The starting point of our Hiking throughout Sienese Chianti Castles is Gaiole in Chianti, an ancient market place located in the valley of the Massellone stream, forty minutes from Siena. The first kilometres of our journey is one of the most difficult stretches of the entire route, since we will have to face 320 metres of altitude difference over a distance of 5 kilometres. Going towards Montegrossi, one of the oldest castles in the whole area of which today only one tower remains, you will be surprised by the dizzying view of an ancient stone quarry that is located on the way. Valdarno, which now, after the many curves and gorges you have faced – even if only to reach the starting point of the trek – you can see that it opens up in all its grandeur, crowned by the majestic Pratomagno.rosan monastery has existed here for centuries is tangible thanks to the fir still present in an important extension, mixed with the oaks that show themselves with a much more varied colours than conifers, thanks also to lichens.We will then descend quickly to cross only the asphalt for one point – it is the road to Radda – and then continue along the CAI path.Continuing with our Hiking throughout Sienese Chianti Castles, suddenly the fortified village of Vertine will appear in front of you behind a curve.

Once back in the village, it may be time for an aperitivo enjoying the fresh evening air, when the sun has already set behind the mountains and even the last blushes of the sky have faded. A drink is possible in one of the historic cafes of the place, with a characteristic country style that is due to the celebration of the Eroica, a very famous historic cycling competitions.

The day is drawing to a close and the memory that you will take home, once you feel your legs heavy when you get into the car, is the unknown story of a Chianti that is not that of its cellars but that of castles and knights who competed for the control of this middle earth.