Historic Centre of Pienza – Pienza loop from Rapolano Terme

Historic Centre of Pienza – Pienza loop from Rapolano Terme

Hard

5.0

(1)

riders

Historic Centre of Pienza – Pienza loop from Rapolano Terme

05:54

86.9km

1,400m

Gravel riding

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: September 3, 2026

Tips

Includes a segment in which cycling is not permitted

After 64.8 km for 225 m

Waypoints

Start point

Train Station

Get Directions

9.28 km

Necropoli Etrusca di Poggio Pinci

Archaeological Site

39.6 km

Viewpoint

40.7 km

Panoramic view

Highlight • Viewpoint

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

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42.9 km

View of Pienza

Highlight • Viewpoint

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

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45.3 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 …

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45.4 km

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.

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64.2 km

San Giovanni d'Asso Historic Village

Highlight • Settlement

San Giovanni is a characteristic village which is located in an elevated position and allows you to fully enjoy the view of the Crete Senesi.

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64.8 km

Bosco della Ragnaia

Forest

71.0 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

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71.0 km

View of Baccoleno

Highlight • Viewpoint

Unfortunately the entrance to get to the famous writing "Baccoleno" has been closed. Too bad, because from there the view is spectacular

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71.3 km

Beautiful scenic viewpoint

Highlight • Viewpoint

This 5 star viewpoint is just off the main road. A winding avenue of cypress trees leads to a residence in an enviable location. Truly Tuscan landscape.

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86.9 km

End point

Train Station

Way Types & Surfaces

Way Types

45.4 km

31.7 km

9.44 km

296 m

167 m

Surfaces

39.5 km

26.7 km

19.9 km

434 m

271 m

225 m

Elevation

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

Highest point (490 m)

Lowest point (180 m)

Weather

Tuesday 20 October

19°C

13°C

-- %

Additional weather tips

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Comments

December 30, 2024,💥 Ultimo Giro del 2024 VAL d’Orcia 💥

💥And with this great tour we say goodbye to 2024 🥂with another fantastic 📈 route.
Today, braving the polar ❄️cold of the morning, we started from 📍Rapolano Terme from the Parco dell’acqua (home of the 4th edition of ⭐️ 80 Voglia di Gravel ⭐️ ) and tried some parts of the 🟤 Trail 🟤 .
Super day and incredible 🏙️ …

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