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Greve in Chianti– Montefioralle – Badia a Passignano – Panzano in Chianti– Lamole – Greve in Chianti
Length: 39.3kms
Estimated riding time: about 2 hours 40 minutes
(19.5 kms bitumen – 19.8 kms dirt road)

This route is graded difficult for its length and the level of fitness and effort required.
As the itinerary doesn’t pass through shaded areas it is advisable to avoid riding during the hottest part of the day in summer.

Km 0 / h 0: Departing from Greve take the road to Montefioralle, a steep climb that will put the rider immediately to the test. (bitumen / uphill)
Km 1.3 / h 10’: Montefioralle is a most charming village from which one can enjoy stunning views overlooking the surrounding vineyards and villas. Originally called Monteficalli for the numerous fig trees growing in the area, the fortified village was situated along a roadway called the Guardingo di Passignano which linked the Val d’Elsa, Val di Pesa , Val di Greve with the upper Valdarno. All that is left of the feudal castle is part of the 13th century wall that forms a semicircle around the S. Stefano church, built in the Gothic style and containing several valuable works of art. In the past this village or “borgo” has belonged to several noble families: Ricasoli, Benci, Buondelmonte and Gherardini. The fame of its wine has been documented since at least 1404.
At the traffic lights continue along the bitumen road. (uphill)
Km 4.6 /h 25’ : Case la Paurosa Turn left at first intersection and then immediately afterwards turn right for Rignana.
A challenging descent.
(bitumen and dirt road / flat and downhill)
Km 6.6 / h 30’ : Take the road on the right.
(dirt / varying terrain)
Km 7.9 / h 34’ : Take the road on the right.
(dirt / downhill, uphill)
Km 9.3 / h 41’ : Badia a Passignano. Situated on a hill the magnificent Badia a Passignano, its crenellated towers and walls flanked by dozens of cypress trees, looks like a castle. It is thought the Abbey was founded by San Zanobi, Bishop of Florence, in 890. It was a place of retreat, penitence and prayer for a group of monks guided by Sichelmo. Two centuries later the monastery adhered to the reform of San Giovanni Gualberto, the founder of the Vallombrosa Abbey who was inspired by the rules of Saint Benedict.
The Abbey witnessed the history and glory of Medicean Florence. In 1810, as a result of the Napoleonic suppression, the monks were forced to leave, the archives and works of art were dispersed and the buildings and farmland were rented. Towards the end of the 1800’s any remaining possessions were auctioned; and crenelated towers and walls were added. However what remains today maintains the great charm of the original edifice: the Corinthian columns at the entrance, the elegant cloister, the courtyards, the frescoes, the refectory, the pulpit sculpted from pietra serena, the enormous kitchen with its huge fireplace and soaring chimney.
Turn right at the first and second intersections.
(dirt / uphill)
Km 12.2 / h 54’ : Case la Paurosa. Turn right, direction Panzano.
(bitumen / varying terrain)
Km 18.3 / h 1.19’ : Panzano dominates a hill situated between the Pesa and Greve valleys. There is written documentation of Panzano castle dating from 1041. Following the disastrous battle of Monteaperti in 1260 the Siena Ghibellines devastated most of the castle walls, fortress and towers. When Siena fell to the Florentines Panzano enjoyed a long period of peace. Riding along the main street of the town one can see the castle’s arched entrance and the mostly reconstructed building that was the ancient feudal residence of the Firidolfi Ricasoli family. Beside the castle is S.Maria Assunta church whose bell tower was one of the castle’s towers. Nothing remains of the medieval church once within the castle’s walls, the artworks of which are now found in the new church. Of note is the renaissance oratory in the Compagnia della SS. Annunziata. A small village began to develop outside the castle walls in the C12th, known today as Panzano Alto.
From Piazza Campana follow the road for Cennatoio-Lamole.
(bitumen, dirt / varying terrain)
Km 19.8 / h 1.26’ : turn right for Cennatoio.
(dirt / uphill, flat)
Km 22.1 / h 1.40’ : Poggio al Sodo. Turn left for Ristoro di Lamole-Agriturismo Le Volpaie.
(dirt / downhill, flat)
Km 23.7 / h 1.47’ : Lamole is situated in a panoramic position. The Romanesque church S. Donato was built in the C13th and restored in the C17th . Riding along the road down to the valley one can see on the left the remains of Lamole castle, today a group of houses.
Take direction for Greve (bitumen / downhill)
Km 27.3 / h 1.53’ : Pile di sotto. Passing a group of houses you will see a little church – take the dirt road on the right and then immediately afterwards take the road to the left.
You will come to the locality Poggio all’ Olmo. Attention! It could be easy to lose your way here…. Ride through the group of houses and take the 3rd road on the right – this path is rough and is situated between a vineyard and a wall. Ahead, after the curve, pass by a path on the right (note a wooden gate). Going ahead, the descent will bring you to a house called Le Lastre. Ride through the olive grove, where the path isn’t noticeable. Once through the olive grove you will see the path again to the right at the beginning of a wood. Ride through the woods – just several hundred metres.
(path, dirt / downhill)
Km 29.3 / h. 2.03’ : Beyond the woods, you will come to another vineyard: take the path to the right. Past the vineyard, pass by the path on the left. Further ahead take the road to the left.
Arriving at Corti di Sopra, ride straight ahead at the intersection (the road to the right leads to Le Corti vineyard). You will ride past several secondary roads.
(dirt / varying ter
rain, downhill)
Km 34.8 / h. 2.27’ : Go straight at the crossroad.
(bitumen / flat)
Km 36.3 / h 2.31’ : Intersection with the SS 222. Turn right.
(bitumen / flat)
Km 39.3 / h 2.39’ : Greve.


