Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Bike touring routes & trails
Italy
Tuscany
Siena

L'Eroica Chianti Loop from Siena

Hard

4.8

(8)

218

riders

L'Eroica Chianti Loop from Siena

04:41

68.3km

1,140m

Cycling

Cycle the difficult 42.5-mile L'Eroica Chianti Loop from Siena, featuring white gravel roads, vineyards, and Tuscan scenery.

Last updated: February 26, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions. Check ahead to confirm restricted segments are open to the public.

After 19.4 km for 276 m

Waypoints

A

Start point

Parking

Get Directions

1

14.6 km

Fonterutoli

Highlight • Settlement

Fonterutoli, during the wars between Siena and Florence, was the site of the agreements that put an end to the dispute over the Chianti territories. It is said that the …

Translated by Google •

Tip by

2

16.9 km

Panoramic view of Siena and Montemaggio

Translated by Google •

Tip by

3

19.4 km

Castellina in Chianti

Highlight • Settlement

Castellina in Chianti is located in the province of Siena, in the Chianti Classico area. Accessible from several valleys, it offers breathtaking views. It is a crucial point for cyclists …

Translated by Google •

Tip by

4

31.3 km

Radda in Chianti

Highlight • Settlement

A walk through the narrow, winding streets and numerous ornate vaulted passages transports you back to bygone medieval times, as if Radda were still the capital of the “Lega del Chianti”.

Translated by Google •

Tip by

5

46.8 km

Climb up to Castello di Brolio

Highlight (Segment) • Climb

Crossing the entrance gate to Brolio Castle, you enter a dirt road that proceeds steeply uphill surrounded by trees.
You can pedal while enjoying the refreshment of the branches that guide you to the 12th century castle.

Translated by Google •

Tip by

6

47.8 km

Brolio Castle

Highlight • Castle

The castle of Brolio, surrounded by the vines that produce the most famous wines in the world. For bicycle lovers it is located on the permanent route of the Eroica, for wine lovers its cellar cannot miss a visit.

Translated by Google •

Tip by

7

52.7 km

Il leccione - secular oak

Highlight • Natural Monument

The "Leccione" is a secular tree and represents an iconic icon of Gaiole in Chianti. With the splendid panorama of Siena in the background, these two majestic holm oaks embrace …

Translated by Google •

Tip by

B

68.3 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

44.7 km

19.5 km

3.59 km

366 m

226 m

Surfaces

64.4 km

3.11 km

625 m

215 m

Sign up to see more specific route details

Sign up for free

Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (620 m)

Lowest point (220 m)

Sign up to see more specific route details

Sign up for free

Weather

Powered by Foreca

Tuesday 12 May

22°C

10°C

67 %

Additional weather tips

Max wind speed: 16.0 km/h

to get more detailed weather forecasts along your route

This route was planned by komoot.

Save

Edit route

Download GPX

Move start point

Print

Share

Embed on a website

Report an Issue

Frequently Asked Questions

How long does it take to cycle the L'Eroica Chianti Loop from Siena?

This specific Komoot route, a challenging loop from Siena, is approximately 68.3 kilometers (42.4 miles) long with about 1140 meters (3740 feet) of elevation gain. For a touring cyclist, it typically takes around 4 to 5 hours to complete, depending on your pace and stops.

What is the terrain like on this Chianti cycling route?

The route offers a classic Tuscan cycling experience, featuring a mix of paved roads and significant stretches of unpaved gravel roads, known as 'strade bianche'. You can expect continuous ups and downs with challenging climbs and descents, winding through vineyards, olive groves, and rolling hills. The gravel sections are a defining feature, requiring good bike handling skills.

What are the main points of interest along the way?

This loop takes you through some beautiful Chianti scenery and charming villages. Highlights include the picturesque settlement of Fonterutoli, a Panoramic View from the Chiantigiana, and the historic towns of Castellina in Chianti and Radda in Chianti. You'll also encounter the Climb up to Castello di Brolio, the impressive Brolio Castle, and the ancient Il leccione - secular oak.

Is this L'Eroica-inspired route suitable for beginners?

No, this route is classified as difficult. While it's shorter than the full L'Eroica permanent route, its significant elevation gain over 68 kilometers and the challenging 'strade bianche' sections require good physical fitness and advanced riding skills. Beginners might find the continuous climbs and gravel surfaces very demanding.

What is the best time of year to cycle this loop?

The best times to cycle this route are spring (April to June) and autumn (September to October). During these seasons, the weather is generally mild and pleasant, and the Tuscan landscape is particularly beautiful. Summer can be very hot, making the climbs more challenging, while winter can bring colder temperatures and potentially wet, muddy gravel roads.

Where can I park my car when starting this loop from Siena?

Siena has several parking options, particularly outside the historic center. Look for public parking lots such as Parcheggio Fortezza-Stadio or Parcheggio Santa Caterina, which are typically well-located for accessing routes leading out of the city. From these, you can easily start your cycling adventure.

Are there any permits or entrance fees required to cycle this route?

No, there are no specific permits or entrance fees required to cycle this public route. The 'strade bianche' and roads are freely accessible. However, if you plan to visit specific attractions like Brolio Castle, there might be separate entrance fees for those sites.

Is the L'Eroica Chianti Loop from Siena dog-friendly?

While the route itself is on public roads and trails where dogs are generally allowed, it's important to consider the nature of the ride. This is a challenging touring bicycle route with significant distance and elevation. Carrying a dog on a bike for this duration and difficulty might not be feasible or comfortable for the animal. If you plan to bring a dog, ensure it's well-trained, accustomed to cycling, and that you have appropriate gear for its safety and comfort.

Does this route intersect with other well-known paths?

Yes, this route shares sections with several other paths. Notably, about 36% of the route overlaps with the official 'L'Eroica' permanent route. Smaller portions also intersect with 'Via Romea Sanese - Tappa 4' (11%) and 'Strade Bianche' (6%), among others.

What kind of bicycle is recommended for this route?

Given the mix of paved and unpaved 'strade bianche' sections, a touring bicycle with robust tires (at least 32mm wide) and good suspension is highly recommended. A gravel bike or a sturdy road bike with wider tires would also be suitable. Standard road bikes with narrow tires might struggle on the gravel sections.

Are there places to eat or refill water along the route?

Yes, the route passes through several charming towns and villages like Castellina in Chianti and Radda in Chianti. These settlements offer opportunities to find cafes, restaurants, and shops where you can purchase food and refill your water bottles. It's always wise to carry enough water and snacks, especially between towns.

Nearby routes

Hard

4.8

218

L'Eroica Chianti Loop from Siena

04:41h

68.3km

1,140m

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy