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Radda in Chianti to Gaiole in Chianti

· 2 reviews · Hiking route · Radda in Chianti
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  • The Chianti Classico black rooster at a viewpoint in Radda in Chianti
    The Chianti Classico black rooster at a viewpoint in Radda in Chianti
    Photo: Catherine Allan, Macs Adventure
m 550 500 450 400 350 300 14 12 10 8 6 4 2 km
Walk through the quiet Tuscan woods between Radda and Gaiole in Chianti passing the many vineyards and villas of Chianti. 
Distance 14.3 km
4:40 h
365 m
534 m
558 m
358 m

Leave Radda and descend into the valley through shady forests.  Ascend to the church of San Bastiano and traverse the hillside passing villas, and vineyards before reaching the tiny village of Vertine.  Follow the last 2 km of the route on quiet roads between olive groves and vineyards to finish at Church San Sigismondo in the centre of Gaiole in Chianti. 

Please note that the route does pass through undulating terrain between the towns.  

Author’s recommendation

Take your time and explore the shady forests, admire the vistas from the track, and walk around the hilltop village of Vetrine.  Vetrine has been the site of a settlement since 1013 when the Ricasoli family resided in the castle before being thrown out in 1478 by order of Siena.  There are some wonderful views down into the valleys from this village. 
Profile picture of Catherine Allan
Catherine Allan
Update: June 11, 2018
Highest point
558 m
Lowest point
358 m
Best time of year

Track types

Dirt road 0.36%Forested/wild trail 1.12%Road 0.30%Unknown 98.20%
Dirt road
0.1 km
Forested/wild trail
0.2 km
0 km
14 km
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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. 

Please take care on the gravelly/stony tracks and paths, especially after dry conditions, when the dusty terrain can be slippery underfoot.  


Tips and hints

Food & Drink

There isn’t anywhere to eat enroute so make sure you take plenty of water and buy some provisions for the day from Radda in Chianti before setting off.  There is a Co-op supermarket in Radda in Chianti where you can buy provisions for the walk (the location is detailed at 0.2 km in the turn by turn directions).  Once arriving in Gaiole in Chianti there is a choice of restaurants, cafes, and enotecas.  There is also a small supermarket on the main pedestrianised street of Gaiole where you can buy provisions for your walks.  


Some useful links …

The Chianti website is useful if you wish to know a little more about Gaiole’s regional history ( 



Viale Settembre viewpoint, Radda in Chianti (529 m)
43.486481, 11.375155
43°29'11.3"N 11°22'30.6"E
32T 692063 4817580
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Church San Sigismondo on Via Antonio Casabianca in Gaiole in Chianti

Turn-by-turn directions

0.00 km – Start at the viewpoint on Viale Settembre with the large black Chianti rooster (~3 m tall) overlooking the valley and vineyards below.  With your back to the rooster and the view, TURN RIGHT and walk along Viale Settembre with the view on your right and the road on your left. 

0.07 km – BEAR RIGHT onto Viale Febbario to pass the old cinema shortly on your right, and the Carabineri (police station) ahead on your left. 

0.20 km – TURN RIGHT at a pedestrian crossing onto Via del Convento to descend between houses.  [Before turning down the hill the Co-op supermarket is ~100m further on, you may wish to buy snacks or lunch for the walk before returning to this point and continuing the walk.]

0.40 km – Continue STRAIGHT ON, ignore the road on the left, and continue to descend gradually on the road. 

0.55 km – Pass the church and the Casa Chianti Classico museum on your left and BEAR LEFT down the road with the fenced playing field on your right-hand side. 

0.70 km – BEAR LEFT just after the recycling plant buildings on your right-hand side to descend to another split in the road.  BEAR RIGHT onto the gravel track (do not go left into the private property through the green gate). 

0.80 km – Continue STRAIGHT ON at the track junction with the stone building on your right.  In ~100 m pass a further farm house on your right and continue descending into the valley. 

1.00 km – Where the track splits at an old wooden signpost for San Giusto TURN LEFT and descend on the gravel track through the trees.

1.10 km – As the track flattens BEAR RIGHT along the track keeping the stream on your left-hand side. 

1.70 km – Continue STRAIGHT ON and ignore the rough track ascending on the right.

2.10 km – Ascend slightly to join a road opposite a winery sign.  TURN LEFT onto the road, there’s no pavement so beware of cars.  Follow the road for ~700 m.

2.40 km – Continue STRAIGHT ON the road and ignore the road off to the left.  The road soon curves to the right.

2.60 km – Continue STRAIGHT ON (ignore the right turn to Siena) and follow the road as it curves left over a stream and pass the road sign for Commune di Gaiole in Chianti. 

2.80 km – TURN RIGHT sharply and ascend on a minor road following the signpost for San Giusto (0.3 km).  In ~100 m continue STRAIGHT ON the wide gravel track, ignoring the track off to the left. 

3.10 km – TURN LEFT to follow the track passing the church of San Giusto on your right-hand side as the track ascends gently. 

3.20 km – TURN RIGHT and follow the track behind the last building of San Giusto on the right-hand side.  In ~50 m BEAR LEFT onto a rough ascending track.  You will pass on the left of a tree with painted red and white markers – you will see these along the route today. 

3.30 km – Continue STRAIGHT ON and continue ascending on the stony track beneath telephone poles (ignore the track off to the left). 

3.50 km – BEAR LEFT to continue on the main track and follow the red and white markers, ignoring the faint track and clearing on the right. 

3.90 km – Continue STRAIGHT ON at the trees with red and white markers (ignore the ascending track on right).  There is a low stone wall on the right-hand side of the track now. 

4.00 km – Pass a large stone villa on the left-hand side and continue STRAIGHT ON down the tree-lined track.  Continue along the track for ~400 m ignoring any off-shoot tracks.

4.40 km – BEAR RIGHT to stay on the main track and ascend as the track curves right (ignore the faint track straight ahead). Shortly after pass through a wooden gate and walk passed the Le Corta villa buildings on the left-hand side. 

4.60 km – Follow the track and it curves left and continue STRAIGHT ON as the track descends towards a road. 

4.90 km – Meet the road after passing between the stne pillars and metal gates of Le Corta.  Continue STRAIGHT ON across the road to a track and immediately BEAR RIGHT to follow the most defined track through trees.  For ~500 m continue STRAIGHT ON following the track and ignoring any off-shoot tracks. 

5.40 km – BEAR RIGHT downhill on the track and pass a house on the left-hand side.  Continue STRAIGHT ON towards the road. 

5.60 km – At the base of the track TURN LEFT onto the road with vineyards on either side.  There is no pavement so beware of vehicles.  Stay on the road for ~200 m. 

5.80 km – TURN LEFT off the road onto a track and follow the signpost for La Mandria (0.9 km).  Continue STRAIGHT ON ignoring off-shoot tracks and entrance drives to houses. 

6.20 km – At the signpost for Adine BEAR LEFT onto the track descending on the left-hand side of the building. 

6.70 km – Continue STRAIGHT ON passed La Mandria villa on the left-hand side and continue ascending.  Continue STRAIGHT ON to San Bastiano in ~300 m. 

7.00 km – TURN LEFT after passing San Bastiano on the right-hand side and follow the red and white markers on the boulder ahead. 

7.30 km – Pass Lisidor villa on the left-hand side and continue STRAIGHT ON following the red and white markers.  Soon there are rolling vineyards on the left-hand side of the track.

7.90 km – At the edge of the vineyard continue STRAIGHT ON following the track into the trees.

8.20 km – Continue on the main track with exposed bedrock to BEAR RIGHT slightly.  Then BEAR RIGHT again in ~100 m, ignore the faint track on the left.

8.30 km – TURN RIGHT onto a more defined, wider and more even track lined with trees on the left-hand side. Continue to follow the red and white markers. 

8.90 km – Continue STRAIGHT ON passing between the villas and follow the track.  In ~200 m keep to the main track as it curves left and descends to the road in the valley below.  The track meets the road in ~900 m.

9.80 km – TURN LEFT onto the road and follow it for ~300 m.  Please beware of traffic as there is no pavement. 

10.10 km – TURN RIGHT off the road just after crossing a bridge and follow the signpost for Concie (1.2 km) onto the ascending track. 

10.30 km – BEAR RIGHT and follow the signpost for Casuccia and the ceramic studio.  The tracks descends in ~25 m. 

10.50 km – Continue STRAIGHT ON and ignore the split to the right to Casuccia.  The track soon begins to ascend. 

10.70 km – Continue STRAIGHT ON and ignore the track off to the left.  In ~100 m at the edge of the Vigna Casi vineyards BEAR RIGHT and continue on the track with the vineyard fence on the left-hand side. 

10.90 km – At the track junction continue STRAIGHT ON and follow the red and white marker on the wooden post.  Continue for ~400 m with the high fence on the left-hand side as the track descends. 

11.30 km – BEAR LEFT on the track just before the house at Le Conce.  Then BEAR LEFT to go through the wooden gate then TURN RIGHT onto another track and descend towards the stream crossing.  In ~50 m BEAR LEFT up the rough track (with grassy line down the centre) to the red and white painted post on the right.  Ascend on the track as it keeps to the right-hand side of the field. 

11.60 km – TURN LEFT onto a level track which soon begins to ascend and follow the red and white markers on the rocks. 

11.80 km – BEAR LEFT at Villa Chianti Vertine and continue ascending to join the road and the edge of the hilltop village of Vertine. 

12.00 km – At the end of the high stone wall on the left-hand side, at the gates to Castello Vertine BEAR LEFT up the paved/cobbled road.  Continue STRAIGHT ON and pass under two arches.  On passing through the second arch exit the village walls of Vertine.

12.20 km – Leave Vertine and BEAR RIGHT, across from the monument in the trees on your left-hand side, into the car park.  The road soon curves left, continue to follow the red and white markers down the road. 

12.90 km – Continue STRAIGHT ON the road as the track goes off to the right at the signpost for Campino del Paido.  Continue to follow the red and white markers. 

13.40 km – Continue STRAIGHT ON at the road signpost for Gaiole in Chianti. 

13.70 km – Continue STRAIGHT ON passed the first road on the left (Via Alcide de Gasperi) and TURN LEFT at the end of the road onto Via Spaltenna.

13.90 km – Continue STRAIGHT ON across Via Galilei on the right in front of the bell tower, and pass the church building on the left-hand side. 

14.00 km – At the end of Via Spaltenna TURN RIGHT to finish the walk in front of the church on the main street in Gaiole in Chianti (Via Antonio Casabianca).  The street on the other side of the river/drainage channel is pedestrianised – along it you will find plenty of restaurants, a small Coop supermarket and a pharmacy. 


all notes on protected areas


43.486481, 11.375155
43°29'11.3"N 11°22'30.6"E
32T 692063 4817580
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 certain 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. You may wish to use walking poles to help on the ascents and descents, and to provide balance on gravelly terrain.  

Questions and answers

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Dave Pietruszynski
July 22, 2018 · Community
Pastoral views with minimal tarred road travel. Lots of ascents and descents making the hike interesting. Great directions. The vistas were beautiful and being close to vineyards, olive groves, lavender, rosemary, and figs was delightful.
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Karen Burgess
June 02, 2018 · Community
This is marked as moderate but most of it is hard and particularly difficult without any any scheduled stops at all. We found out that there was a lovely cafe at 11.5 km but this was way to late after the long, steep, slippery descents on gravel and rocks and steep rocky climbs in full heat. The walk needs better access to cafes to break and more information about how difficult these climbs are. Often the km indications on the written instructions are very wrong and many of the instructions don’t tell you how hard the climbs are.
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Photos from others

14.3 km
4:40 h
365 m
534 m
Highest point
558 m
Lowest point
358 m
Scenic Linear route Cultural/historical interest


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