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Montepulciano

The best cycling routes around Montepulciano

4.4

(358)

2,161

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105

rides

Touring cycling routes around Montepulciano traverse a landscape characterized by rolling hills, expansive vineyards, and ancient olive groves. The region features iconic cypress-lined roads and "strade bianche" (white gravel roads), offering panoramic views across the Val d'Orcia and Val di Chiana. Distant views of the Monte Amiata volcano are also present on some routes, alongside unique geological formations like the Balze.

Best touring cycling routes around Montepulciano

  • The most popular touring cycling route is Montepulciano and its cypresses — Ring tour, a 13.7 miles (22.1 km) trail that takes 1 hour 50 minutes to complete. This route features significant elevation gain through the Tuscan countryside.
  • Another top favourite among local touring cyclists is Monticchiello – Pienza loop from Montepulciano, a difficult 28.0 miles (45.0 km) path. This route connects charming medieval villages and offers expansive views of the Val d'Orcia.
  • Local touring cyclists also love the View of Pienza – Pienza loop from Fattoria Buca Nuova, a 22.8 miles (36.7 km) trail leading through rolling hills and agricultural landscapes, often completed in about 2 hours 53 minutes.
  • Touring cycling around Montepulciano is defined by rolling hills, vineyards, and cypress-lined roads. The network offers options for different ability levels, from moderate to difficult.
  • The routes in Montepulciano are highly rated by the komoot community with an average score of 4.5 stars from over 250 reviews. More than 1900 touring cyclists have used komoot to explore Montepulciano's varied terrain.

Last updated: May 11, 2026

4.0

(15)

39

riders

#1.

Montepulciano and its cypresses — Ring tour

22.1km

01:50

540m

540m

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

4.3

(25)

164

riders

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

4.3

(24)

60

riders

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Cycling Collection by

Martina T.🎈

Tips from the Community

cello_bello
May 14, 2026, Scenic Road Between San Quirico d'Orcia and Pienza

pretty here, very pretty

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pretty here, very pretty

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The Pieve dei Santi Vito e Modesto in Corsignano is a Romanesque church located in the ancient village of Corsignano, today known as Pienza. Its origins date back to the Early Middle Ages and it represents one of the oldest religious buildings in the area.

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La Fattoria Poggio Manzuoli is known for its rows of cypresses and hilly landscape. Some scenes from Ridley Scott's film Gladiator were shot in this area, where the protagonist crosses the fields towards the house. Today it is a popular spot for visitors and photography and cinema enthusiasts.

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I walked the stretch from Borghetto to Castiglione del Lago (8/9 km) and was a little disappointed that you only see the lake once and... watch out for cyclists coming in the opposite direction.

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Chiesa di Santa Maria Assunta The church, dating to the twelfth century, has a plain rectangular plan with a wall covering in square stones. Outside the massive portal is embellished with decorations, maybe originating from the Abbazia di Sant'Antimo. The gabled bell tower and the vestry are original, too. The apse is crowned with corbels and decorated with suspended arches. On the left side there is another monumental portal whose arch is supported by two columns and contains a decorated shape. The extremely plain interior is lit up by narrow slits, one in the apse.

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Very touristy and no culinary highlights... but it's worth a photo. Also ideal for gravel bikers! More tips for gravel bike adventures in the area at https://graveldeluxe.com or in my Komoot profile: https://www.komoot.de/user/graveldeluxe

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Also ideal for gravel bikers! More tips for gravel bike adventures in the area at https://graveldeluxe.com or in my Komoot profile https://www.komoot.de/user/graveldeluxe

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Frequently Asked Questions

How many touring cycling routes are available around Montepulciano?

There are over 100 touring cycling routes around Montepulciano, catering to various skill levels. You'll find a good mix, with about 7 easy routes, 43 moderate routes, and 59 more challenging options for experienced cyclists.

What is the best time of year for touring cycling in Montepulciano?

