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December 13, 2022
Road cycling

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Nearby routes
Best routes near Massaini Castle

4.7
(11)
232
riders
45.0km
02:22
840m
840m
Embark on a moderate 28.0-mile (45.0 km) racebike journey through Tuscany's Val d'Orcia, a UNESCO World Heritage Site. This round trip features 2749 feet (838 metres) of elevation gain and takes about 2 hours and 22 minutes to complete. You will navigate undulating Tuscan hills, cycling on a mix of paved roads and the famous unpaved gravel "strade bianche," passing through areas like the lunar-like Crete Senesi and cypress-lined avenues. Expect panoramic views and the chance to see picturesque medieval villages like Monticchiello and the Renaissance architecture of Pienza.
Be prepared for the unique terrain; the gravel roads, made of limestone, can be smooth in some parts but also rough with stones, especially after rain. While there are no single major ascents, the route includes numerous climbs, with gradients often reaching 8% and sometimes peaking at 15%. This trail requires good fitness, as the challenging gravel sectors involve constant ups and downs, and you might even need to push your bike in parts.
This route is more than just a ride; it is a deep cycling experience that combines physical demands with cultural immersion. The "strade bianche" are the namesake and inspiration for the professional Strade Bianche cycling race and the L'Eroica vintage bike race, making this region a pilgrimage for cycling enthusiasts. You can also explore historic towns like Montepulciano, enjoy local food and wine, and visit ancient cellars along the way.

4.7
(3)
119
riders
73.9km
03:37
1,120m
1,130m
Embark on a challenging road cycling loop through the heart of Tuscany, starting from Montalcino. This difficult 45.9-mile (73.9 km) route, with its 3679 feet (1121 metres) of elevation gain, typically takes around 3 hours and 36 minutes to complete. You will ride through undulating green hills, past expansive vineyards and ancient olive groves, and along cypress-lined roads, all while enjoying panoramic views of the Val d'Orcia.
Prepare for a demanding ride that requires very good fitness, as the route features steep climbs and some challenging "strade bianche," or white roads. While mostly well-paved, certain unpaved segments may be difficult to ride, and you might need to push your bike at times. Plan your hydration and nutrition carefully for this sustained effort across the hilly landscape.
This loop offers a classic Tuscan cycling experience, connecting the historically significant towns of Montalcino and Montefollonico. The inclusion of "strade bianche" echoes the famous L'Eroica event, celebrating the region's unique gravel roads and cycling heritage. You will immerse yourself in the natural beauty and cultural richness of the Val d'Orcia, a UNESCO World Heritage Site.

43
riders
80.0km
04:07
1,420m
1,420m
This difficult 49.7-mile road cycling loop from San Quirico d'Orcia to Montepulciano offers challenging climbs and iconic Val d'Orcia views.
Details
Informations
Elevation 470 m
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Wednesday 13 May
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