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Secluded woodlands, venerable vineyards and ancient churches

From the Chianti to Val di Merse by way of the Montagnola range

Badia a Coltibuono, Gaiole in Chianti
Poggio Tagliato, Municipality of Monticiano
80 km (excluding the 28 km side trip)
13 - 17 hours in 3 o 4 legs
Various rest and drinking stops along the way



We pass through the Chianti, a land of historic, venerable vineyards and rich woodlands where man's presence is barely perceptible. The intimacy of the Montagnola range leads to Val di Merse, one of the most authentic and little-known areas of this land, a veritable paradise for an equestrian holiday.


1° Leg

Distance: 16,5 km
Duration: 2 and a half - 3 hours

This itinerary is a fantastic adventure into the green heart of Terre di Siena. It begins in the highlands of the Chianti, in a place of deep silence: Badia a Coltibuono, just a few kilometres from Gaiole in Chianti. The ancient monastery dating to 1051 is surrounded by a forest of white fir trees. It was home to Benedictine monks from Vallombrosa until 1810, but in the 15th century this abbey of the "Good Harvest" grew considerably thanks to patronage from Lorenzo de' Medici. It is currently a villa and agricultural estate famous for its renowned wine. Its garden displays the design of the ancient hortus conclusus, with geometrical boxwood hedges surrounding beds of aromatic and medicinal herbs. Next to the Badia a monumental Lebanese cedar registered by Tuscany's Corpo Forestale dello Stato and measuring seven metres in diameter soars to a height of twenty metres. The trip begins downhill, leaving behind Badia a Coltibuono and after about 1.5 km crossing the asphalted Strada Provinciale 429, then continuing on toward San Donato Imperano. The road enters the woods below the town, leading toward Gaiole in Chianti. This town fills the valley of Massellone stream and has always been a marketplace and meeting point. Even before the year 1000, the inhabitants of the hill towns would come down to the valley to meet and trade, giving rise to the most important centre in the valley. The town is easily passed to the west, thus reaching the Medieval hamlet of Vertine which marks the northeast edge of the Chianti, bordered by the Monti del Chianti. This natural scenario is dotted with castles. It's worth stopping a moment to admire the Chianti's woods and vineyards from this elevated position. The itinerary then leads toward Strada Provinciale 2: the two run parallel for about 300 metres, then the path turns left and passes over the Piana stream. It now heads toward San Giusto in Salcio, where the dirt road at the bottom of the valley proceeds on to San Fedele. The first leg of the itinerary ends here. At this point the highlands give way to enchanting hills.


2° Leg

Distance: about 13 km
Duration: 2 - 2 and a half hours

We are now in the vicinity of Radda, along the valley of the Pesa river, which silently runs through the great woods of the Chianti. Once in San Fedele, a dirt road passes just to the north of Vagliagli in the midst of ancient farmhouses and then leads to Fonterutoli, passing near the Etruscan necropolis of Castellina in Chianti. The castle of Fonterutoli is famous for one of the most prized and renowned wines in Italy, the Chianti Classico which is produced here. Sooner or later you should give the horses a break and sit down with a goblet of this noble red nectar made mostly from Sangiovese grapes, with a touch of Cabernet Sauvignon. From here the itinerary heads downhill along the course of the Gena stream and reaches the beautiful fortified farmhouse of Campalli, located near the interesting village of San Leonino, which merits a stop in itself. It then continues on toward Podere Giardino and follows the marked route, with stone-covered country roads leading to Podere Sietina. The next destination is Fattoria di Montelupo, which offers a lovely view of the surrounding countryside in addition to a good indication of your position. Having crossed the Gena stream at Podere Canale, the path climbs the hill and leads to the hilltop road just by the fabulous church at Rencine, which really deserves a stop.


