4.8
(13)
384
riders
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
Start point
Parking
Get Directions
22.7 km
Highlight • Monument
Translated by Google •
Tip by
24.8 km
Highlight (Segment) • Trail
Translated by Google •
Tip by
51.9 km
Highlight • Bridge
Translated by Google •
Tip by
74.7 km
End point
Parking
Way Types & Surfaces
Way Types
38.4 km
35.7 km
458 m
160 m
Surfaces
73.9 km
731 m
160 m
Sign up to see more specific route details
Sign up for free
Elevation
Highest point (580 m)
Lowest point (100 m)
Sign up to see more specific route details
Sign up for free
Weather
Powered by Foreca
Tuesday 26 May
34°C
18°C
0 %
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.
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.
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.
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.
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.
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.
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.
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%).
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.
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.
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.
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.
Last lap in this beautiful area for 2021 I'll be back in 2022 ’
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 😁