Highlight (Segment) • Viewpoint
Legendary Road of Monticchiello
Road cycling
4.8
(24)
Gravel riding
5.0
(1)
Mountain biking
5.0
(1)
Tips
December 13, 2022
Road cycling
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Nearby routes
Best routes near Legendary Road of Monticchiello
4.6
(21)
329
riders
79.4km
03:59
1,300m
1,300m
This difficult racebike loop through Tuscany's Val d'Orcia covers 49.3 miles (79.4 km) with a significant 4250 feet (1295 metres) of elevation gain, taking about 3 hours and 59 minutes to complete. You will cycle through iconic rolling Sienese hills, past picturesque vineyards, and along cypress-lined avenues that define this UNESCO World Heritage site. The route connects historic towns like Montalcino and Montepulciano, offering spectacular views, especially from Montalcino's fortress. Prepare for a challenging yet rewarding ride through some of Italy's most celebrated landscapes.
This route is designed for experienced racebike riders with very good fitness levels, given the substantial elevation changes and gradients that can reach 12%. While most of the path is paved, be ready for short sections of unpaved roads, cobblestones, or compacted gravel. When you reach towns like Montepulciano, you will find steep streets; it is best to explore Pienza's historic center on foot, as cycling there is not recommended. Consider starting early to make the most of the daylight and avoid the midday heat, especially during warmer months.
The Val d'Orcia is renowned for its classic Tuscan scenery, a landscape so distinctive it has been recognized as a UNESCO World Heritage site. This area is famous for its wine production, particularly around Montalcino and Montepulciano, making it a cultural and gastronomic highlight. You will experience the region's unique blend of natural beauty and historical charm, with opportunities to see the 'Legendary Road of Monticchiello' for truly memorable vistas. This loop offers a deep dive into the heart of Tuscany.
4.8
(12)
237
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.
44
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
Distance 1.11 km
Uphill 100 m
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Thursday 11 June
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