Pianella is a small animated village of passage for those who intend to go from Chianti to Siena and vice versa. The bridge over the Arbia River is the main road junction also for those who want to go to Castelnuovo in the Sienese hills, to Monteaperti in the Crete or to Vagliagli in Chianti.
The GATE is therefore placed in a strategic position for those who intend to travel on foot, on horseback, by bike, motorcycle or car in every direction so much so that even the Eroica route is forced to meet the village twice. The ring starts from Pianella and returns diligently to the village after an unusual and suggestive tour among farms, ancient castles, villas and extraordinary religious buildings.
It is technically challenging and therefore should be taken with a grain of salt, also because of the many dirt roads that are encountered and some sections with significant slopes. You need a gravel bike, a touring bike with wide wheels or a good MTB.
The uncontaminated and «starry» village of Villa a Sesta, with its 4 precious restaurants, and San Gusmé, a characteristic example of a fortified village, invite us to visit and linger, gently stimulating all your five senses. From San Gusmé you don't joke around anymore and you climb up to the 644 meters of the Campi plateau, a place chosen by the Etruscans to see the world at 360 degrees and where, in the Middle Ages, the Sienese built the fortresses of Sesta and Cetamura to defend themselves from the incursions of the Florentine armies.
Going up to Campi is a great undertaking with double digit slopes but what you can see, before and after the stone that indicates the birth of Ombrone, repays every effort. The dirt road leads to the solitary and secluded village of Rosennano, once inhabited only by shepherds and farmers and today chosen by those who love to be surrounded by silence.
The road continues to Montebenichi, an ancient village on a hill that separates Chianti from Valdarno and, after crossing the Ambra River and skirting the Ombrone, reaches an unexpected monument: Abbadia a Monastero.
This is a religious building, first a nunnery and then the seat of the monks of the Abbey of San Salvatore and Fontebuona. The religious left us important maps and news with the Cartulario della Berardenga. Not far away is the castle of Montalto, at whose foot flow precious thermal waters that are still untapped, and the small village of Monastero d'Ombrone, transformed into a luxurious resort.
Rumor has it that Abbadia a Monastero and Monastero d'Ombrone were once connected by an underground tunnel that allowed monks and nuns to visit each other to exchange greetings.
Back on the asphalt road we reach Castelnuovo from Colonna del Grillo passing by the beautiful villa of Sestano, a famous hunting place with a beautiful garden.