We set off from Città di Castello along the relaxing Tiber River Bike Path, accessible only to hikers and cyclists. After about 8 kilometres on the bike 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 distinctive two-level architectural structure: the village, with its narrow streets, monuments, and vantage points, and the underground level with its subterranean 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 that overlooks the valley. We will visit the beautiful village that was the scene of important historical events, such as the famous “Battle of Anghiari” painted by Leonardo in 1503. After a well-deserved moment of relaxation with a leisurely descent, we will rejoin the Tiber River cycle path to return to Città di Castello along traffic-free rural roads.