An itinerary through some small towns, generally not well known and touristed (with the exception of Cortona), through a land primarily used for farming and agriculture.
It starts in Lucignano, with its perfectly preserved old town and rare examples of concentric walls of medieval origins again, perfectly preserved. From Lucignano head left towards Monte San Savino, another perfectly preserved old town where you can visit many of the antique shops along the road leading to the countryside. Among these we recommend a visit to "Maria", an antiquarian with a dialect almost incomprehensible (for example, she says 'Erio' instead of 'Euro'!)
Follow the path heading towards Castiglion Fiorentino. In summer you are surrounded by vast expanses of sunflowers that characterise almost the entire Valdichiana. You will see and admire countless Leopoldine, rural buildings constructed by the Grand Duke of Tuscany, Leopold II (hence the name Lepoldine) in the first half of the 19th century. They are the first examples of peasant architecture built on the basis of well-defined projects. These huge buildings had to contain many cattle, with a tower on top suiting the pigeons found in the roof.
Of that culture are still the herds of the 'White Giant', cattle the color of pearl-grey, Chianina, famous for its most divine product: the Florentine steak. Once in Castiglion Fiorentino we recommend a walk in the streets of the historic centre, a perfectly preserved village. Leave Castiglion Fiorentino to head south. After a few kilometres you will find the remains of the castle of Montecchio. A short visit is recommended.
Continue in the direction of Cortona, where we recommend you arrive in the late afternoon. Cortona offers its best near sunset because of its perfect exposure to the setting sun in the west. The ancient stone buildings and walls turn incredible shades of colour as the sunlight touches them before dropping below the horizon. Cortona is also very active culturally - there is a famous summer festival that welcomes distinguished artists from far afield and it is also very proud of its Etruscan origins. For a few hours of the day Cortona can be a bit chaotic as a popular tourist destination so we recommend a visit closer to dusk.