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Routes

Bike touring routes & trails

Italy

Tuscany

Siena

Castelnuovo Berardenga

Radda in Chianti – The cypresses of Catignano loop from Ponte a Bozzone

Routes

Bike touring routes & trails

Italy

Tuscany

Siena

Castelnuovo Berardenga

Radda in Chianti – The cypresses of Catignano loop from Ponte a Bozzone

Hard

4.0

(4)

riders

Radda in Chianti – The cypresses of Catignano loop from Ponte a Bozzone

03:42

50.9km

850m

Cycling

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: May 12, 2026

Waypoints

Start point

Parking

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2.16 km

View of Siena and Chianti Vineyards

Highlight • Viewpoint

Between Ponte a Bozzone and the splendid Certosa di Pontignano, on the panoramic Via della Certosa you can turn towards Siena to glimpse the distant skyline, with the sensational vineyards of the Chianti area in the foreground. To go slowly letting yourself be enraptured by the panorama.

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10.4 km

Vagliagli

Highlight • Settlement

This is Vagliagli, a suggestive hamlet of Castelnuovo Berardenga, an authentic medieval village located a few kilometers north of Siena, in the enchanting heart of the Chianti area.

Here, time seems to have stopped, and I invite you to walk the ancient paved streets, which lead you into a unique atmosphere of timeless charm and beauty.

But the real inebriating experience of Vagliagli is linked to the local food and wine. Enjoy the typical delicacies of this area, sipping the renowned Chianti wines and delighting yourself with the traditional culinary specialties.
Vagliagli awaits you, ready to give you a dive into the past and a journey of authentic pleasures. Don't miss out on this wonderful experience!

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10.9 km

View of Cypress Trees and Vineyards in Tuscany

Highlight • Viewpoint

11.1 km

Chianti White Road

Highlight (Segment) • Cycleway

In the heart of Chianti, this is one of the typical and very famous white roads. Here you pedal on a pleasant gravel between the iconic hills of Tuscany.

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22.1 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”.

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