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Montepulciano to Pienza

· 1 review · Hiking trail · Siena
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Macs Adventure Verified partner  Explorers Choice 
  • View from lunch spot
    / View from lunch spot
    Photo: Sally Thompson, Macs Adventure
  • / View from Montichiello
    Photo: Sally Thompson, Macs Adventure
  • / Montichiello
    Photo: Sally Thompson, Macs Adventure
  • / Pienza getting closer
    Photo: Sally Thompson, Macs Adventure
  • / Butterfly
    Photo: Sally Thompson, Macs Adventure
  • / Leaving through the old gate in Montepulciano
    Photo: Sally Thompson, Macs Adventure
  • / Vineyards en route
    Photo: Sally Thompson, Macs Adventure
m 700 600 500 400 300 14 12 10 8 6 4 2 km

A lovely walk through undulating and iconic landscapes, passing wineries, vineyards and olive groves galore and finishing in the splendid hill top town of Pienza.

15.5 km
4:45 h
490 m
543 m

Make your way out of Montepulciano and through one of the town's old gates before heading out into the surrounding countryside. Upon reaching San Bagio Church you will then be walking along gravel roads and past vineyards and olive groves, with Montepulciano getting smaller and smaller as you get further away from it. From the trail as you walk onto a plateau there are really great views. At times you can see Monticchiello and even Pienza in the distance. Descend for a time from the plateau and then ascend to the lovely little village of Monticchielo where you may have lunch or a refreshment. Then retrace your steps for a while descending into the wide valley before ascending again, There will be one more brief descent before making your way uphill to the very pretty hill top town of Pienza.

Author’s recommendation

Definitely do not miss out on a visit to to the little village of Monticchiello from where there are amazing views across the stunning countryside all the way to Pienza. Why not sit on the terrace of a little cafe or eat your picnic lunch from the view point just before you walk through the village gate. User
Sally Thompson
Updated: December 07, 2017

Highest point
600 m
Lowest point
333 m
Best time of year

Safety information

At times you have to walk along roads with traffic. Even though they are not very busy it is always a good idea to be vigilant.

If you are walking during the hot months we recommend starting the walk very early in the morning, then spending a couple of hours in Monticchiello, continuing to walk when the heat of the day has passed. You could have an extended lunch for just rest under the shade of an olive tree (which is what the author did). Please be aware however that the restaurants do not generally start serving lunch until 12.30pm.


Make sure you use sunscreen and a hat when it is hot and take plenty of water. Sturdy walking boots and shoes are required. Most of today's walking is along gravel roads, which can be tough on the feet.

Tips, hints and links


Food & Drink ...

You can find a few cafes in Monticchiello village which is situated along your walk today. However most do not start serving lunch until 12:30pm. Or you can take a packed lunch. There are plenty of places in Montepulciano in which to buy provisions for a picnic lunch.


Some useful links ...


San Bagio Church

A beautiful domed 16th century church: this church, situated just outside of Montepulciano is considered to be Antonio da Sangallo's masterpiece. It is in the shape of a Greek cross and its design is heavily influenced by Bramante's plan for St Peter's in Rome. There are 3 orders of columns on the free-standing tower, Doric, Ionic and Corinthian. Make sure you take the time to look inside the interior.,_Montepulciano



Hilltop walled village of Monticchielo: The town is said to have been founded more than 1000 years ago, although the oldest structures seen today are the walls and their associated towers, and the church, both dating back 850 years! Apart from these the pleasure of a visit comes from simply strolling through the ancient streets.



Pienza is a UNESCO World Heritage Site: The main buildings including the cathedral, town hall adn the papal residence, all of which surround the town square (where your walk finishes) were built in just 3 years! The Pope then decreed that none of these buildings should ever be changed. Pienza has a small population of 2,300. Some of the shots from the movie "The English Patient" were filmed att the nearby Sant 'Anna Monastery. Don't miss the short walk along the wall on the southern edge of town with its wonderful views.


This activity is included in the following itineraries:




On Via di Griacciano del Corso in Piazza Michelozzo (551 m)
43.095497, 11.783800
32T 726557 4775181


Piazza Pio II in Pienza

Turn-by-turn directions

0.0km – In Piazza Michelozzo and with your back to the church TURN RIGHT and walk up Via di Gracciano.

0.1 km- After 100m come to a T-Junction (Piazza del Erbe and with stone archways in front of you) and TURN LEFT walking up Via L’Erbe. After 20m you will see some stone steps on your right. TURN RIGHT and walk to the top of the steps. Then TURN LEFT and walk up Via del Poggiolo.

