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Running trails & routes
Italy
Tuscany
Siena
Pienza

Pienza - Way of Assisi Loop

Moderate

6

runners

Pienza - Way of Assisi Loop

00:41

5.54km

180m

Running

Jogging the Pienza - Way of Assisi Loop offers a moderate 3.4-mile route through the scenic Val d'Orcia, with 591 feet of gain.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

Get Directions

1

494 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

2.04 km

Gladiator Road, Val d'Orcia

Highlight • Viewpoint

What has made this area famous are the films, many directors have chosen this wonderful natural environment to shoot very important films, including "Gladiator", set right in Pienza.

Translated by Google •

Tip by

3

2.42 km

The symbol of this area of Tuscany are undoubtedly the many cypresses that frame the fairytale setting.

Translated by Google •

Tip by

B

5.54 km

End point

Parking

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Way Types & Surfaces

Way Types

3.09 km

1.66 km

778 m

Surfaces

1.95 km

1.34 km

1.27 km

489 m

394 m

< 100 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 (490 m)

Lowest point (310 m)

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Weather

Powered by Foreca

Monday 18 May

20°C

7°C

52 %

Additional weather tips

Max wind speed: 16.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the terrain like on the Pienza - Way of Assisi Loop?

The route around Pienza features varied terrain. You can expect a mix of paved surfaces and unpaved gravel roads, known locally as 'strade bianche'. While generally suitable for jogging, some sections might require good fitness and sure-footedness, especially on the gravel parts.

Is this trail suitable for beginners?

Rated as 'moderate' with an elevation gain of about 180 meters over 5.5 kilometers, this loop is suitable for joggers with a reasonable level of fitness. Beginners might find some of the uphill sections challenging but manageable with breaks.

What can I see along the Pienza - Way of Assisi Loop?

This loop offers stunning views of the Val d'Orcia, a UNESCO World Heritage site. You'll pass through picturesque rolling hills, cypress trees, vineyards, and olive groves. Key sights include the charming town of Pienza itself, the iconic Gladiator Road, Val d'Orcia, and the beautiful Cypress Lined Paths of Val d'Orcia.

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

Spring (April-May) and Autumn (September-October) are ideal. The weather is milder, and the landscape is particularly vibrant with wildflowers in spring or rich autumnal colors. Summer can be very hot, making early morning or late afternoon jogs preferable, while winter can bring colder temperatures and potentially muddy conditions on unpaved sections.

Is the Pienza - Way of Assisi Loop dog-friendly?

Yes, dogs are generally welcome on trails in the Val d'Orcia region. However, it's always best to keep your dog on a leash, especially when passing through agricultural areas, near livestock, or in populated sections of Pienza. Remember to bring water for your pet.

Do I need a permit or pay an entrance fee for this trail?

No, there are no specific permits or entrance fees required to jog this loop. The trails are publicly accessible, allowing you to enjoy the natural beauty of the Val d'Orcia freely.

Where does the Pienza - Way of Assisi Loop start, and is there parking available?

The Komoot tour for this loop typically starts and ends in Pienza. Parking is available in and around the town, often in designated parking lots just outside the historic center. Arriving earlier in the day, especially during peak season, can help secure a spot.

Does this route intersect with other well-known paths?

Yes, this route utilizes sections of several other paths. You'll find yourself on parts of the Cammino d'Assisi, Bagno Vignoni - Pienza, Sentiero della Via Barlettaia, and Strada di Terrapille, among others, as you complete the loop.

What should I bring for jogging this loop?

Given the varied terrain and moderate difficulty, we recommend wearing appropriate jogging shoes suitable for both paved and gravel surfaces. Bring water, especially on warmer days, and consider a hat and sunscreen. A small backpack for essentials like snacks, a phone, and a light jacket (depending on the season) is also advisable.

Are there any cafes or places to rest along the way?

The loop starts and ends in Pienza, where you'll find numerous cafes, restaurants, and shops to refuel and relax before or after your jog. There are no specific facilities directly on the trail itself, so plan accordingly.

What makes the Val d'Orcia unique for jogging?

The Val d'Orcia, where this loop is located, is a UNESCO World Heritage site renowned for its iconic Tuscan landscape. Jogging here offers a unique blend of sport, nature, and culture, allowing you to experience the region's beauty, from its cypress-lined paths to its medieval villages, in an active way. It's a landscape that has inspired artists and even served as a backdrop for films like 'Gladiator'.

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