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San Sano Loop Walk

· 1 review · Hiking route · Gaiole in Chianti
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  • The road descending out of San Sano
    The road descending out of San Sano
    Photo: Catherine Allan, Macs Adventure
m 450 400 350 300 250 200 12 10 8 6 4 2 km
From San Sano roam through the old woodlands of Dievole, revel in the natural surroundings, and leave the Natural Park via tracks passed beautiful villas and olive groves before returning to San Sano. 
Distance 13.3 km
4:45 h
364 m
368 m
446 m
264 m
Like a good Chianti wine this walk improves as time passes; begin on the road descending from San Sano, join a wide track, soon you'll reach the shady woodland tracks and paths through the natural park.  Pass by stunning villas and enjoy excellent views over the Dievole woodlands, vineyards, and olive groves.  Finish the route by walking through the tiny, but beautiful, hamlet of Tosa to join a quiet road into San Sano.

Author’s recommendation

Keep an eye out for wildlife as you walk through the old forests for the Dievole Natural Park.  There’s a good chance you could spot deer, squirrel, foxes, varied bird life, and perhaps even a wild boar out during the day (the latter are largely nocturnal animals). 
Profile picture of Catherine Allan
Catherine Allan
Update: July 25, 2018
Highest point
446 m
Lowest point
264 m
Best time of year

Track types

Dirt road 0.06%Road 3.02%Unknown 96.91%
Dirt road
0 km
0.4 km
12.9 km
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Safety information

At the end of the walk after Molino del Lupo there is a stream crossing (~2 m wide) there are stepping stones/rocks in the stream to help you cross safely, however if there has been a lot of rain recently it may not be passable.  The crossing is 11.2 km into the walk.  Poles are highly recommended for the stream crossing to help with balance.  


The terrain varies from tarred roads, rough tracks, wide gravel tracks, narrow dirt paths, and grassy woodland 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:

Make sure to take plenty of water, snacks and lunch with you on today’s route as there’s nowhere to eat along the route until 9.4 km when you reach Dievole Villa.  It is only open for meals seasonally so make sure to check the opening times and book if you would like to eat lunch there.  Otherwise, there is a good trattoria in the village of San Sano to eat when the Hotel San Sano restaurant isn’t open during the off-peak season.  Next to the trattoria is a small grocery shop where you can buy fruit and sandwiches for picnic lunches. 


Some points of interest:

San Sano Trattoria (please note this is closed on a Wednesday but the hotel can provide dinner if this is the case): 

Dievole Villa: 


Frog fountain in the centre of San Sano (389 m)
43.422125, 11.389219
43°25'19.7"N 11°23'21.2"E
32T 693406 4810465
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Frog Fountain in the centre of San Sano

Turn-by-turn directions

0.00 km – Facing the frog fountain in the centre of San Sano village.  TURN LEFT and follow the road ascending slightly out of the village.  The road soon passes between vineyards. 

0.50 km – At the large pine tree on the left-hand side of the road continue STRAIGHT ON and follow the road.

0.70 km – At the Marchesi Antinori buildings on the right-hand side of the road continue STRAIGHT ON and follow the road as it becomes tree-lined. 

1.90 km – TURN RIGHT off the road onto the track which descends at the Parco Scultare (2.8 km) signpost.  Follow the track as it curves to the right.

2.80 km – Continue on the main track and TURN LEFT to cross the wide bridge. 

2.90 km – After curving right on the track TURN RIGHT off the main track to follow the Dievole Natural Park signpost.  Then TURN LEFT at the next signpost in ~20 m to walk along with a vineyard on the left-hand side. 

3.50 km – BEAR LEFT keeping the fence on the left=hand side and follow the fence to a track ahead.  On reaching the track in 100 m TURN RIGHT onto it, then in ~20 m TURN LEFT off the main track following the “Divieto di Transito” signpost.  Ascend on this track as it curves right.

3.80 km – Where the track splits continue STRAIGHT ON ascending with Dievole 7 signpost on the left-hand side.

3.90 km – As the track meets a wider track on a bend continue STRAIGHT ON to the track as it curves right to continue ascending. 

4.10 km – Opposite the Dievole signpost TURN RIGHT into a vineyard across a narrow cattle-grid with vines on the right-hand side. 

4.30 km – BEAR LEFT keeping the fence on your left-hand side and continue ascending as another track descends on the right.  In ~50 m continue to narrow cattle-grid straight ahead.  Once over the cattle-grid TURN RIGHT onto a track through trees. 

4.40 km – TURN RIGHT onto a grassy track signposted for Dievole (with red arrows on signposts also) and walk along a lovely grassy track through old woodland for ~600 m. 

5.00 km – At a track crossroads continue STRAIGHT ON the level track ahead. 

5.30 km – Follow the track as it curves sharply to the left and continue STRAIGHT ON the track. 

5.40 km – At the signpost with red arrows on the track bend TURN LEFT and ascend on the track. 

5.80 km – Continue STRAIGHT ON ascending as a faint track crosses the path.

5.90 km – On reaching the gate into the vineyard TURN RIGHT to cross the cattle-grid then TURN RIGHT into the vineyard.

6.00 km – Continue STRAIGHT ON over the cattle-grid ahead (the vines are on the left-hand side) then continue to follow the gravel track, ignoring any off-shoot tracks and paths for ~600 m. 

6.60 km – After the track curves left and reaches a gravelly clearing BEAR RIGHT onto a small track hidden behind a small dirt embankment with Dievole signposts next to it.  TURN RIGHT and follow the path as it descends through the trees.  In ~100 m keep left of the red painted signposts. 

