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Radda in Chianti Loop Walk via Castelvecchi & Volpaia

· 4 reviews · Hiking route · Italy
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  • Soldani Agriturismo
    Soldani Agriturismo
    Photo: Catherine Allan, Macs Adventure
m 600 500 400 300 12 10 8 6 4 2 km
Explore the iconic wine region of Chianti and visit the world-renowned Castelvecchi, and it’s neighbouring hilltop village, Volpaia.
Distance 13.5 km
5:00 h
501 m
502 m
628 m
343 m

Leave Radda in Chianti and descend on grassy tracks through the olive groves and vineyards below, then follow quiet roads and tracks ascending out of the valley passing Pieve di Santa Maria Novella to Castelvecchi – perhaps the most famous winery in Chianti.  From here follow tracks and narrow paths through wild woodland before reaching the quaint hilltop village of Volpaia.  Explore the narrow streets and indulge in a long Italian lunch before following tracks and roads back to Radda in Chianti. 

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

Author’s recommendation

For wine connoisseurs we recommend pre-booking a wine tasting, and tour at Castelvecchi.  The winery also has other options that might interest you, such as a pre-booked picnic in the vineyards with one of their bottles of Chianti wine.  See tips, hints and links below for how to book. 
Profile picture of Catherine Allan
Catherine Allan
Update: October 23, 2020
Highest point
628 m
Lowest point
343 m
Best time of year

Track types

Dirt road 1.31%Nature trail 5.57%Path 2.77%Road 7.56%Unknown 82.76%
Dirt road
0.2 km
Nature trail
0.8 km
0.4 km
1 km
11.2 km
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Safety information

The terrain varies from tarmac roads, faint grassy paths, narrow rough paths, and 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:

Make sure to bring plenty of water with you for the day's walk.  You can eat lunch in the restaurant in the village of Volpaia at approximately 8 km into the walk, but you may wish to bring snacks or a picnic lunch with you.  You may wish to check its opening times on


Points of Interest:

Castelvecchi Chianti Winery

A beautiful winery with a restaurant and ancient cellars.  Castelvecchi’s position commands excellent views over the surrounding vineyards in the valleys below.  You can arrange a wine tasting by calling the winery on 0039 0577 735612 or on their website:


The village of Volpaia is another hilltop village with fantastic views over the vineyards and olive groves surrounding it.  There are a couple of authentic Tuscan restaurants in the small village where you can have lunch.  Volpaia has it’s own website ( where you can buy local olive oils, wines, and liqueurs.


Via Roma, Radda in Chianti (529 m)
43.486549, 11.373263
43°29'11.6"N 11°22'23.7"E
32T 691910 4817583
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Via Roma, Radda in Chianti

Turn-by-turn directions

0.00 km – Today’s walk begins where the paved and pedestrianised Via Roma, joins the road Via Pianigiani.  At the road junction TURN RIGHT onto the road and leave the western end of the village.  There is no pavement for 100 m – please beware of vehicles.  

0.10 km – Continue STRAIGHT ON to follow the road Via Pianigiani and move right onto the red tiled pavement with the road on your left and metal railings and lamp posts on your right.  There are wonderful views over the surrounding country to be had from this walkway. 

0.30 km – Pass a building on your right and before the road curves away to the left TURN RIGHT off the pavement onto the track between the building you just passed and the last building on the right hand side.  Follow the track as it descends between the buildings and becomes more faint and grassy; keep the hedgerow on your right and follow the faint track down the field (olive trees on left).

0.45 km – On reaching a high fence keep it on your right until you reach the high gate.  Lift the latch at the top and pass through the gate. Then immediately TURN RIGHT to ascend for 50 m.  Keep the fence on your right and the vines on your left. 

0.50 km – TURN LEFT and keep to the edge of the vineyard with the fence on your right.  Continue STRAIGHT ON following the fence.  You will soon have an olive grove on your left. 