3° Leg

Distance: 6,8 km
Duration: just over an hour

The journey continues onward amidst farmland and historical farmhouses. Following the road that travels down into the valley, you encounter Fattoria di Busona. The actual dimension of your leisurely progress becomes evident when after a few switchbacks you pass under the Siena - Florence motorway and then encounter a railroad crossing on the Siena - Empoli line. Above to the right you may admire the breathtaking estate of Stomennano. This stretch of the itinerary concentrates typical aspects of the Tuscan landscape, with alternating woodlands, vineyards, olive groves and wheat fields. From here it is possible to reach the unforgettable village of Monteriggioni by means of the Medieval Francigena road. The village overlooks the entire Elsa valley. In 1213 Siena decided to fortify the town with a massive circuit of walls to protect it from Florentine attack. Its fourteen towers have become renowned, thanks to their description in Canto XXXI of Dante's Inferno (Però che come sulla cerchia tonda/Montereggion di torri si corona/così ('n) la proda che 'l pozzo circonda/torreggiavan di mezza la persona/li orribili giganti...). A ride through vineyards leads to a group of houses in Bracciano, whence a steep climb ends up at the Fattoria di Fioreta, where we reach the road leading to the upper Val D'Elsa.


4° Leg

Distance: 11,5 km
Duration: about 2 hours

At Fattoria di Fioreta, a wide, easy road on the left quickly takes us to a hidden opening in the woods, where a currently unmarked path leads to Podere Casanova in Colle Ciupi. Again in the midst of vineyards, we proceed along the aqueduct, reaching Fungaia and Casagatti. A steep downhill climb leads to Altichiari, a small, lovely hamlet and then to Santa Colomba, a renowned 16th-century villa designed by Baldassarre Peruzzi. Crossing the asphalt road in Santa Colomba (which can be quite slippery) we then pass under the village. Having crossed Strada Provinciale 101 at the bridge over Fosso Arnano, we reach Ripostena by folllowing Fosso Arnano. The itinerary then rises up to Fattoria di Bell'Aria and at Podere Pastine di Sopra leads on toward the abbey at San Leonardo a Lago. The little church is famous for its frescoes by Lippo Vanni and Giovanni di Paolo; it was built in the 12th century atop a hill overlooking the valley which once hosted a lake. It was originally a hermitage, which is open to visitors. The church itself features a simple façade and roof, with a round window above the doorway. The remains of the convent have been transformed into a private home.


5° Leg

Distance: 6 km
Duration: about 1 hour

A straight uphill road leads from San Leonardo al Lago to the Eremo di Lecceto, a fascinating place that has always been consecrated to spirituality in the Agostinian discipline. From the 13th to 19th centuries it was home to Agostinian clerics, subsequently banished by Napoleon. It subsequently housed a closed community of Agostinian nuns. Even St. Catherine revered this place and an ancient manuscript reads: "The solitude in Lecceto was frequently graced by God's servant St. Catherine of Siena, who consulted those wise and holy fathers" (Sacra Leccetana Selva, sec. XVII). The itinerary continues toward the aqueduct and then reaches the farmhouse Pianali. Wooded paths lead downhill to Toiano and then amidst vineyards to Ponte allo Spino, not far from the locality's lovely church. We are now in the vicinity of Sovicille and Val di Merse, where the Montagnola range unfolds in a wide valley. The church, more specifically the Pieve di San Giovanni Battista, is an unmissable stop. It is undoubtedly one of the richest examples of Romanseque architecture in Terra di Siena.


6° Leg

Distance: 9,5 km
Duration: 1 and a half - 2 hours

Once at Ponte allo Spino, it is possible to enter the Fosso Arnano canal, which is walled and paved. Shortly afterward, at the Ponte Grande bridge where the Arnano stream becomes the Rigo, it is necessary to cross the Strada Provinciale 73, which requires some caution (the cars are few but travel at high speeds). We then enter a country road leading to the Linari estate. After crossing the Serpenna stream, we cross the Strada Provinciale di Ampugnano, numbered as 105. Here we take the path that runs parallel to the Serpenna and follow the dirt road to Podere Casa San Francesco. At the crossroads with the municipal road known as Padule we turn left toward the Strada Provinciale called Piano di Rosia, in the vicinity of the village of Stigliano. This area is popular with lovers of equestrian tourism, and just a short distance away lies the hamlet of Bagnaia, where an equestrian competition is held every year.