6.90 km – At the signpost with the red arrow on it BEAR LEFT on the more defined track and continue descending to a fence.

7.00 km – At the gate into the vineyard TURN LEFT and coss the cattle-grid then TURN LEFT into the vineyard and follow the track with the vines on the right-hand side.

7.20 km – At the other end of the vineyard TURN RIGHT to cross the cattle-grid then continue STRAIGHT ON to ascend slightly on the track.

7.60 km – Just after a stream crosses the path TURN LEFT onto a grassy track with Dievole signpost on the right-hand side. 

7.80 km – As a track joins from the right TURN LEFT onto a track with signpost for Villa Dievole on the right-hand side then continue STRAIGHT ON.  In ~50 m as a track goes off on the right-hand side cross the stream to ascend. 

7.90 km – Continue STRAIGHT ON the track as another track joins from the left. 

8.20 km – As the path slpits BEAR RIGHT onto a narrow path through the trees with a red arrow signpost on the left-hand side.  The path begins to descend with wooden railing on the right-hand side. 

8.30 km – Stay on the path as it curves sharply to the right crossing a stream channel over the path and continue STRAIGHT ON the path. 

8.40 km – Where the track splits BEAR RIGHT and descend on the grassy track (red arrow signpost on the left-hand side). 

8.50 km – In the grassy clearing BEAR LEFT up the dirt track towards a boulder and benches on the right-hand side.  There is also an information board in the upper clearing on the left-hand side.  After passing the boulder opposite the information board TURN RIGHT onto a track through the trees. 

8.60 km – BEAR LEFT with red arrow signpost on the right-hand side to continue ascending on the dirt track.

8.70 km – TURN RIGHT to follow the track uphill ignoring a faint track ahead.

8.90 km – Ascend to the side of a wide tree-lined track but TURN RIGHT onto the smaller track in front of it and walk towards the telegraph pole in ~50 m then BEAR LEFT before the telegraph pole to walk on the right-hand side of the wide track below.  (Pass the gymnasts rings on the right-hand side.)

9.10 km – BEAR LEFT of the building and descend onto the wide track.  TURN RIGHT onto the track and follow it for ~500 m.

[9.40 km – From here you can TURN RIGHT and descend to Villa Dievole, ascend again to this point and continue along the wide track.

9.60 km – TURN LEFT and follow the signpost for Carpineto (0.5 km).  There is a signpost to the right for Dievole and an excellent view over the vineyards of the area from this junction.    

9.70 km – BEAR LEFT at the at the small stone building with the painted signpost for Borgo Carpineto B&B (there is a small car park on the left-hand side, then BEAR RIGHT immediately to pass between the buildings.  (From the car park don’t continue straight on down the grassy track.)

9.80 km – BEAR RIGHT next to the stone wall on your right-hand side (ignoring the track on the left) and continue descending.

9.90 km – Continue STRAIGHT ON and ignore the track off to the right.

10.00 km – Continue on the track to BEAR LEFT of Bottacio Villa.  After passing the building BEAR LEFT onto the second, slightly higher track on the left. 

10.20 km – Pass the building on your right-hand side and BEAR LEFT to stay on the track descending into the valley.  Continue on this track for ~800 m. 

11.00 km – Continue STRAIGHT ON passing the Molino del Lupo Villa buildings on your left-hand side and walk to the end of the track.  Here TURN RIGHT into the grassy clearing and walk to the far-right edge of the clearing towards the stream in the trees. 

11.20 km – On reaching the stream edge cross the stream using the stepping stones to the dirt path on the opposite bank.  Go through the woodland into the open clearing of grass and continue STRAIGHT ON to follow the dirt path ahead. 

11.40 km – Cross the stream channel over the path and continue ascending.  As the path splits in ~50 m BEAR LEFT uphill on the rough path.  Follow the path for ~500 m.

11.90 km – Continue STRAIGHT ON with the clearing on the right-hand side to follow the main track. 

12.00 km – BEAR LEFT to continue on the main track. 

12.30 km – As a track joins from the right, TURN LEFT and continue STRAIGHT ON the track to pass buildings on the right-hand side. 

12.40 km – At Tosa Villa on the left-hand side of the track with painted red and white markers on the wall continue STRAIGHT ON keeping the wall on your left-hand side.

12.60 km – With the villa gates behind you on the right join the road and BEAR RIGHT to continue STRAIGHT ON along the road to San Sano following the red and white painted markers for ~600 m. 

13.20 km – The road splits at the edge of San Sano village (with a red and white marker on the dead-end signpost on your left-hand side) BEAR RIGHT and continue uphill passing the trattoria on your right-hand side.

13.30 km – Finish in the centre of the tiny village of San Sano at the road junction with the frog fountain on your right-hand side. 


all notes on protected areas


43.422125, 11.389219
43°25'19.7"N 11°23'21.2"E
32T 693406 4810465
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. 

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Dave Pietruszynski
July 25, 2018 · Community
Nice woodland trail in Dievole Natural Park. The stream after Molina del Lupo was low enough to make an easy crossing. Some great views of Dievole Villa. The Trattoria in San Sano is closed on Wednesday, and the only other sit-down option was to organize a dinner with the proprietor of Hotel San Sano. He didn’t want to seat us until 8pm because of the heat so we opted for a panini from the little deli/wine store next to the Trattoria which was open. The Trattoria and hotel seem to work to ensure visitors have options, so just speak up.
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Photos from others

13.3 km
4:45 h
364 m
368 m
Highest point
446 m
Lowest point
264 m
Circular route Refreshment stops available Geological highlights


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