Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Road cycling routes
Italy
Tuscany
Siena
Montepulciano

Beautiful view over the Crete Senesi region! – Tuscan Vineyard Landscape loop from Montepulciano

Routes
Road cycling routes
Italy
Tuscany
Siena
Montepulciano

Beautiful view over the Crete Senesi region! – Tuscan Vineyard Landscape loop from Montepulciano

Hard

5.0

(5)

159

riders

Beautiful view over the Crete Senesi region! – Tuscan Vineyard Landscape loop from Montepulciano

04:17

88.6km

1,280m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: August 17, 2026

Waypoints

A

Start point

Train Station

Get Directions

1

32.3 km

Beautiful view over the Crete Senesi region!

Highlight • Viewpoint

Once you pass the gate as you finish the climb, continue until you see a narrow foot path on your right side which you can cycle on. Take this and the view over the hill awaits

Tip by

34.0 km

Toscana sunset

Viewpoint

3

53.3 km

Tuscan Vineyard Landscape

Highlight • Natural

I crossed it in the middle of August, the thermometer at 44 degrees, I will remember it for a long time...

Translated by Google •

Tip by

4

54.9 km

Historic center of San Quirico d'Orcia

Highlight • Historical Site

San Quirico d'Orcia is one of the most historic and beautiful centers in the entire Val d'Orcia. Its history is thousands of years old and the center of San Quirico …

Translated by Google •

Tip by

5

57.2 km

View of Val d'Orcia

Highlight • Viewpoint

6

64.8 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

7

68.7 km

Massaini Castle

Highlight • Castle

Among vineyards, olive groves and medicinal plants, stands Palazzo Massaini, a place where nature, tradition, Tuscan food and wine merge.
Source: palazzomassaini.com

Translated by Google •

Tip by

8

77.7 km

Church of San Biagio

Highlight • Religious Site

Walking along the two parallel rows of cypresses it is possible to slowly glimpse the foreshortening of the bell tower that stands out high in the sky. And it seems …

Translated by Google •

Tip by

9

79.8 km

Church of St. Agnes

Highlight • Religious Site

Baroque and neo-Romanesque style church.
It was built in 1306 by the abbess of Poliziana Agnese. At the end of the seventeenth century it was radically renovated.

Translated by Google •

Tip by

B

88.6 km

End point

Train Station

Loading

Way Types & Surfaces

Way Types

65.4 km

21.4 km

1.48 km

326 m

< 100 m

Surfaces

87.4 km

1.05 km

240 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 (560 m)

Lowest point (240 m)

Sign up to see more specific route details

Sign up for free

Weather

Powered by Foreca

Tuesday 1 September

33°C

17°C

-- %

Additional weather tips

Max wind speed: -- km/h

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.

Navigate

Send to Phone

Save

Edit route

Download GPX

Move start point

Print

Share

Embed on a website

Report an Issue

Report restricted access

Nearby routes

Moderate

4.6

1,752

Loop tour of Lago di Trasimeno from Castiglione del Lago

02:26h

59.7km

320m

Moderate

4.8

243

Strade Bianche di Pienza e Montepulciano – round trip

02:22h

45.0km

840m

Moderate

4.7

167

The hills on Lake Trasimeno – loop from Passignano

02:05h

38.5km

760m

Hard

5.0

81

Lago Trasimeno — ring tour from Montepulciano

04:20h

96.4km

950m

Hard

53

Val d'Orcia Loop: San Quirico, Pienza & Montepulciano

04:07h

80.0km

1,420m

Moderate

4.9

413

Montepulciano – Historic Centre of Pienza loop from Montepulciano

02:43h

56.1km

770m

Moderate

4.6

330

Castiglion Fiorentino – The mouth loop from Montagnano

02:28h

55.1km

550m

Hard

4.0

268

View of Val d'Orcia – Tuscan Vineyard Landscape loop from Montefollonico

03:10h

62.4km

1,040m

Hard

4.7

244

Historic Centre of Pienza – View of Val d'Orcia loop from Montepulciano

04:31h

86.3km

1,570m

Hard

4.4

271

View of lake Trasimeno – Panorama over Lake Trasimeno loop from Passignano sul Trasimeno

03:15h

61.5km

1,050m

Hard

4.4

238

Panorama over Lake Trasimeno – View of lake Trasimeno loop from Cortona

03:14h

59.6km

1,180m

Moderate

5.0

226

Asciano Historic Center – View of Baccoleno loop from Rapolano Terme

03:03h

67.6km

750m

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