0.3km – Come to a junction of streets and continue STRAIGHT ON down Via del Paolino and under the archway. After about 40m TURN SHARP RIGHT (where there is a no through road sign in front of you) and keep descending down the same road as it then bends left. You are now on Via dei Grassi. After another 300m or so pass through another archway and go STRAIGHT ON descending down the same road until you reach the San Bagio Church.

1.0km – In front of the church TURN LEFT down this road so that the church is on your right and then bear right behind the back of the church. (As you bear right you will see a red and white trail sign on your right saying San Bagio 495m, etc and on your left there is an olive tree grove).

1.2km – After circling the church and ignoring the first dirt road off to your left, TURN LEFT down the gravel road (Via di Pescata). You can also spot a red and white wooden sign for Sentiero della via Barlettaia, you will see quite a number of these signs all the way to Pienza and from now on. Continue walking down the same road for 500m, ignoring any turns off to the left and right.

1.7km – At this point continue STRAIGHT ON down a narrower stone/dirt trail and ignoring the turn on the right to the Agrituristica Pescaia. After a further 200m ignore trail up to the left and carry STRAIGHT ON along the same trail (with grassy middle).

2.2km – At the end of this trail TURN LEFT ascending up the gravel road and following the wooden arrow with a red tip pointing left.

2.6km – At the T-Junction (and at the end of the gravel road) TURN RIGHT and walk along the main road for 400m using the grass verge to walk on where possible and being careful of traffic.

3.0km – TURN LEFT up smaller tarmac road (Via di Poggiano) and with red and white signs. Walk up this road ascending for 500m.

3.5km – TURN LEFT onto a smaller gravel road (Via del Termine) and with red and white signs. Continue along this road, ignoring any trails, roads, driveways off to the left and right for a further 1.7km.

5.2km – At fork in the road BEAR RIGHT (following red and white wooden signs on your right and signposted to Spedaletto) and continue to follow the same road ignoring any side trails and occasionally seeing red and white signs and at one time an arrow.

7.5km – At the red and white signs on the right of you (both signposted towards Monticchiello, go STRAIGHT ON, ignoring the track ascending to the left.

7.9km - At the junction of pathways go STRAIGHT ON ignoring all other turns off to the left and right. The gravel trail then ascends.

8.2km – At the T-Junction TURN LEFT (with the red and white signposts in front of you signposted to Monticchiello) and keep ascending on the same road for 600m.

8.8km – At the stop sign TURN LEFT and walk down Viale Marino Capelli.

9.1km – At the T-Junction TURN LEFT (with the stone wall and wooden fence in front of you) and walk up into the village.

9.3km – At the archway to the village you can take time to now to explore Monticchiello.

Once you have taken time here you can simply return to the arch and then retrace your steps (by turning next right, then next right again until you come to the same place that you were at 8.2km).

10.4km- Once back at this point (keep STRAIGHT ON descending down the same gravel road as it bends left. You can now see Pienza on the hill top in the distance in front of you.

11.2km - At the junction TURN RIGHT, crossing the bridge and following the red and white signs to Spedaletto and the big blue sign for Pienza (please watch out for traffic on this narrow bridge). The road then veers left, simply follow it until you reach the next junction in 200m.

11.5km - TURN LEFT following the red and white signs to Spedaletto and walk along a narrower road which changes from tarmac to gravel. Keep walking along this road for a further 600m.

12.1km – At the junction TURN RIGHT up the gravel road ascending and ignoring the gravel road that goes straight on. Again you will be following red and white signs towards Pienza and also a faint brown sign that also directs you right.  Stay in the same road as it ascends and winds and even when it begins to descend for a further 2.3km.

14.4km – At the junction with red and white wooden signs TURN LEFT towards Cacciaconti/Albergo/Miniera and keep ascending to the village for almost another km.

15.3km – At the top of this road with red and white signs on your left and an archway in front of you go STRAIGHT ON, crossing the road and walking under the arch (Porta Al Ciglio). You are now on the Corso di Rossellino. Walk up this street until you reach Pienza’s main square.

15.6km – The walk finishes in the main square of Piazza PIo II.


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Roslyn Owen
October 10, 2019 · Community
Wonderful hike, glad we went in cooler weather.
show more
Thursday, October 10, 2019 9:14:34 PM
Photo: Roslyn Owen, Community

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15.5 km
4:45 h
490 m
543 m
Scenic With refreshment stops


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