Greve in Chianti – Panzano in Chianti – Volpaia - Badia a Montemuro – S. Michele – Greve in Chianti
Length: Km 44
Estimated time: 3 hours
(bitumen Km 18.7 – dirt Km 25.3)

This itinerary is considered difficult for its length and for the quality of the road bed. It is mostly dirt and uphill. It is possible to encounter muddy stretches at Km 31 and Km 32 which could force the rider to walk those patches. Several kilometres of this itinerary form part of the Chianti Extreme bike race.
If you prefer to ride more on bitumen, you could continue on straight from the Badiaccia a Montemuro as far as Torsoli, turn left for S. Michele and then follow directions down to Greve.
Having written of the difficulties, we wish to add the scenery during this itinerary is beautiful, often wild; one rides as far as the southern limit of the Florentine zone of Chianti and to the summit of Monte S. Michele from where the panorama extends for kilometres across the hills. In the woods, before arriving at Badiaccia a Montemuro, you will see Dogole, the long abandoned hamlet and mill. If you wish to stop for a break we recommend the Monte S. Michele woods where the locals often picnic in summer. Near the Villa San Michele complex near the summit there are two restored spring fountains, del Barbiere and del Lavatoio. Villa San Michele has a bar, restaurant and rooms for rent and a hostel. For information: info@villasanmichele.it .

Km 0 / h 0 : Departing from the square in Greve, take the SS 222 (known as “the Chiantigiana”), direction Panzano.
(bitumen / varying terrain)
Km 2.2 / h 8’ : Turn off on the right following the sign for Vitigliano.
(dirt / uphill)
Km 4.2 / h 18’ : Junction with the SS 222 : turn right.
(bitumen / uphill)
Km 5 / h 22’ : Ride past the Piazza di Campana at Panzano. Follow directions for Cennatoio-Montemaggio.
(bitumen, dirt / varying terrain)
Km 6.5 / h 29’ : At junction follow the sign for Cennatoio.
( dirt / varying terrain)
Km 8.8 / h 43’ : Poggio al Sodo. Take the road to the right. 200 metres further on veer to the left, direction Volpaia.
(dirt / flat)
Km 10.5 / h 52’ : Turn to the right, following the CAI 52 track.
(dirt / uphill, downhill)
Km 14.5 / h 1.02’ : Volpaia is a fortified medieval village whose elliptical walls are partly destroyed. The most important building is the Commenda di S. Eufrosino, established in 1443 by bequest of ser Piero della Volpaia. One can see the fortification’s main tower and a smaller tower. The cylindrical tower on the north side is a later addition. When Siena finally fell in 1555, Volpaia was no longer required for defense purposes and it transformed into an agricultural village.
(bitumen / downhill)
Km 18.7 / h 1.13’ : Continue on in the direction for Radda in Chianti. Turn left at the next 2 intersections.
(bitumen / uphill)
Km 21.4 / h 1.27’ : La Villa. Near the Cappella del Mercatale (chapel) go right, following directions for Cavriglia-Lucolena.
(bitumen / downhill, uphill)
Km 26.6 / h 1.55’ : Fattoria di Pian d’Albola. All that remains today of this antique fort is the turret and the village which developed around the castle. In 1551 there were 126 inhabitants here. Today the vineyard is one of the most renowned producers of Chianti Classico. Continue straight on.
(dirt, bitumen / varying terrain)
Km 29 / h 2.08’ : Continue straight on.
(bitumen / varying terrain)
Km 31.1 / h 2.16’ : Badiaccio a Montemuro. Monks of the Camaldoli order founded a monastery here in the
C 11th which united with the Benedictine monastery near Florence in the C 16th. Only a few traces of the monastery remain today.
Approximately 300m further on, on top of a hill look on the left for the CAI 00 track. Turn onto the track and continue straight on, passing by a track on the right.
(bitumen, dirt / uphill)
Km 32.6 / h 2.26’ : Ride straight ahead at first junction. Turn right at next junction; and then continue straight on at the following junction.
(pathway / uphill)
Km 34 / h 2.37’ : San Michele church is built at the top of Mt. San Michele, the highest peak in the Chianti mountain chain. It was built by an order of Vallombroso monks around the year 1000 and was inhabited until 1616. All that is left of the original building are the altar wall and part of the two side walls. Every year, on Ascension Day, lovers celebrate the rite of the “broom knot”, going into the woods where the heavily scented, yellow broom flowers are in bloom and, uniting two of the plants, pledge eternal love.
Continue on, passing several secondary roads on the left.
(dirt / varying terrain)
Km 36.3 / h 2.43’ : Continue straight on at the junction
(dirt, bitumen / downhill)
Km 44 / h 3.00’ : After the pleasant ride down from Monte S. Michele you arrive back in Greve.


