Chianti Loop: San Casciano, Greve, and Panzano
Chianti Loop: San Casciano, Greve, and Panzano
4.5
(12)
169
riders
02:26
49.7km
730m
Road cycling
This moderate 30.9-mile road cycling loop from San Casciano explores the scenic vineyards and charming villages of Chianti Classico.
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
7.28 km
Highlight (Segment) • Cycleway
Translated by Google •
Tip by
20.6 km
Highlight • Settlement
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Tip by
27.0 km
Highlight • Settlement
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Tip by
49.7 km
End point
Parking
Way Types & Surfaces
Way Types
34.0 km
15.5 km
113 m
< 100 m
< 100 m
Surfaces
49.6 km
< 100 m
< 100 m
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Elevation
Highest point (530 m)
Lowest point (110 m)
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Weather
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Monday 25 May
34°C
16°C
0 %
Additional weather tips
Max wind speed: 5.0 km/h
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This route was planned by komoot.
This moderate racebike loop, covering approximately 49.7 km (30.9 miles) with about 734 meters (2,395 feet) of elevation gain, typically takes around 2 hours and 25 minutes of active cycling time. However, allow extra time to enjoy the charming villages and scenic viewpoints.
The route primarily features well-paved roads, ideal for racebikes. Be prepared for typical Tuscan 'ups and downs,' including alternating steep ramps and descents. While mostly paved, some segments might have rougher asphalt, particularly on roads like the SP118 from Panzano. You'll traverse rolling hills adorned with vineyards and olive groves.
The best times to cycle in Chianti are generally spring (April-May) and autumn (September-October). During these seasons, the weather is pleasant, and the landscape is particularly beautiful, with blooming flowers or vibrant autumn colors. Summers can be very hot, and winters might be chilly and wet.
The loop starts from San Casciano. You can find parking in or around San Casciano Val di Pesa. Look for public parking areas within the town, which often have free or metered options, especially near the town center or on its outskirts.
This route connects several significant Chianti towns and offers numerous sights. You'll pass through Panzano in Chianti Village, known for its stunning views and Dario Cecchini's butcher shop, and Greve in Chianti, the 'heart of Chianti Classico' with its famous Piazza Mercatale. Other notable stops include the Romanesque Parish Church of San Cresci and the medieval village of Montefioralle.
No, you do not need any special permits or pay entrance fees to cycle this route. The roads are public, and there are no specific regulations for cyclists beyond standard traffic laws. The Chianti Classico region is open for exploration.
While the route itself is on public roads, which are generally accessible, it's not specifically designed for dogs. If you plan to bring a dog, ensure they are comfortable with being in a bike trailer or are able to keep pace safely. Always keep dogs on a leash when off the bike, especially in villages or near traffic.
Yes, both Panzano in Chianti Village and Greve in Chianti offer numerous cafes, restaurants, and shops where you can refill water bottles, grab a coffee, or enjoy local Tuscan dishes and Chianti Classico wine. It's advisable to carry sufficient water, especially during warmer months.
Yes, this route briefly intersects with sections of several other paths. You'll find short overlaps with trails such as Anello Montefioralle, Anello di Calcinaia, Anello di Uzzano, and the Via Romea Del Chianti.
This loop is classified as 'moderate' and requires good fitness due to its significant elevation gain and alternating steep ramps. While not extreme, it's not ideal for absolute beginners to road cycling. Riders should be comfortable with ascents and descents and have a reasonable level of endurance.
For this racebike loop, bring your helmet, appropriate cycling attire, sufficient water, and snacks. A repair kit (spare tube, pump, tire levers) is highly recommended. Given the hilly terrain, consider gearing suitable for climbing. Don't forget your camera for the stunning Chianti views, especially along the Scenic Road from Panzano in Chianti to Le Quattro Strade.