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Siena

Siena

The best running trails in Siena

4.3

(468)

12,918

runners

1,142

runs

Running in Siena is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full collection of routes in Siena—and are proud to present the best running trails. Click on any of the routes for more details and browse real tips and photos uploaded by other runners.

Last updated: October 14, 2025

5.0

(1)

173

runners

1. From Montalcino to Castel Abbate − loop tour

26.1km

03:16

810m

Expert run. Very good fitness required. Mostly accessible paths. Some sure footedness required.

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Expert

3.7

(12)

109

runners

2. The Strada dei Capuccini from Parco San Prospero – loop tour

7.82km

00:50

90m

100m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

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5.0

(1)

116

runners

3. Between Montalcino and Poggio Civitella − loop tour

14.9km

01:49

390m

Expert run. Very good fitness required. Mostly accessible paths. Some sure footedness required.

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Expert

4.6

(7)

runners

4. Strada delle Tolfe from Basilica dell'Osservanza – loop trail

8.15km

00:53

130m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

3.5

(4)

runners

5. Parco Unità d'Italia from Petriccio – loop tour

9.00km

00:58

150m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

4.6

(10)

runners

6. The cypresses of San Quirico d'Orcia — Ring tour

9.86km

01:09

210m

Intermediate run. Good fitness required. Mostly accessible paths. Some sure footedness required.

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Intermediate

4.5

(2)

runners

7. Diga di Monaciano e Certosa di Pontignano – loop tour

7.83km

00:54

140m

Intermediate run. Good fitness required. Mostly accessible paths. Some sure footedness required.

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5.0

(2)

runners

8. The River Park of the high Val D'Elsa — Ring tour

4.94km

00:33

30m

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

runners

9. Pienza and its cypresses — Ring tour

5.54km

00:41

180m

Intermediate run. Good fitness required. Mostly accessible paths. Some sure footedness required.

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Intermediate

runners

10. Monteliscai and Colle Pinzuto – loop tour

12.7km

01:26

230m

Intermediate run. Good fitness required. Mostly accessible paths. Some sure footedness required.

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Intermediate

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Didn’t find what you were looking for?

Check out more Running Trails & Routes throughout Siena below and find the perfect route in your destination.

Chiusi Chiusdino Radda In Chianti Piancastagnaio Torrita Di Siena Asciano Riserva Naturale Di Castelvecchio Casole D'Elsa Riserva Naturale Pigelleto Lake Chiusi Sinalunga Montalcino Colle Di Val D'Elsa Poggibonsi Montepulciano Trequanda Riserva Naturale Del Bosco Di Sant'Agnese San Quirico D'Orcia Gaiole In Chianti Castiglione D'Orcia Sarteano Radicondoli Monteroni D'Arbia San Giovanni D'Asso Chianciano Terme Buonconvento Abbadia San Salvatore Lago di Montepulciano Monteriggioni Monticiano Sovicille Radicofani Pienza Murlo Rapolano Terme Cetona Riserva Naturale Crete Dell'Orcia Riserva Naturale Lucciola Bella Riserva Naturale Lago di Montepulciano Riserva Naturale Cornate E Fosini Riserva Naturale Il Bogatto Riserva Naturale Basso Merse Castellina In Chianti San Gimignano San Casciano Dei Bagni Riserva Naturale Alto Merse Castelnuovo Berardenga Riserva Naturale Pietraporciana

Explore more

Browse the best Running Trails & Routes in other regions.

Lucca Grosseto Florence Pisa Arezzo Massa-Carrara Prato Pistoia

The best running trails in Siena

1. From Montalcino to Castel Abbate − loop tour

2. The Strada dei Capuccini from Parco San Prospero – loop tour

3. Between Montalcino and Poggio Civitella − loop tour

4. Strada delle Tolfe from Basilica dell'Osservanza – loop trail

5. Parco Unità d'Italia from Petriccio – loop tour

6. The cypresses of San Quirico d'Orcia — Ring tour

7. Diga di Monaciano e Certosa di Pontignano – loop tour

8. The River Park of the high Val D'Elsa — Ring tour

9. Pienza and its cypresses — Ring tour

10. Monteliscai and Colle Pinzuto – loop tour

Other adventures in Siena

Most popular routes in Siena

Most popular attractions in Siena

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