We start from Città di Castello along the relaxing Tiber River Cycle Path, accessible only to hikers on foot and by bike. After about 8 kilometres of cycle path, we will take some secondary country roads to reach the magnificent village of Citerna, a medieval town that stands on the green Umbrian hills with its ancient walls, unique for its characteristic architectural structure on two levels: the village, with its narrow streets, monuments, and panoramic viewpoints, and the underground with its underground passageways and cisterns for collecting water used in medieval times. We get back on our bikes and take secondary roads to reach Anghiari, on the famous “straight” road overlooking the valley. We will visit the beautiful village, which has been the scene of important historical events such as the renowned “Battle of Anghiari” painted by Leonardo in 1503. After a well-deserved moment of relaxation with an easy descent, we will return to the Tiber River bike path to reach Citta' di Castello again via traffic-free rural roads.