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Siena

Siena

The best road cycling routes in Siena

4.6

(1717)

62,900

riders

1,224

rides

In this guide, we’ve reviewed our full collection of road biking routes in Siena to bring you the best rides in the region. To find the one which is right for you, click on any of the Tours to see a full breakdown of its details including elevation profiles and surface analyses, and browse real tips and photos shared by other members of the Komoot community.

Last updated: October 19, 2025

4.7

(7)

4,304

riders

1. GF White Roads — Ring tour

144km

09:55

2,220m

Expert road ride. Very good fitness required. You may need to push your bike for some segments of this route.

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4.4

(26)

573

riders

2. Strade Bianche di Siena e Asciano — Round trip

63.1km

03:27

980m

Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

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4.9

(27)

742

riders

3. From Siena to Castellina in Chianti – loop tour

64.4km

03:07

960m

Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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4.9

(12)

377

riders

4. From Siena to Passo dell'Incrocati – loop tour

56.2km

03:00

1,000m

Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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4.8

(13)

345

riders

5. Castellina in Chianti — Ring tour

74.7km

03:35

1,010m

Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

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4.6

(16)

288

riders

6. From Montalcino to Montepulciano – loop tour

79.4km

03:59

1,300m

Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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4.3

(11)

249

riders

7. From Siena to Monteroni d'Arbia and Asciano – loop tour

76.6km

03:48

1,080m

1,070m

Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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4.2

(6)

326

riders

8. Strade Bianche Bagnaia e Vidritta da Siena – loop tour

55.0km

02:59

720m

Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Intermediate

4.7

(17)

255

riders

9. Around San Gimignano — Ring tour

40.3km

02:11

730m

Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Intermediate

4.2

(9)

260

riders

10. From Montalcino to Castiglione d'Orcia – loop tour

50.2km

02:46

1,090m

Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Didn’t find what you were looking for?

Check out more Road cycling 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 Road cycling routes in other regions.

Lucca Florence Grosseto Arezzo Massa-Carrara Prato Pisa Pistoia

The best road cycling routes in Siena

1. GF White Roads — Ring tour

2. Strade Bianche di Siena e Asciano — Round trip

3. From Siena to Castellina in Chianti – loop tour

4. From Siena to Passo dell'Incrocati – loop tour

5. Castellina in Chianti — Ring tour

6. From Montalcino to Montepulciano – loop tour

7. From Siena to Monteroni d'Arbia and Asciano – loop tour

8. Strade Bianche Bagnaia e Vidritta da Siena – loop tour

9. Around San Gimignano — Ring tour

10. From Montalcino to Castiglione d'Orcia – loop tour

Other adventures in Siena

Most popular routes in Siena

Most popular attractions in Siena

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