in Chianti - Montefioralle - Monte Calvario - Quattro Strade - Mercatale - Ferrone - Poneta - Poggio ai Mandorli - Chiocchio - Nozzole - Passo dei Pecorai - Greve
in Chianti
Length: Km 41.9
Estimated time: about h.2.17'
(bitumen Km 18.5 - dirt Km 23.4)
Rather difficult.

One of the longest itineraries, the unpaved road surface is good and not particularly steep, either uphill or downhill. However, the rider needs to be fit. The itinerary follows the north-west border of Chianti Classico as far as Mercatale. There are two villages along the itinerary: Montefioralle and Mercatale. There aren't many places of cultural interest, but the rider will enjoy the beautiful countryside. En route amongst the hills one will see castles, country churches and farm houses surrounded by vineyards, olive groves and woodlands.
At Km 3.1 the road could be very muddy.

Km 0/ h 0 : departing from Greve, follow directions for Montefioralle. A steep climb
(bitumen / uphill)
Km 1.3 / h 10' : Montefioralle. Do stop and have a stroll through this delightful “borgo”. All that is left of the antique feudal castle is part of the 13th century wall which forms a semicircle around the S. Stefano church, built in the Gothic style and containing several valuable works of art. In the past this village belonged to several noble families: Ricasoli, Benci, Buondelmonte and Gherardini. The fame of its wine has been documented since at least 1404.
Continue straight on riding beside the wall of the village. Turn left near the water fountain.
(bitumen, dirt / varying terrain)
Km 2.2 / h 13' : Turn left at junction, riding downhill
(dirt / downhill)
Km 3.1 / h 19' : Having ridden uphill turn right at junction
(dirt / uphill)
Km 4.4 / h 26' : Keep going straight ahead past the Pernano farmhouse.
(dirt / uphill)
Km 4.5 / h 27' : Turn right along the SP 118, following directions for Mercatale
(bitumen / downhill, uphill)
Km 6.6 / h 37' : Case la Paurosa. Keep going straight on along the bitumen road
(bitumen / uphill)
Km 8.7 / h 44' : Poggio di Testa Lepre. Follow directions for Mercatale
(bitumen / varying terrain)
Km 13.4 / h 52' : Quattro Strade. Go straight on at junction, direction Mercatale
(bitumen, varying terrain)
Km 14.6 / h 55' : Mercatale. During medieval times Mercatale became the market spot for the inhabitants of the surrounding area (they lived in the hills for defence purposes). When peace finally reigned the inhabitants gradually moved close to the market place, the town developed and the hill communities disappeared. During the Renaissance Florentine noble families and merchants built villas in the area.
Follow directions for the town centre and S. Casciano
(bitumen / flat)
Km 16.2 / h 1.00' : At junction turn right for Luiano. There is a wonderful lookout along this road. Do be careful to stay on the right as you ride down the dirt road!
(bitumen, dirt / flat, downhill)
Km 21 / h 1.09' : At junction turn right along the SP 3, direction Greve.
(bitumen / flat)
Km 22.9 / h 1.14' : Ferrone has always been the centre of terracotta production in Tuscany. Production today is mostly paving tiles.
Ride over the stream and turn left near the church, continuing along the dirt road.
(dirt / uphill)
Km 25.9 / h 1.28' : Go straight on at first junction. Turn right at second junction, riding uphill. Ride through the woods, then after approximately 100m turn left and then turn right. Go straight on past several side roads.
(dirt / uphill, flat)
Km 27.1 / h 1.36' : Poggio a Mandorli. Ride past the downhill road on the left. At next junction, turn left.
(dirt / flat)
Km 28.8 / h 1.41' : Chiocchio. Go to the left as you come to the first houses. Continue on to the SS 222 (the "Chiantigiana"). Turn right.
(bitumen / varying terrain)
Km 29.4 / h 1.44' : Chiocchio: Turn right along the dirt road - there is a restaurant ( note: there is a post office further along the street which you turn off). Ride through the wooded area as far as Fattoria di Nozzole. Turn left.
(dirt / varying terrain)
Km 33.6 / h 1.55' : Passo dei Pecorai. Turn left, direction Greve.
(bitumen / flat)
Km 38 / h 2.06' : Turn right at junction, direction Greti-Greve.
(bitumen / flat)
Km 41.9 / h 2.17' : Welcome back to Greve.


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Discovery Chianti
Via I maggio, 32
50022 Greve in Chianti (FI) Italy
Mobile: +39 328 6124658
Skype: discoverychianti
E-mail: info@discoverychianti.com

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