Routes

Planner

Features

Updates

App

Get the App

Siena

Siena

The best cycling routes in Siena

4.5

(5164)

69,938

riders

2,323

rides

Cycling in Siena is one of the most enjoyable ways to explore more of this part of Tuscany. So you can find your perfect Siena bike ride, we’ve reviewed our full collection of cycling routes in the region to deliver the best. Just click on each route to see a full breakdown of detailed information including elevation profiles and surface analyses, and browse real tips and photos uploaded by other members of the komoot community.

Last updated: October 23, 2025

4.7

(36)

186

riders

1. Bagno Vignoni, Pienza e San Quirico d'Orica — Round trip

24.6km

02:02

470m

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

Navigate

Send to Phone

Save

Expert

4.8

(8)

201

riders

2. From Siena to Castellina in Chianti – loop tour

68.3km

04:41

1,140m

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

Navigate

Send to Phone

Save

Expert

Let us show you the way with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures in England and beyond.

4.8

(11)

189

riders

3. From Siena to Asciano – loop tour

71.6km

04:45

940m

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

Navigate

Send to Phone

Save

Expert

4.7

(15)

163

riders

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

58.2km

03:58

770m

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

Navigate

Send to Phone

Save

Expert

4.3

(28)

130

riders

5. From Colle Val d’Elsa to San Gimignano

37.5km

02:48

730m

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

Navigate

Send to Phone

Save

Expert

4.4

(22)

190

riders

6. From Buonconvento to Montalcino — Round trip

35.2km

03:11

710m

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

Navigate

Send to Phone

Save

Expert

4.2

(23)

riders

7. The colors of Chianti — Ring tour

27.2km

02:14

490m

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

Navigate

Send to Phone

Save

Expert

4.5

(20)

136

riders

8. From Siena to Monteriggioni and Gracciano d'Elsa

53.1km

03:42

670m

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

Navigate

Send to Phone

Save

Expert

4.8

(5)

143

riders

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

59.1km

04:02

1,010m

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

Navigate

Send to Phone

Save

Expert

4.9

(13)

127

riders

10. Abbazia di Sant'Antimo and Castelnuovo dell’Abate from Montalcino – gravel loop tour

27.4km

02:09

520m

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

Navigate

Send to Phone

Save

Expert

Get access to more routes and recommendations from other explorers.

Already have an account?

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

Other adventures in Siena

Ciclovia dei due mari - By bike from the Tyrrhenian Sea to the Adria

Cycling Collection by

BeCycling

Villages, iconic roads and vineyards – Grand Tour of Chianti

Cycling Collection by

Francesco | Cyclo Ergo Sum

Cycling between Siena and Cortona – la Via Lauretana in Tuscany

Cycling Collection by

Francesco | Cyclo Ergo Sum

L'Eroica di Gaiole in Chianti

Cycling Collection by

Nicola Amadini

Bike ride through the Elysian Fields – Eroica Montalcino

Cycling Collection by

Nicola Amadini

Iconic dirt roads in Italy’s Tuscan hills – Strade Bianche

Cycling Collection by

Nicola Amadini

Cycling route through Tuscany – Grand Tour of Val di Merse

Cycling Collection by

Emiliano Manzan

Tuscany by bike — nine Tours for every taste

Cycling Collection by

Toscana

Most popular routes in Siena

Road Cycling Routes in Siena

Hiking in Siena

Easy hikes in Siena

MTB Trails in Siena

Running Trails in Siena

Gravel biking in Siena

Waterfall hikes in Siena

Most popular attractions in Siena

Places to see

Natural Monuments

Castles

Mountain Peaks

Lakes

Bike Parks

Waterfalls

Caves

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures around London and beyond.

Join komoot Now

Didn’t find what you were looking for?

Check out more 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 Cycling routes in other regions.

Grosseto Lucca Florence Prato Arezzo Pisa Massa-Carrara Pistoia

The best cycling routes in Siena

1. Bagno Vignoni, Pienza e San Quirico d'Orica — Round trip

2. From Siena to Castellina in Chianti – loop tour

3. From Siena to Asciano – loop tour

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

5. From Colle Val d’Elsa to San Gimignano

6. From Buonconvento to Montalcino — Round trip

7. The colors of Chianti — Ring tour

8. From Siena to Monteriggioni and Gracciano d'Elsa

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

10. Abbazia di Sant'Antimo and Castelnuovo dell’Abate from Montalcino – gravel loop tour

Other adventures in Siena

Most popular routes in Siena

Most popular attractions in Siena

Get inspired with the komoot mobile app

Didn’t find what you were looking for?

Explore more

Get ready to conquer new peaks

We value your privacy ⛰️

We value your privacy ⛰️