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San Casciano In Val Di Pesa

Chianti Loop: San Casciano, Greve, and Panzano

Moderate

4.5

(12)

169

riders

Chianti Loop: San Casciano, Greve, and Panzano

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

A

Start point

Parking

Get Directions

1

7.28 km

Scenic Road from Panzano in Chianti to Le Quattro Strade

Highlight (Segment) • Cycleway

In Panzano in Chianti, the SP118 branches off to the north. In constant ups and downs, it is a ridge road with almost continuous great views in both directions, west …

Translated by Google •

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2

20.6 km

Panzano in Chianti Village

Highlight • Settlement

Panzano in Chianti is like many villages on a hill and therefore offers a nice view.
For us racing cyclists, it also means the highest point of, in this case, …

Translated by Google •

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3

27.0 km

Greve in Chianti

Highlight • Settlement

Greve in Chianti is one of the bigger places in the Chianti area. Therefore also quite touristically developed.
Piazza Matteotti, the main square in the town, has an interesting, triangular …

Translated by Google •

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B

49.7 km

End point

Parking

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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

Elevation

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

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.

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Frequently Asked Questions

How long does it typically take to complete this cycling loop?

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.

What is the terrain like on this Chianti cycling route?

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.

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

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.

Where can I park to start this cycling loop?

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.

What are the main villages and points of interest along the loop?

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.

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

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.

Is this cycling route dog-friendly?

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.

Are there places to refill water or get refreshments along the way?

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.

Does this route connect with other cycling paths?

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.

Is this route suitable for beginners?

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.

What should I bring for a racebike ride on this loop?

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.

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