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Gaiole in Chianti Loop Walk via Badia a Coltibuono Monastery

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  • Church San Sigismondo on Via Antonio Casabianca, Gaiole in Chianti
    / Church San Sigismondo on Via Antonio Casabianca, Gaiole in Chianti
    Photo: Macs Adventure
  • / Gaiole in Chianti
    Photo: Macs Adventure
  • / Chianti Classico rooster at ~4.9 km
    Photo: Macs Adventure
  • / Badia Coltibuono abbey
    Photo: Macs Adventure
  • / Roadside villa enroute to Montegrossi
    Photo: Macs Adventure
  • / Montegrossi village signpost ~6.1 km
    Photo: Macs Adventure
  • / Montegrossi village
    Photo: Macs Adventure
m 600 500 400 300 14 12 10 8 6 4 2 km
Ascend to the 11th Century abbey Badia Coltibuono, pass through the tiny village of Montegrossi, and descend on shady forest tracks into the valley of Gaiole.   
Distance 15.5 km
4:00 h
347 m
342 m
652 m
350 m
A steep ascent out of Gaiole in Chianti takes you towards the magnificent Badia Coltibuono abbey, which has spectacular views over the Tuscan countryside from it’s lofty hillside look-out.  From the abbey descend before following the road to Montegrossi passing the Castello di Montegrossi high on the cliffs above the roadside.  Wander through the village of Montegrossi before taking to forest tracks skirting the hillside and eventually descending back into the valley of Gaiole to return to where the walk begins at the church of San Sigismondo. 

Author’s recommendation

If you are interested in the history of Badia Coltibuono it is certainly worth pre-booking a guided tour or wine tasting here (via their website as detailed in tips, hints and links below).  Otherwise the view alone makes the abbey a worthy detour from the walk's loop.  Relax and enjoy the vistas down into valleys on either side of the forest track after leaving the village of Monetgrossi behind. 
Highest point
652 m
Lowest point
350 m
Best time of year

Safety information

The terrain varies from tarred roads, rough tracks, and wide gravel tracks.  On some occasions there is no pavement beside the road so please beware of vehicles (driving on the right-hand side) of the road. 

Tips and hints

 Food & Drink:

There is nowhere to eat along today’s route, unless you have pre-booked a meal at the Badia Coltibuono abbey, so we recommend bringing snacks and a picnic lunch along with plenty of water. There is a shady picnic spot with benches in the village of Montegrossi at around 6 km into the walk.  You can purchase snacks and lunch from the small supermarket on the main pedestrainised street of Gaiole in Chianti.  For you evening meal in Gaiole you can choose from the restaurants, cafes and enotecas in Gaiole's centre.      


A point of interest:

Badia Coltibuono

The name of the abbey means Abbey of the Good Harvest.  It was founded in around 1051, and this is when the first vineyards were planted here.  You can learn more about the abbey’s rich history by pre-booking a guided tour or wine tasting  at


Church San Sigismondo on Via Antonio Casabianca, Gaiole in Chianti (354 m)
43.468524, 11.433037
43°28'06.7"N 11°25'58.9"E
32T 696802 4815721


Church San Sigismondo on Via Antonio Casabianca, Gaiole in Chianti

Turn-by-turn directions

0.00 km – With your back to the church of Gaiole in Chianti (where Via Spaltenna joins Via Antonio Casabianca).  TURN LEFT and follow the main street to cross a stone bridge with metal railings in 80 m.  Immediately over the bridge TURN RIGHT then TURN LEFT onto Via Baccio Bandinelli da Gaiole (with butcher on left-hand side on the corner).  Look out for the red and white painted markers on the lamppost ahead. 

0.15 km – BEAR RIGHT as Via Baccio Bandinelli da Gaiole curves right.  Note the red and white markers on lamppost on the right.  There are metal railings on the right-hand side. 

0.25 km – At the T-junction TURN LEFT follow brown road sign post for Riecine.  Continue uphill on the tarred road for ~1 km. 

1.20 km – Continue on the road as it becomes a wide gravel track and curves left passed the entrance to Riecine winery on the left-hand side in ~50 m.  Stay on the main track and ignore and off-shoots. 

1.50 km – Continue STRAIGHT ON passed another entrance to Riecine on the left-hand side. 

1.70 km – A track joins from left, ignore it and continue STRAIGHT ON following the red and white markers on tree trunks and rocks. 

2.00 km – At a large red brick building on the right-hand side of the track there a traffic lights for traffic along the next narrow section of the road.  There is no pavement here so beware of any vehicles along this narrower section of track.  Continue STRAIGHT ON main track for ~1.5 km and ignore any off-shoots.

3.30 km – Where the track joins the road TURN RIGHT onto the road.  Beware of traffic on the road as there’s no pavement. 

3.40 km – TURN LEFT off the main road signposted for Badia Coltibuono.  The Chianti black rooster is on your right-hand side.  Continue to follow the road uphill to the village. 

3.50 km – TURN RIGHT as the road splits and follow the road signposted for Badia Coltibuono (1 km).

4.20 km – Arrive at Badia Coltibuono.  You can take pre-booked guided tours of the abbey or have a pre-booked wine tasting.  After having a look around return to this spot to retrace your steps down the hill. 

4.90 km – At the fork in the road BEAR LEFT with the black rooster on your left-hand side then in ~50 m continue STRAIGHT ON at cross-roads signposted for Montegrossi (1.3 km) and ascend on the road.

