Classic Chianti Pathways ~ 7 days in the Chianti Classico

Radda township & welcome dinner provided
2 hours exploring Radda’s history

We arrive in Radda in time explore this historic town and appreciate life in Chianti over the centuries.

In the evening our host will introduce us to a selection of local foods and wines, sharing with us their extensive knowledge.

Poggio San Palo Ring Walk
4.5-5.0 hours easy
Picnic lunch provided

This walk is very special as it provides an opportunity to enjoy the traditional Tuscan landscape and glimpse of rural life as it has been for the past millennium. With the revitalisation of Chianti’s wine industry, larger holdings of vineyards are rapidly replacing the traditional terracing and intermingling of various crops.

At times we see examples of olives trees planted in the same row with widely spaced vines along centuries old terraces. At the end of the row is the occasional fig tree, rather than 5 today’s concentration on just hectares of tightly planted vines.

As we leave Radda old terraces are in abundance, often with the family vegetable garden at one end complete with a collection of bamboo poles strategically placed for tomato trellising. The track then descends through a cool valley with numerous streams joining the main river. The shaded pathways along the way are bound by historic stone fences, many still in excellent condition. At lunchtime we stop for a picnic in the very pretty, yet tiny town of Poggio San Palo.

Radda, Volpaia Ring walk
4 hours easy to moderate
Picnic lunch provided
Dinner provided

From the walls of Radda we can view the beautiful fortified hill town of Volpaia. It seems just a stone’s throw away.

Our journey to Volpaia will take us through olive groves, well tendered vineyards, woodlands and streams. In spring, the verges are abundant with wild flowers and herbs. In autumn, the colours mellow and the smell of ripening grapes is in the air. Interspersed along the way will be restored stone houses, historic churches, tabernacles and the Agriturismo village of Castelvecchi. We will see firsthand everyday Tuscan rural life with its constant farming activity.

Castello di Volpaia our mid point for the walk stands in a splendid panoramic position (617m). Wine and olive oil has been produced here since the 11th century. Today, the wine and oil production is housed throughout the village buildings, including a deconsecrated church. We will be met by a guide to take us on a most unique tour including a wine, olive oil and cheese tasting. Following the tour we circle back to Radda via the Romanesque Church of Santa Maria Novella.

Castellina to Radda
3.5 hours easy to moderate

A pleasant walk between two of the three Chianti League hill towns. Our walk begins by local bus taking us to the small pleasant medieval town of Castellina. This hill town holds its place in history as being on the front line of the wars which continually took place between Florence and Sienna.

Before beginning our walk we will explore remaining fortifications built during this period and take a short side trip to visit the Montecalvario Etruscian Tombs dating back to the 4th century BC. These are formed in a unique artificial hill and contain four sizeable underground burial chambers.

On leaving the outskirts of Castellina, our path takes us up an easy climb through oak woods. The track then broadens out into open terrain, with some of the best expansive views in this area.

We then make our way down through a pretty valley before returning to Radda.

The Lamole to Radda walk via Villa San Michelle, Badia a Montemuro and Volpaia
5.5 hours moderate
Picnic lunch provided

Our day starts with an early morning local bus to Greve. We then catch a piccolo bus that winds up to 600 metres giving panoramic views of the Chianti Classico wine growing region.

Our walk starts in Lamole from a small piazza with its 14th century Romanesque church. The walk winds steadily past stone walls and small village gardens. The mountains of the Apennines can often be seen in the distance.

We will have several breaks along this walk at San Michelle and Badia a Montemuro, an absolute gem. Lunch will be in Volpaia’s small yet stunning piazza.

Gaiole Ring walk
4 hours undulating with some short, steep climbs
Farewell dinner provided

From the walls of Radda you will have noticed Vistarenni standing grandly on the horizon. Our walk winds through olives groves and shaded woods past this 16C baroque villa. As we ascend we are rewarded with panoramic views and catch glimpses of the pretty 10C fortified hamlet Vertine. A steep descent takes us into Gaiole situated in the valley. Gaiole was an important market town due to its position on the cross roads between the Chianti district and the upper Arno valley. The river Massellone runs through the town. Gaiole is also one of the three towns forming the Chianti League, along with Radda and Castellina. A steady climb and we are rewarded with time to explore Vertine before returning to Radda.

Bus to Florence and to points beyond