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Routes
Road cycling routes
Italy
Tuscany
Siena

Chianti Classico Loop

Hard

4.8

(13)

384

riders

Chianti Classico Loop

03:35

74.7km

1,010m

Road cycling

Embark on the Chianti Classico Loop for a challenging road cycling experience through the heart of Tuscany. This difficult route spans 46.4 miles (74.7 km) and features a significant elevation gain of 3317 feet (1011 metres), offering you classic Tuscan landscapes. You will ride past rolling hills, endless vineyards, and…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

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1

22.7 km

Black Rooster Statue, Castellina in Chianti

Highlight • Monument

Castellina in Chianti is located in the province of Siena, in the Chianti Classico area. He is easily accessible from the Elsa Valley, Arbiatal and Pesatal. Due to the altitude, …

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2

24.8 km

If you are looking for a scenic, low-traffic and relaxed road up to Castellina in Chianti you will find it here.
On the approximately 18 kilometers with 450 meters of …

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3

51.9 km

Bridge over the Elsa River

Highlight • Bridge

Beautiful crossing on the Elsa River. If you have time there is a path that leads from the bridge to the river where it is pleasant to dip your feet in the summer! A little further on the Diborrato waterfalls!

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74.7 km

End point

Parking

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Way Types & Surfaces

Way Types

38.4 km

35.7 km

458 m

160 m

Surfaces

73.9 km

731 m

160 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 (100 m)

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Weather

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Tuesday 26 May

34°C

18°C

0 %

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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 difficulty level of this racebike tour?

This tour is rated as difficult. The terrain around Castellina in Chianti features rolling hills with significant ascents and descents. It requires at least average athletic preparation, and some segments involve steep climbs of medium intensity.

Is this racebike tour suitable for beginners?

No, given its 'difficult' rating, significant distance of approximately 74.7 km, and over 1000 meters of elevation gain, this tour is not recommended for beginners. It requires good physical fitness and experience with road cycling on hilly terrain.

What kind of terrain can I expect on this route?

The route primarily features rolling hills with a mix of ascents and descents. For racebikes, you can expect mostly fully paved, well-maintained roads with low vehicle traffic. However, be aware that some broader Chianti routes can include 'strade bianche' (dirt or gravel sections), so choosing the right route is key to ensure it's predominantly asphalt for racebikes.

Where does the Castellina in Chianti — Ring tour start and where can I park?

The tour is a ring tour, meaning it starts and ends in the same location, typically Castellina in Chianti. While specific parking details for this exact route aren't provided, Castellina in Chianti offers various public parking options within or near the town center, which can serve as a convenient starting point.

What are the best times of year to cycle this route?

The best times to cycle in the Chianti region are generally spring (April-May) and autumn (September-October). During these seasons, the weather is typically mild, and the landscapes are vibrant with blooming flowers or autumn colors. Summer can be very hot, and winter might bring colder temperatures and less predictable weather.

What notable sights will I see along the way?

Along the route, you'll encounter classic Tuscan landscapes, including vineyards, olive groves, and picturesque medieval villages. Specific highlights include the Black Rooster Statue in Castellina in Chianti, a Scenic Road from Poggibonsi to Castellina in Chianti, and a Bridge over the Elsa River. You'll also cycle through the heart of the Chianti Classico wine region.

Does this route intersect with other well-known cycling paths?

Yes, this route overlaps with several other official trails. Notable intersections include sections of the EuroVelo 5 - Via Romea Francigena - part Italy (26% of the route), Ciclovia Francigena - VFB16 (22%), and Via Romea Sanese - Tappa 4 (16%).

Are dogs allowed on this racebike tour?

This is a road cycling tour primarily on public roads. While there are no specific restrictions against dogs on public roads, bringing a dog on a racebike tour of this length and difficulty is generally not practical or safe. If you plan to bring a dog, consider shorter, less strenuous routes or alternative modes of transport.

Do I need any permits or pay entrance fees for this tour?

No, you do not need any special permits or pay entrance fees to cycle this route, as it primarily uses public roads through the Chianti region. However, if you plan to visit specific attractions or wineries along the way, they may have their own entry fees.

Are there places to stop for food and water along the route?

Yes, as the route passes through several towns and villages in the Chianti region, you will find opportunities to stop for food, water, and coffee. Castellina in Chianti itself offers various cafes and restaurants. It's always wise to carry sufficient water and snacks, especially between villages.

What makes cycling in the Castellina in Chianti area special?

Cycling here offers an authentic Tuscan experience. You're in the heart of the Chianti Classico wine region, surrounded by historic villages, ancient castles, and endless vineyards. The low-traffic, well-maintained roads allow for an immersive journey through stunning landscapes, combining physical activity with cultural and culinary appreciation.

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Trail Reviews

awiengarn
October 8, 2021, 🇮🇹_Fonterutoli-Monteriggione Runde 💨💨💨🚴‍♂️

Last lap in this beautiful area for 2021 I'll be back in 2022 ’

Translated by Google

Shouldn't rain until late afternoon so at least did a medium lap. After a bit of getting lost, it first went to Poggibonsi, a nice slalom around numerous potholes, and then further east, steadily and moderately uphill to Castellina. I haven't had that much uphill at a time for a long time. But it was really great, with a breather and photo breaks🙂 The view of the vines, olive trees and blossoms everywhere was fantastic, it cleared up after Castellina (extra for me haha) but the ride was rather chilly and I was thankful for long-long. In the meantime, I've been cheered on by Italian gentlemen (in the tractor) from time to time. Cute. Back just before the rain, hungry enough to extend the half-board from 3 to 4 courses. Of course there had to be a glass of Chianti 😁

Translated by Google
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