5.60 km – Pass the industrial quarry buildings on the right-hand side and continue STRAIGHT ON

5.80 km – Look up to see Castello di Montegrossi high above the the cliffs on the left-hand side and continue STRAIGHT ON

6.10 km – Continue STRAIGHT ON passing the Montegrossi signpost on the right-hand side.  Follow the road as it descends into Montegrossi and curves right through the village. 

6.40 km – Continue STRAIGHT ON as the tar road through the village turns into a track at the last building on the left-hand side. 

6.50 km – Continue STRAIGHT ON ignoring the track off to the left and follow the signpost foe Montelucci.  In ~ 50 m continue STRAIGHT ON at another signpost for Montelucci.

6.70 km – BEAR LEFT to follow the red and white markers on tree and pass onto Via del Rominorio.  Montelucci is up on the right. 

7.30 km – Continue STRAIGHT ON ignoring the track off to the left. 

8.20 km – BEAR LEFT keeping to the main track as a smaller track goes off to the right. 

8.60 km – At the T-junction TURN RIGHT onto another track to follow the red and white markers and the signpost for Ensoli (1.1 km).

9.10 km – TURN RIGHT onto the track to follow the red and white marker on the tree.  In ~50 m continue STRAIGHT ON ignoring a track off to the right.

9.60 km – Where the track slits (signpost to Ensoli on left) BEAR RIGHT to descend on the track. 

10.10 km – Continue STRAIGHT ON as a track joins from the left. 

10.50 km – Continue STRAIGHT ON as bedrock track ascends on the right.  Follow the red and white markers as the track descends and begins to zig-zag down the hill.

11.20 km – At the T-junction TURN RIGHT sharply and continue on the track.

12.50 km – On reaching a fence at the edge of the vineyard follow the track as it takes a sharp bend.  The hilltop village ahead is Barbischio. 

12.80 km – TURN LEFT to follow the main track beneath telephone poles. 

13.50 km – After passing a grassy open space on the left-hand side continue to the end of the track.  Continue STRAIGHT ON where the track meets the road, there is no pavement so beware of vehicles.  Follow the red and white markers beside the road for ~2 km into Gaiole in Chianti. 

14.80 km – At the cross roads continue STRAIGHT ON Via g. Maconi, there is a pavement on the left-hand side of the road. 

14.90 km – Pass the police station (Carabineri) on the left and continue STRAIGHT ON through the car park aiming for the large metal rooster ahead. 

15.00 km – At the large metal rooster TURN RIGHT and follow road signpost for Montevarchi.  Continue STRAIGHT ON until reaching the church steps where the walk began.

15.30 km – The walk finishes at the steps of the church in Gaiole in Chianti.  The pedestrianised street on the other side of the river had plenty of restaurants, cafes, some shops, and a gelateria where you can get some refreshments before heading back to the accommodation. 


all notes on protected areas


43.468524, 11.433037
43°28'06.7"N 11°25'58.9"E
32T 696802 4815721
Arrival by train, car, foot or bike


This depends on the time of year you are walking; if travelling in the spring or autumn it can be cool in the morning but it soon heats up in the late morning and afternoon so make sure and bring some layers with you.  During the summer months the area can be prone to afternoon thunderstorms so waterproofs are also essential in case of heavy showers.  In the heat of the day suncream is essential and a sunhat is highly recommended.  Otherwise normal hiking gear in a ~25 litre rucksack will suit.  Either sturdy walking shoes, or light hiking boots are suitable. 

Basic Equipment for Hiking

  • Sturdy, comfortable and waterproof hiking boots or approach shoes
  • Layered, moisture wicking clothing
  • Hiking socks  
  • Rucksack (with rain cover)
  • Protection against sun, rain and wind (hat, sunscreen, water- and windproof jacket and suitable legwear)
  • Sunglasses
  • Hiking poles
  • Ample supply of drinking water and snacks
  • First aid kit
  • Kit para bolhas
  • Bivy / survival bag  
  • Survival blanket
  • Headlamp
  • Pocket knife
  • Whistle
  • Cell phone
  • Cash
  • Navigation equipment / map and compass
  • Emergency contact details
  • ID
  • The 'basic' and 'technical' equipment lists are generated based on the selected activity. They are not exhaustive and only serve as suggestions for what you should consider packing.
  • For your safety, you should carefully read all instructions on how to properly use and maintain your equipment.
  • Please ensure that the equipment you bring complies with local laws and does not include restricted items.

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Dave Pietruszynski
July 23, 2018 · Community
The threat of thunderstorms caused us to start early and we reached Badia Coltibuono around 10:30am well before the first wine tour at 2:30pm. The early morning shade on the steep ascent was welcome in the heat. The rest of the hike is along the ridge line and was easy. Once again great views and directions. The fragrance of the blooming lavender along the hike was special. 10 miles with no other hikers... a few cars and trucks (less than ten) on the limited paved roads. Gaiole is a sleepy town - enjoyed observing the rhythm of a small Italian village. Nice interaction with the restaurant, hotel, and shop vendors.
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View of Gaiole just before reaching Montegrossi
Photo: Dave Pietruszynski, Community

Photos from others

View of Gaiole just before reaching Montegrossi

15.5 km
4:00 h
347 m
342 m
Highest point
652 m
Lowest point
350 m
Circular route Scenic Healthy climate


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