The ideal time for touring cycling in Montepulciano is generally from March to October. During the warmer summer months, it's advisable to plan your rides for early morning to avoid the midday heat.

What kind of terrain can I expect on touring cycling routes in Montepulciano?

The terrain around Montepulciano is characterized by rolling hills, expansive vineyards, and ancient olive groves. You'll frequently encounter iconic cypress-lined roads and the famous 'strade bianche' (white gravel roads). Routes feature both asphalt and dirt roads, offering diverse surfaces for mountain bikes, road bikes, and e-bikes.

What do other touring cyclists say about the routes in Montepulciano?

The touring cycling routes in Montepulciano are highly regarded by the komoot community, holding an average rating of 4.5 stars from over 250 reviews. More than 1900 touring cyclists have used komoot to explore the region, often praising the stunning panoramic views and the unique Tuscan countryside.

Are there touring cycling routes suitable for beginners or less experienced cyclists in Montepulciano?

Yes, there are routes suitable for beginners. While many routes involve significant elevation, you can find easier options. For example, the Castiglione del Lago loop from Petrignano is a moderate 31.9 km route with less elevation gain, offering a more relaxed experience.

What natural features and landscapes will I encounter on touring cycling routes around Montepulciano?

Cycling in Montepulciano offers breathtaking views of the Val d'Orcia and Val di Chiana, both renowned for their picturesque beauty. You'll see expansive vineyards, olive groves, and distant views of the Monte Amiata volcano. Some routes also feature unique geological formations like the Balze, stratified tuff cliffs, and wetlands near Lago di Chiusi.

What historical towns or cultural sites can I visit while cycling in the Montepulciano area?

Many routes connect Montepulciano with charming historical towns. You can cycle to Pienza, known as the 'ideal Renaissance town,' or the medieval village of Monticchiello. Chianciano Terme, famous for its thermal baths, is also accessible. Within Montepulciano, explore the Piazza Grande and the Temple of San Biagio. The 'Nobile Trail' specifically winds through the vineyards of Vino Nobile di Montepulciano DOCG, offering an immersive wine experience.

Are there any circular touring cycling routes around Montepulciano?

Yes, many touring cycling routes in the area are circular, allowing you to start and end in the same location. An example is the Montepulciano and its cypresses — Ring tour, a 22.1 km route that offers a scenic loop through the Tuscan countryside.

Are there any specific touring cycling routes that offer great viewpoints of Montepulciano or the surrounding area?

Absolutely. The region is full of panoramic vistas. The Overview over Montepulciano – View of Monte Amiata loop from Montepulciano is a moderate 19.4 km route specifically designed to offer stunning views of Montepulciano and the distant Monte Amiata volcano.

Can I find routes that pass by castles or other historical landmarks?

Yes, several routes will take you past historical landmarks. For instance, you might encounter Spedaletto Castle or Rocca del Leone in Castiglione del Lago. The medieval town of Trequanda, with its Cacciaconti Castle, is also part of some routes, offering a glimpse into the region's rich history.

Are there any touring cycling routes that connect Montepulciano with Pienza?

Yes, connecting Montepulciano with Pienza is a popular option for touring cyclists. The Monticchiello – Pienza loop from Montepulciano is a challenging 45 km route that takes you through charming medieval villages and offers expansive views of the Val d'Orcia, including Pienza.

What is the 'Nobile Trail' and where can I find more information about it?

The 'Nobile Trail' is a specific cycling route designed to wind through the vineyards of Vino Nobile di Montepulciano DOCG, offering an immersive experience into the region's winemaking heritage. You can find more information about this trail on the Visit Tuscany website: The Nobile Trail in Montepulciano.

Are there any routes that offer views of Lake Trasimeno?

While Montepulciano is inland, some routes or nearby attractions can lead you towards Lake Trasimeno. The Lakeside Cycle Path – Loop around Lake Trasimeno is a notable highlight for cyclists interested in exploring the lake area, which is accessible from the broader region.

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