RoutesPlannerFeaturesUpdates
App
Login or Signup
Get the App
Login or Signup
Login or Signup
Routes
Italy
Tuscany
Tuscany
Siena
Chianciano Terme

Historic Centre of Pienza – Pienza loop from Chianciano Terme

Routes
Italy
Tuscany
Tuscany
Siena
Chianciano Terme

Historic Centre of Pienza – Pienza loop from Chianciano Terme

Hard

4.8

(12)

66

riders

Historic Centre of Pienza – Pienza loop from Chianciano Terme

04:04

52.7km

1,290m

Gravel riding

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: September 10, 2026

Waypoints

A

Start point

Parking

Get Directions

11.7 km

cipressi di Monticchielo

Viewpoint

2

13.3 km

View of the countryside between Pienza and Monticchiello

Highlight • Viewpoint

It's always worth it, but spring is the most beautiful time

Translated by Google •

Tip by

3

14.8 km

Panoramic view

Highlight • Viewpoint

This view motivates you to continue driving to the next ice cream parlor!

Translated by Google •

Tip by

4

16.9 km

View of Pienza

Highlight • Viewpoint

Beautiful view of Pienza, a typical Tuscan town worth seeing.

Translated by Google •

Tip by

5

19.3 km

Historic Centre of Pienza

Highlight • Historical Site

Pienza is a small jewel of the Val d'Orcia, known as the city of Pope Pius II, aka Enea Silvio Piccolomini, who was born here in 1405. Pius II, once …

Translated by Google •

Tip by

6

19.6 km

Pienza Historic Center and View of Val d'Orcia

Highlight • Historical Site

Immersed in the green heart of the Val d'Orcia, Pienza stands before your eyes like a Renaissance monument solidified over time. Pope Pius II wanted it and built it as …

Translated by Google •

Tip by

7

20.1 km

Pienza

Highlight • Settlement

A medieval city, awarded by UNESCO as a World Heritage Site. You can enjoy some old churches and palaces here or simply stroll through the atmospheric streets. Also the view from the city wall is great.

Translated by Google •

Tip by

8

21.4 km

Cypress-Lined Farmhouse in Tuscany

Highlight • Viewpoint

Typical country house on a hilltop. Simply a beautiful motif.

Translated by Google •

Tip by

9

30.2 km

View of the Tuscan Countryside

Highlight • Viewpoint

Along the road that goes from Montefollonico to Palazzo Massaini there is a trail that winds through the heart of the Tuscan countryside, among rolling hills, cultivated fields and ancient residences.

Translated by Google •

Tip by

42.1 km

Contucci Palace

Castle

49.2 km

Troscia maledetta

Lake

B

52.7 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

19.4 km

17.5 km

13.0 km

2.22 km

578 m

Surfaces

23.8 km

13.2 km

11.5 km

1.93 km

1.67 km

558 m

Sign up to see more specific route details

Sign up for free

Elevation

Elevation
Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (680 m)

Lowest point (330 m)

Sign up to see more specific route details

Sign up for free

Weather

Powered by Foreca

Friday 23 October

16°C

7°C

39 %

Additional weather tips

There’s a fairly high chance of rain. Consider packing a waterproof jacket.

to get more detailed weather forecasts along your route

Comments

guide_signup

Want to know more?

Sign up for a free komoot account to join the conversation.

Sign up for free

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

NavigateSend to Phone
Save
Edit route
Download GPX
Move start point
Print
Share
Embed on a website
Report an Issue
Report restricted access

Nearby routes

Hard

5.0

684

Monte Sante Marie – Monte Sante Marie Gravel Road loop from Buonconvento

06:44h

105km

1,510m

Hard

4.6

233

Buonconvento – Cypress Road to Buonconvento loop from San Quirico d'Orcia

03:37h

51.7km

980m

Hard

5.0

735

Buonconvento – Colle Pinzuto loop from Buonconvento

06:58h

110km

1,650m

Hard

4.9

217

San Quirico d'Orcia – Val d'Orcia Panorama loop from Castelmuzio

03:30h

48.0km

1,010m

Hard

4.9

284

San Quirico d'Orcia – Val d'Orcia Panorama loop from Torrenieri-Montalcino

03:09h

45.2km

880m

Hard

4.7

234

Val d'Orcia Panorama – View of Pienza loop from San Quirico d'Orcia

01:53h

28.3km

550m

Hard

4.9

245

Buonconvento – Monte Sante Marie Gravel Road loop from Buonconvento

06:17h

98.8km

1,590m

Hard

5.0

180

Monte Sante Marie Gravel Road – Piazza del Campo loop from Asciano M. Oliveto M.

06:16h

90.1km

1,660m

Hard

4.9

146

Via Francigena Gravel Route – Strade Bianche Radi loop from Podere Il Moro

03:21h

54.6km

560m

Hard

4.7

144

Val d'Orcia Panorama – View of Val d'Orcia loop from Bagno Vignoni

04:23h

60.7km

1,490m

Hard

5.0

106

Porta Romana (Siena) – Pienza loop from Buonconvento

09:46h

136km

2,180m

Hard

4.7

195

Val d'Orcia Panorama – View of Pienza loop from Pienza

02:00h

29.1km

560m

Explore
RoutesRoute plannerFeaturesRedeem a voucherHikesMTB TrailsRoad cycling routesBikepackingSitemap
B2B
PartnersConnectEmbed routes
Company
PressWhat's NewPioneersProduct UpdatesAmbassadorsAdventure HubCareers
Community
Help GuidesSupportGPX Merge ToolGPX Route VideoHazard AssessmentLive TrackingExperiencesGroups
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy
Terms of Service
Community guidelines
Vulnerability disclosure program
Imprint
Information for law enforcement