0.70 km – On reaching the fence that descends the hill to the track visible below TURN LEFT and descend the hill keeping the fence on your right. 

0.80 km – At the end of the grassy track (olive trees on left, and high fence on right) BEAR LEFT onto a dirt track which leads to a wider gravelly track lined with trees.  On reaching the gravelly track TURN RIGHT onto it and follow it past the agriturismo building on your right in 100 m. 

0.90 km – Continue STRAIGHT ON the road passed the agriturismo and follow the road as it descends and bears sharply to the right. 

1.00 km – At the end of the tree-lined drive go through the stone pillars and pass the Soldani winery on your right before descending to the road ahead.  On reaching the road TURN LEFT onto it and follow the road for 400 m until it splits just after a bridge.  There is no pavement so please beware of the vehicles. 

1.70 km – When the road splits after crossing the stone road bridge BEAR RIGHT onto the road signposted for Castelvecchi & Volpaia and descend slightly. 

2.40 km – As the road splits after passing a winery on the left-hand side BEAR LEFT onto the road signposted to Castelvecchi (2.5 km).  Follow this road all the way to Castelvecchi as it winds it’s way uphill. 

2.60 km – Continue STRAIGHT ON the road and pass the large salmon pond on your right. 

3.80 km – Continue STRAIGHT ON and pass the Pieve di Santa Maria Novella church on your left. 

4.80 km – You have now reached the world-famous Castelvecchi winery on your right, where you can attend pre-booked wine tastings.  Even if you haven’t booked a wine tasting you can wander through the reception area into the main courtyard and gaze out over the vineyards in the valleys below.  After some time at Castelvecchi rejoin the road and continue STRAIGHT ON for approximately 100 m. 

4.90 km – TURN RIGHT off the road onto a descending track signposted Vignamaggio (with a stone shrine to Santa Maria on your left). 

5.30 km – TURN LEFT before the high metal gate ahead onto a faint dirt path (approx. 1 m wide then narrowing with stones underfoot) in the undergrowth and trees.  In 100 m in a small clearing BEAR LEFT and continue to follow the faint path as it ascends.  Shortly the path becomes more defined and the shrubby undergrowth and bushes becomes mature forest. 

6.20 km – BEAR RIGHT on the path to cross the stream channel and immediately TURN RIGHT to continue following the path as it curves around the hillside. 

6.30 km – On reaching a gravelly clearing in the trees follow the path and continue STRAIGHT ON

6.40 km – At a track junction with a signpost for Castelvecchi on your left, TURN RIGHT onto the track and descend slightly.  In 100 m pass buildings and a hotel on your left-hand side

6.60 km – TURN LEFT in front of the fenced vineyards and follow the uneven track to descend with the high fence on your right-hand side. 

7.30 km – TURN RIGHT and continue to follow the track, ignoring the smaller track straight ahead, at the junction with the large boulder with writing on it.  The track will soon begin to ascend.

7.40 km – Continue STRAIGHT ON ignoring the track on your left.  Shortly you will come to a wooden cross and an olive grove on your right-hand side, continue STRAIGHT ON the main track.

7.70 km – BEAR RIGHT on the track, ignoring the track on the left, and continue to follow the track as it ascends to Volpaia with the stone wall on your left. 

7.80 km – The track becomes a road just after between buildings on the edge of Volpaia village.  Enter the village on the road with the church on your right-hand side and pass through the small square with the well in the centre.  Walk past the well and BEAR RIGHT where the road splits.  In 50 m before a junction with two roads, and before reaching Bar Ucci ahead on the left, BEAR RIGHT down a set of stone steps between the buildings.

7.90 km – At the base of the stone steps in a small car park continue STRAIGHT ON and walk along the dirt track ahead on the right-hand side of the arched gateway.  There is a sign for the cemetery and high stone walls on either side of the track as it descends. In 300 m pass a shrine to Santa Maria and continue STRAIGHT ON.

