate. The weathered auditorium built on the slopy terrain to take advantage of the natural incline is thought to accommodate 3,500 spectaculars until the end of the 3rd century B.C when it was replaced by thermal baths whose beautiful floors still can be seen.

The next destination is Priori Square. The heart of Volterra surrounded by its most beautiful historic monuments was chosen as a setting for the world-famous “New Moon” movie in 2009. The vibrant square with its bustling arcade cafes, gelato restaurants, and colorful traditional performances is the best spot in Volterra for people-watching and soaking up vibes.

The highlight of the square is the Palace of the Priors or Volterra Town Hall, the oldest municipal building in Tuscany. The 13th-century palace boasting Florence’s coats of arms was built to demonstrate the supremacy of the Florentine government over the power of the bishop, represented by the Cathedral located right behind.

Continue to pass by the Cathedral of Santa Maria Assunta. The present cathedral replaced the original one destroyed by the Florentines during a siege in 1472, triggering their constant conflict. Check out the solemn bas-reliefs depicting the bishop on its eternal wall, testifying their influence in the city, and the tranquil 13th-century Baptistery of San Giovanni Battista right opposite the church.

Finally, visit Etruscan Gate just a stone’s throw away, the most famous entrance of the old city walls built and expanded by many generations. Dating to the 3rd century BC, the three head-shaped statues on its arch have been a long-lasting mystery attracting curious visitors and archaeologists.