Starting from Piazza Mazzini the trail goes towards the river Tiber then follows a dirt road up the valley towards Montone. It follows the Tiber for about three kilometres before turning inland at km 5.5 to the main road between Montone and Umbertide. From here, it turns left, then right at km 5.8 along a country lane to San Lorenzo. At km 6.2, it leaves the paved road and goes along a dirt track in the middle of the fields where there is a good view of Montone to the left. 

At km 10, after a short climb, it goes along a paved lane which returns to the main road (km 11.5) after a short descent. After crossing the road (beware of traffic), it enters another dirt road and climbs towards Montone: this is the most difficult part of the trail, because the last few metres are very steep and will force less experienced cyclists to dismount.

Back on the paved road (km 12.3), the climb is gentler, and in less than a kilometre the trail reaches Montone, where the beautiful historic centre and views over the valleys below make a visit well worthwhile. From here the trail descends towards Umbertide, meeting the dirt road again at km 18.7 after turning right at a bend to the left.

From here, the trail returns to the Tiber (km 23) through a labyrinth of paved and unpaved lanes through flat countryside. It then follows the first part of the route back to Piazza Mazzini, which is close to the Rocca and the town centre.

As well as the historic centre of Umbertide with its superb medieval Rocca, already mentioned in Trail no. 4, a visit to the walled village of Montone is a must. The church of San Francesco (14th century), which has a polygonal apse and a single nave, is the most important building in the town. In the historic centre is also the former convent of Santa Caterina, now hosting the town’s historical archives (archivio Storico Comunale), among the most important in Umbria for their rich heritage of documents. Another important religious building is the pieve of San Gregorio, the oldest church in Montone, constructed in Romanesque-Byzantine style in about AD 1000. Just outside Montone is the Rocca d’Aries, an imposing castle that has recently been restored. Not far from Umbertide is the Civitella Ranieri castle, also worth a visit. The natural scenery around the river Tiber and the wood-covered hills are also beautiful to see.