8.30 km – Continue STRAIGHT ON following the signs on the boulder to Casetto. 

8.40 km – TURN RIGHT at the T-junction and follow the yellow signpost for Casetto.  In 200 m ignore the track on your right and continue STRAIGHT ON to pass a building on your left. 

8.80 km – Continue STRAIGHT ON the track to pass the house on your left. 

9.20 km – Follow the tarred road as it descends and curves to the left.  Soon after BEAR RIGHT to continue on the track, ignoring another track on the left. 

9.30 km – At the junction TURN LEFT and follow the sign on the boulder for Radda in Chianti. 

9.60 km – TURN RIGHT onto the wide track and descend as it bears left.  Shortly after TURN RIGHT onto the road (opposite the Podere Terreno winery sign).  There is no pavement on the road so please beware of vehicles. Continue on the minor road until the point where you turned off for Castelvecchi. 

10.50 km – Continue STRAIGHT ON on the tarred road as it curves sharply right passing the entrance to a house on the right.

11.10 km – Cross the small stone bridge to arrive where the road splits for Castelvecchi on the right.  BEAR LEFT following the signpost for Radda in Chianti (3 km) and retrace your steps back to Radda.

11.80 km – TURN LEFT onto the larger road and cross the road bridge following the signpost for Radda in Chianti (2.5 km). 

12.30 km – TURN RIGHT the road and ascend on the track to the agriturismo and the Soldani winery on the left-hand side of the tree-lined track. 

12.70 km – Before track curves right TURN LEFT off it onto a smaller track with the vines on your left and BEAR RIGHT in 20 m to walk towards the olive grove on your right-hand side. In a further 20 m continue STRAIGHT ON the faint grassy track keeping the fence of the olive grove on your right-hand side. 

12.80 km – TURN RIGHT to follow the fence around behind the olive grove, soon after TURN LEFT and ascend for 50 m continuing to follow the fence then TURN RIGHT and follow the fence around the back of the field. 

13.00 km – TURN RIGHT and descend for 50 m to reach the gate on the left-hand side of the vineyard.  Go through the high gate and then TURN LEFT to retrace your steps and ascend the hill on the faint grassy track back to the roadside between the two buildings. 

13.20 km – Emerge from between the buildings onto the pavement.  TURN LEFT onto the road and gain the red-tiled pavement with metal railings and lampposts on the left-hand side in 50 m.  After this pavement ends walk into Radda in Chianti taking care of vehicles.

13.50 km – Finish where you began at the end of Via Roma outside the restaurant with outdoor seating.  Make sure to take time to explore the narrow streets of Radda in Chianti, with plenty of gift shops, cafes and restaurants, before your evening meal. 


all notes on protected areas


43.486549, 11.373263
43°29'11.6"N 11°22'23.7"E
32T 691910 4817583
Show on Map
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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Elizabeth Asseily
August 26, 2020 · Community
Beautiful hike with mixed terrain and incredible views. Lunch in volpaia was a great idea! My only negative is that the stretch the road was a bit long.
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When did you do this route? August 23, 2020
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Photo: Elizabeth Asseily, Community
Ellen Kelly
April 18, 2019 · Community
Great hike. Mixed terrain. Roads, towns, olive groves and trekking through the woods. So nice to have a beautiful lunch in Volpaia. The last leg back to Radda is a challenge. Totally recommend it. THANKS!
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When did you do this route? April 15, 2019
Entering Volpaia
Photo: Ellen Kelly, Community
Dave Pietruszynski
July 21, 2018 · Community
Spectacular views with solitude. Vineyards and olive groves. Remember the steep drop from the walled village at the beginning of the trek! Save some energy at the end to climb back up. Some care needed when hiking on roads- blind turns and two narrow one lane bridges.
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13.5 km
5:00 h
501 m
502 m
Highest point
628 m
Lowest point
343 m
Circular route Scenic Refreshment stops available Cultural/historical interest


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