Massaini Castle – View of Val d'Orcia loop from San Quirico d'Orcia

Massaini Castle – View of Val d'Orcia loop from San Quirico d'Orcia

Hard

4.8

(6)

217

riders

Massaini Castle – View of Val d'Orcia loop from San Quirico d'Orcia

03:05

63.2km

920m

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: September 25, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Riserva Naturale Lucciola Bella

Waypoints

Start point

Bus stop

Get Directions

21.7 km

View of the Cypress Road at La Foce

Highlight • Viewpoint

Stunning view!

Tip by

22.1 km

Passo La Foce

Mountain Pass

38.7 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.

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Tip by

40.7 km

San Biagio Church (Montepulciano)

Highlight • Religious Site

At the foot of Montepulciano, the Temple of San Biagio represents a masterpiece of the Tuscan Renaissance. A work by Antonio da Sangallo the Elder, it is distinguished by the …

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40.9 km

Avenue of Remembrance

Highlight • Monument

Conceived as a monumental link between the Temple of S. Biagio and the Old Cemetery, it consists of two rows of cypresses arranged on the sides of the road. At …

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49.7 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

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60.8 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 …

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Tip by

63.2 km

End point

Bus stop

Way Types & Surfaces

Way Types

30.8 km

30.7 km

1.70 km

< 100 m

Surfaces

62.6 km

592 m

< 100 m

Elevation

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

Highest point (570 m)

Lowest point (250 m)

Weather

Saturday 24 October

16°C

4°C

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Comments

July 19, 2025,Giro in bici da corsa ad anello da San Quirico a Chianciano

A stunning loop of approximately 60 km through the Tuscan hills, starting in San Quirico d'Orcia. It passes through Pienza, Monticchiello, and Montepulciano, gently climbing to Chianciano Terme, before returning via the southern Lucciola Bella Nature Reserve and Bagno Vignoni. The route is almost entirely paved, with gentle climbs, scenic descents, and breathtaking views of the Val d'Orcia and Val …

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