7° Leg

Distance: 17 km
Duration: 3 - 3 and a half hours

We first cross the asphalt road that connects Rosia to the Siena-Grosseto Strada provinciale 73 and, following a vineyard on the right, we pass behind the Poverina church. At this point we enter the characteristic village of Stigliano and we head toward the Montestigliano estate, crossing the lovely cypress-flanked access roads. At this point the horses can relax a bit while their riders plan a short or long stop to explore the area. Travelling on horseback in this solitary and pristine part of Tuscany is truly unforgettable. You pass through valleys, woods, rivers and silent fields where it is possible to encounter wild boar and deer in their natural habitat. The itinerary then leads down to the village of Brenna, where the Merse river is best crossed dismounted. Once at the Calcinari farmhouse, we turn right and proceed uphill to the panoramic crest path that leads straight to the asphalt road near the La Pineta farm, where we turn right toward Iesa as far as the crossroads for Poggio Tagliato. From here it is possible to take the spectacular circular tour around San Galgano.


8° Leg *

Distance: 16,3 km
Duration: about 3 hours

Riders who are expert or used to relatively long excursions can cover this circuit in a single day. This is a grand little voyage that any traveller on horseback should hope to experience. The trip starts from a midpoint about 8 km down the road from Stigliano to Poggio Tagliato, on a downhill country road that offers a splendid view of the valley of the Merse river. The Alto Merse nature reserve begins at the Mallecchi farm, and the Merse river itself is crossed about 2 km later. Continuing down the municipal road, the rest facility with a shelter and horse accommodation is ideal for a stop or in case of bad weather. Instead, continuing down the dirt road, the trees grow progressively higher and on the right appear the ruins of a Medieval fortification. In summer, this stretch of the river offers some fine swimming. A steep uphill climb leads to the limits of the Riserva Naturale dell'Alta Merse and the La Palazzina farm, where on request assistance and accommodation are available for riders and horses alike. The other alternative is the forest fire access road which offers fantastic panoramas, but can be hot in summer due to the lack of shade. From La Palazzina we move on to the Cerbaiola farm and enter the confines of a nature and hunting reserve. The barrier encountered here may be opened if requested beforehand from the owner. We continue toward the Tabaccaia farm, cross the Feccia river and proceed toward the Statale 73 bis road, which we cross near a service station. Continuing on country trails we reach the hermitage at Montesiepi and the Abbey of San Galgano. At this point we have travelled about 18 Km. The Cistercian Abbey of San Galgano is an icon of great power, the veritable symbol of this land. It is historically and architecturally one of the most important religious structures near Siena and is one of Italy's best examples of the Cistercian gothic style. Arriving there on horseback makes the emotion that much greater. This place commemorates the life of Galgano Guidotti, a young nobleman from Chiusdino who was born in 1148. Against the will of his mother and future bride, he decided to live as a hermit on the hill of Monte Siepi. The cross he worshipped was his sword plunged into the rock. This adventure lasted only a year however, and he died on 3 December 1181 at 33 years of age. He was proclaimed a saint four years later. The miracle of the sword in the rock brings to mind a parallel between St. Galgano's story and the so-called "saga of the Graal" in which the ability to rejoin the pieces of the broken sword were taken as proof of heroism.


9° Leg *

Distance: 12 km
Duration: 2 and a half hours

From San Galgano we proceed by crossing the Merse river and following the marked and equipped trail for a few kilometres, whence we reach the Medieval town of Monticiano. We head for the town's Piazza Sant'Agostino, where Via delle Mura begins. This road offers a lovely view over the valley of the Gonna stream. By then taking the old road from Monticano to Iesa we arrive near the Mulinello agritourism estate, where we proceed along the course of the Gonna stream, following a tributary on the right, and reach the farm Il Canile. Not far away lies the hermitage called Camerata. From here wooded paths and some guidance from the high-tension electrical wires above lead 4.5 kilometres later to the asphalt road near La Pineta-Iesa, in the locality Carrotto, where Le Fontanelle agri-campground is located. The main road on the right leads to the scenic top of Monte Quoio. This asphalt road is quite steep and longer: however, the alternative is longer still and difficult. In Carrotto we again encounter the main Chianti - Montagnola Val di Merse road which continues with the asphalt road on the left for La Pineta. About 2 km later on the left we find the dirt road for Poggio Tagliato (ride around the barrier) which after 3 km leads to the Ferraia farm. Upon turning left we reach the La Ripa farm and then the hamlet of Tocchi, where meals may be had. Castello di Tocchi is a Medieval village dating to 1100. Although it was repeatedly involved in the ongoing conflict between Siena and Florence, it has conserved ancient splendour in its circuit of walls and impressive city gate. From here the view takes in woods of chestnuts, cork oaks, live oaks and hills in the shadow of the summit of Monte Amiata.


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