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Cypress Road to Buonconvento – Historic town of Montalcino loop from San Quirico d'Orcia

Cypress Road to Buonconvento – Historic town of Montalcino loop from San Quirico d'Orcia

Hard

riders

Cypress Road to Buonconvento – Historic town of Montalcino loop from San Quirico d'Orcia

04:31

59.4km

1,210m

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: May 19, 2026

Tips

Includes a very steep uphill segment

You may need to push your bike.

After 28.7 km for 72 m

Waypoints

Start point

Bus stop

Get Directions

11.0 km

Nice up and down gravel section

Highlight (Segment) • Trail

Explore this beautiful stretch of up and down dirt road, located right on the outskirts of the historic city of Siena. Its beauty lies in the breathtaking views that open up along the way, offering a unique and immersive cycling experience.

Translated by Google •

Tip by

14.8 km

Beautiful View

Highlight • Viewpoint

Really spectacular view spot looking over a road that’s framed by Cypress Pines

Tip by

15.8 km

Cypress Road to Buonconvento

Highlight • Trail

A must to do both on foot and by bike. There are many places to take beautiful souvenir photos.

Translated by Google •

Tip by

16.1 km

Cypress-lined avenue to Azienda Agricola Caparzo

Highlight • Trail

iconic structure that deserves a souvenir photo, from here onwards a wonderful view over the valley

Translated by Google •

Tip by

16.5 km

Via Francigena Gravel Route

Highlight • Trail

La Vera Toscana gravel

Translated by Google •

Tip by

39.9 km

Montalcino Fortress

Highlight • Castle

The historic center of Montalcino is dominated by the mighty Rocca, a fortress built in 1361 to mark the passage of the city under the dominion of Siena. The panorama that can be enjoyed from the ramparts of the fortress is truly spectacular; it goes from Monte Amiata, through the Crete up to Siena, and crosses the whole Val d'Orcia up to the Maremma hills.
Source, discovertuscany.com

Translated by Google •

Tip by

40.1 km

Historic town of Montalcino

Highlight • Settlement

Montalcino, a medieval village in the province of Siena, is a place that invites you to immerse yourself in a slow tourism experience. Its trails, such as the Brunello Crossing and the Granfondo del Brunello, offer the opportunity to explore the region both on foot and on two wheels. The well-preserved historic center of Montalcino can be explored on foot without difficulty. As you approach Montalcino, don't miss its fortress, one of the main attractions of the Val d'Orcia.

Translated by Google •

Tip by

44.6 km

Gravel Road Through the Vineyards of Montalcino

Highlight (Segment) • Trail

Superb views of Montalcino and the surrounding vinyards

Tip by

59.4 km

End point

Bus stop

Way Types & Surfaces

Way Types

31.2 km

18.0 km

9.11 km

998 m

130 m

Surfaces

31.8 km

14.2 km

11.3 km

1.12 km

916 m

Elevation

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

Highest point (610 m)

Lowest point (140 m)

Weather

Monday 13 July

36°C

21°C

-- %

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Comments

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Cypress Road to Buonconvento – Historic town of Montalcino loop from San Quirico d'Orcia

Nice up and down gravel section

Beautiful View

Cypress Road to Buonconvento

Cypress-lined avenue to Azienda Agricola Caparzo

Via Francigena Gravel Route

Montalcino Fortress

Historic town of Montalcino

Gravel Road Through the Vineyards of Montalcino

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