Scenic Walks Through Vineyards

from Radda in Chianti to Volpaia and Castelvecchi

Route technical data

• Starting point: Radda in Chianti (530 m a.s.l.)
• Ending point: Castelvecchi (approx. 600 m a.s.l.)
• Total distance: approx. 17–18 km
• Total elevation gain: 600–650 m
• Walking time: 5–6 hours (excluding breaks)
• Difficulty: E – Hiking
• Route type: linear
• Terrain: gravel roads, dirt paths, short paved sections
• Best season: spring and autumn
• Waymarking: partial (GPX track recommended)

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Route description

1. From Radda in Chianti to Volpaia

(approx. 11–12 km | +350–400 m | 3–4 hours)

The first section follows the classic Radda–Volpaia route, crossing gravel roads, vineyards and isolated farmhouses. The elevation profile features continuous gentle ups and downs, with a more sustained climb in the final kilometres before reaching Volpaia.

This section offers wide views over the Chianti Classico hills, with long stretches exposed to the sun.

Volpaia is an excellent intermediate stop thanks to the availability of restaurants and wineries.

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2. From Volpaia to Castelvecchi

(approx. 6–7 km | +250 m | 2–2.5 hours)

Leaving Volpaia, the route continues towards Castelvecchi, following dirt roads and paths that enter a more wooded and quieter environment compared to the previous section.

After exiting the village, the trail alternates between:

• gentle descents through vineyards,
• shaded woodland stretches,
• steady, non-technical climbs leading gradually towards the hills where Castelvecchi is located.

This section is less panoramic but more intimate, with landscapes dominated by oak woods, cypress trees and historic vineyards. In the final kilometres, a gradual ascent leads to the end of the walk.

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Castelvecchi: end of the route

Arrival in Castelvecchi marks the end of an itinerary with strong landscape and historical continuity. This small rural settlement, surrounded by vineyards and rolling hills, represents the quieter and more agricultural side of Chianti.

Services are limited; advance planning for accommodation or return transport is recommended.

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Practical advice

• Water: carry at least 2–2.5 litres per person
• Footwear: hiking boots or trail shoes with good grip
• Navigation: GPS device or GPX track recommended
• Logistics: return by pre-arranged car or local transfer

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Variants and connections

• Possible return to Radda via alternative routes passing through Gaiole in Chianti (for experienced hikers)
• Route can be divided into two stages:
  • Day 1: Radda in Chianti – Volpaia
  • Day 2: Volpaia – Castelvecchi
• Connections with other Chianti hiking routes via farm roads and local paths

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Who this route is suitable for

This itinerary is ideal for:

• moderately fit hikers,
• walkers interested in vineyard landscapes,
• slow and experiential tourism,
• routes linking historic villages and rural Chianti.