Tuscany: Hiking from Castelnuovo dell’Abate to Rocca d’Orcia

The walk described below is one of the walks included in our Self-Guided Tuscany Hiking Tour. These are the actual instructions given to our clients when they take this tour.

Our tours include hotels, a tour rep, luggage transfers while you walk, arrival/departure transfers, a cellphone for emergencies, a guide to the local sites, and other travel assistance. Please check out our main walking tours site to find out more.

Each instruction is preceded by the number of meters from the prior instruction – in other words, how many meters you will have walked in order to arrive at the current instruction.

Castelnuovo dell’Abate to Rocca d’Orcia

Distance: 13.5k
Total climb: 560m

Castelnuovo dell’Abate is a charming village perched above the Abbey of Sant’Antimo, a few kilometers south of Montalcino. Be sure to visit the abbey before starting your walk – it’s a Romanesque jewel fashioned of travertine and alabaster. The finishing point of the walk, Rocca d’Orcia, is a medieval village overlooked by an impressive fortification. Between the two lies the relatively wild valley of the Orcia River, with no villages and few habitations between (so bring along a picnic and whatever toiletries you deem necessary).

Facing the stop sign at the main intersection in front of Castelnuovo dell’Abate, turn right, direction Seggiano and follow along the main asphalt road.

550m You pass the driveway of Poggio di Sotto and continue along the asphalt.

650m Watch for where the road bends to the right in front of a vineyard. There are a couple dozen large stones laid in a row along the side of the road on your right. In front of the stones, on your left, you’ll see a dirt road. Turn onto this.

150m At the intersection next to the old stone basin bear right along the main road.

500m Bear right past the entrance to Az. Agr. Molino di Sant’Antimo. Stay on the main road, ignoring minor tracks that lead off of it, as it descends into the river valley.

900m You cross a bridge over the railroad and soon after follow along the left edge of a large flat field prepared as a vineyard.

220m When you reach the corner of the field, there is a clump of brush. Straight ahead, beyond the clump, is a small concrete bridge over a ditch. Go across this and proceed along the dirt track. You are now approximately paralleling the river on your right. You can also see the railroad bed ahead of you. Eventually you see a railroad bridge ahead of you. Continue to the bridge.

750m As you near the railroad bridge, you will need to cut across the field towards the corner of the bridge where the concrete meets the fence. You should find a pile of stones at this point which you can use to step up onto the concrete. Basically you’ll need to scramble up onto the railroad bed and cross the bridge. This track is used for a train that only passes a few times each week, so the chances of meeting it are very slim. In any case, keep to the side and you will be perfectly safe.

100m Once over the bridge, on your right, you’ll see a gate in the fence below you. There are some steps here. Go down and through the gate, making sure to close it after you. Turn left and follow along the fence.

120m At the railroad overpass, turn right onto the faint grassy track.

150m At the T-intersection with the more well-defined track, turn left and towards the group of buildings.

350m At the fence around the group of buildings, turn right and follow along the fence to the corner and then follow left around the corner.

200m Turn hard right onto the main road and continue up along this cypress-lined road.

800m Continue past the farmhouse. A german shepherd and a smaller dog are likely to come and bark at you but won’t bother you if you mind your own business. The road winds upwards, turning first to the left, then to the right, then left and past a driveway signposted P.S. Cristoforo, and finally a little zigzag bearing to the right.

600m At the top of this “zigzag”, you’ll arrive at a fork. The main road bears off to the right. There is a smaller track 90° to your left. Ignore this. Instead, go straight onto the track ahead of you that roughly parallels the main road.

800m Just before you reach the large gravel road, there is a fork. It doesn’t matter which fork you choose as both let out onto the main road, where you turn left and downhill past the pond (dry in hot weather). Look to your right above the pond and you’ll see the Castello di Ripa d’0rcia. This castle is still owned by a branch of the Piccolomini family.

150m At the T-intersection 30 meters past the green utility shed and in full view of the house, turn right. Ignore any minor tracks leading off this road.

1000m At the T-intersection in front of the ruined farmhouse, pass by the house, keeping straight and downhill. (If the way past the house is blocked for any reason, you’ll find a fork eighty meters before you arrive at the house leading to the left downhill. You can also follow this track.)

150m Stay on the main track as it turns to the right when it meets another track from the left (this other track is the one mentioned just above.)

80m Continue straight (right) at the the next fork onto the smaller track. Do NOT bear left downhill with the main track.

1400m When you arrive at a T-intersection, bear left. The right hand path just leads into a field after thirty meters. You’ll see a CAI marker on a young oak to the left of the correct path.

400m Arriving at the next T-intersection, turn right and uphill. From here you have your first view during this walk of Rocca d’Orcia, your destination for today.

200m Continue past the white house on your right and the open shed on your left.

60m At the T-intersection above the open shed turn right.

130m Continue past the yellow house. There is a dog here that will ignore you if you do likewise to him. Continue along the main road, enjoying the progressively closer views of the Rocca.

1700m At the intersection at the base of the hill on which the Rocca sits, turn left.

250m Arriving in the village, bear left through the fork. As you arrive in the village, on the right, is a house (“Katharine Domus”) where Saint Catherine of Siena, patron saint of Italy, recuperated from an illness. Continue up to the top of the town, where you’ll find the entrance to the Rocca, for a magnificent view from the ramparts of the entire sweep of the Val d’Orcia.