The starting point for this particular route is the medieval hilltop town of Montone, a delightful place that has managed to preserve its traditional appeal and character, linked to an historically eventful past. Past Città di Castello, the route winds up into the Umbrian-Marche Apennines, with the rider facing two difficult climbs.The landscape is very beautiful, but the difficulty of the ride means that it is only really suitable for more experienced, fitter riders equipped with a good range of gears, given that sections of the climb up from the town of Apecchio have a gradient of more than 10%.

Starting from Montone’s football ground, a few metres outside of the town walls, turn to your right and ride down towards Città di Castello and Montecastelli, and just past the cemetery to your left, bear right off this secondary road onto an even smaller road which winds down through farmland and woods towards Montecastelli below.At the small roundabout at the bottom of the descent go straight across to the junction with the main SS3bis road: turn right here towards Città di Castello along an almost completely flat section of road.

When you get to the outskirts of the town, turn right towards Pietralunga, and then straight afterwards, bear left at the junction and follow the signs for the hospital. Another kilometre or so further on you come to a set of traffic lights; go straight over the lights, down the hill to the roundabout, and then turn right onto the SS257 Fano road.

A few hundred metres further on, and you are at the beginning of the long, albeit not steep climb (gradient of 6% or less) up to the Bocca Serriola pass. When you get to the top of the pass, which marks the border between the two regions of Umbria and the Marche, carry straight on down the other side towards Apecchio, along the Biscubio Valley. When you get to the town of Apecchio (at km. 45), turn right towards Pietralunga, at which point the wildest, most fascinating, but also the hardest, section of the ride starts. The second climb of the day, in fact, winds up between meadows and thick woodland, and in certain sections the gradient is of more than 10%, which require you to be very fit and to have a good range of gears on your bike. 

This second climb ends at km. 54, but there are another three kilometres or so of undulating road before the descent begins, at km. 57.5. The first kilometre of the descent is very steep and winding, and special care needs to be taken here. At km. 58 turn right back onto the SP201, at which point the descent becomes somewhat gentler, and in 5 kilometres you will be in the medieval town of Pietralunga. From Pietralunga, proceed straight on towards Umbertide: the road continues to winds its way slightly downhill, among the wooded hills, until you get to the foot of the hill leading up to Montone. Then at km. 78.5, turn left off the main road towards Montone, and ride the last three kilometres up to the town, along this shaded, not particularly steep, country lane. Since the central section of this route is always some distance from any nearby town, you should remember to take a puncture repair and emergency tool kit with you when you set out.

The wonderful medieval town of Montone, voted one of the "Most Beautiful Small Towns in Italy", perched on the very top of a steep hill that dominates the surrounding countryside. The most important building in Montone is the fourteenth-century Church of St. Francis, with its polygonal apse and portico. Another interesting construction is St. Catherine’s Convent, which currently houses the Local History Archives, one of the most important documentary sources in the whole of Umbria. Another important church is the Pieve di San Gregorio, the oldest church in Montone, which was built in Romaesque-Byzantine style in around the year 1000. Outside the town, perched on a rocky outcrop, lies the Rocca d’Aries, a massive castle which has been completely renovated fairly recently. Other places of interest include the ancient town of Pietralunga, surrounded by oak woods, and the nearby Candeleto complex, complete with campsite, swimming pool, restaurant and accommodation facilities. The Local Natural History Museum, also situated at Candeleto, has many interesting exhibits, and in particular a substantial ornithological section.