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Italy
Tuscany
Siena
Pienza

Pienza, Montepulciano, and Lake Montepulciano Loop

Routes
Bike touring routes & trails
Italy
Tuscany
Siena
Pienza

Pienza, Montepulciano, and Lake Montepulciano Loop

Hard

4.8

(4)

13

riders

Pienza, Montepulciano, and Lake Montepulciano Loop

04:17

58.2km

960m

Cycling

This difficult 36.1-mile touring bicycle ring tour from Pienza to Lake Montepulciano offers challenging terrain and stunning Val d'Orcia vie

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

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1

224 m

Pienza

Highlight • Settlement

A medieval city, awarded by UNESCO as a World Heritage Site. You can enjoy some old churches and palaces here or simply stroll through the atmospheric streets. Also the view from the city wall is great.

Translated by Google •

Tip by

2

7.26 km

View of Montepulciano and the Val d'Orcia

Highlight (Segment) • Viewpoint

Steep gravel. Just not made for the racing bike!

Translated by Google •

Tip by

3

14.7 km

Montepulciano

Highlight • Settlement

A high-altitude medieval and very well-preserved town. Despite the steep ascent, it is highly recommended and worth seeing. Even the view of the town on the approach is magnificent, and …

Showing Translation

Tip by

4

28.6 km

The Montepulciano Lake Regional Nature Reserve is an oasis of tranquility and beauty. Here, you can admire various species of both resident and migratory birds. The dense reed bed on the western shore creates a highly evocative aquatic environment.

Translated by Google •

Tip by

B

58.2 km

End point

Parking

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Way Types & Surfaces

Way Types

39.7 km

7.18 km

4.49 km

4.39 km

2.44 km

Surfaces

40.2 km

8.74 km

5.42 km

3.67 km

166 m

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Elevation

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

Highest point (580 m)

Lowest point (250 m)

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Weather

Powered by Foreca

Wednesday 11 November

18°C

14°C

98 %

Additional weather tips

It’s set to rain on your activity. Pack a waterproof jacket.

to get more detailed weather forecasts along your route

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This route was planned by komoot.

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Frequently Asked Questions

What is the difficulty level of the From Pienza to Lake Montepulciano — Ring tour?

This ring tour is classified as a difficult bike ride, requiring very good fitness. It features significant elevation gain and includes some unpaved, challenging segments where you might need to push your bike.

What kind of terrain can I expect on this cycling route?

The route features a varied terrain, including a mix of paved roads, dirt roads, and gravel sections, famously known as 'strade bianche'. You will encounter rolling hills and valleys, contributing to substantial elevation changes.

What are the main points of interest along the way?

The tour connects several culturally rich locations and offers stunning views. You'll pass through the Renaissance village of Pienza, the historic hilltop town of Historic Center of Montepulciano, and the Lago di Montepulciano Nature Reserve. You'll also enjoy panoramic views, including a View of Montepulciano and the Val d'Orcia.

What is the best time of year to cycle this route?

The Val d'Orcia region is beautiful year-round, but spring (April-May) and autumn (September-October) generally offer the most pleasant cycling conditions with milder temperatures and vibrant landscapes. Summer can be very hot, making the challenging climbs more demanding.

Are there any permits or entrance fees required for this tour?

No specific permits are required to cycle this route. While the tour passes through the Lago di Montepulciano Nature Reserve, there are typically no entrance fees for general access to the cycling paths within the reserve.

Where can I park my car to start the tour?

You can typically find parking in or around the towns of Pienza or Montepulciano, which serve as excellent starting points for this ring tour. Look for designated public parking areas in these towns.

Is the From Pienza to Lake Montepulciano — Ring tour suitable for dogs?

While dogs are generally allowed on trails in the Val d'Orcia, this particular route is a challenging cycling tour. If you plan to bring a dog, ensure it is accustomed to long distances and varied terrain, and always keep it on a leash, especially near roads and in nature reserve areas.

Does this route intersect with other well-known trails?

Yes, this route shares sections with several other paths, including the Cammino d'Assisi, Barlettaia, EuroVelo 7 - Sun Route - part Italy 2, and the Sentiero della Via Barlettaia, among others.

What kind of scenery can I expect while cycling?

You'll experience the iconic landscapes of the Val d'Orcia, a UNESCO World Heritage site. Expect breathtaking panoramic views of rolling hills, cypress-lined roads, vineyards producing Vino Nobile di Montepulciano, and charming Tuscan farmhouses. Some areas were even filming locations for movies like 'Gladiator'.

Are there opportunities for food and wine tastings along the route?

Absolutely. The region is renowned for its gastronomic culture. Both Pienza and Montepulciano offer excellent opportunities for food and wine tastings, including local pecorino cheese in Pienza and Vino Nobile di Montepulciano in Montepulciano, with options to visit underground cellars.

What should I pack for this challenging cycling tour?

Given the difficulty and varied terrain, it's essential to pack appropriate cycling gear, including a helmet, repair kit, sufficient water, snacks, and weather-appropriate clothing. Consider a mountain bike or a sturdy touring bike suitable for gravel sections. Don't forget your camera for the stunning views!

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