Classic Chianti Pathways

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Situated in the beautiful hilly region between Florence and Siena is Radda in Chianti, a small unspoilt hill town which retains many original medieval features.  The town provides an excellent base for exploring the most typical and beautiful parts of Chianti.  Picturesque medieval hamlets, shaded woodlands, vineyards, olive groves, villages and stone farmhouses make walking through this area a real treat.

Radda in Chianti was the capital of the Chianti League in the 13th century and is now the capital of the Chianti Classico wine country. Wine lovers will be delighted with the town’s many Enotecas (wine bars) ideal places to sample the wide selection of wines this district has to offer. Others will find joy & magic in the slow-paced simplicity of everyday town life.

Our accommodation in Radda is a delightful family run hotel in the centre of the town complete with views of both the Chianti countryside and the character-filled streets. It is a charming building with traditional wood beam ceilings fully restored with all of today’s modern facilities. Plus, we can guarantee a warm and generous welcome that immediately makes you feel at home.

Day 1

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.


Tonight we will savour the simple delights of Tuscan food. Our host Monica will introduce us to a selection of local foods and wines, sharing with us her extensive knowledge.


Day 2

Poggio San Palo Ring Walk
4.5-5.0 hours easy to moderate
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 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.

Day 3

Radda, Volpaia Ring Walk
4 hours easy to moderate. Including a 1hr. tour of Volpaia winery & olive oil factory.
Picnic lunch provided
Dinner provided


From the walls of Radda we can view the beautiful fortified hill town of Volpaia. 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 first hand 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. A guide will lead us on a most unique tour concluding with a wine, oil and cheese tasting. Following the tour we circle back to Radda via the Romanesque Church of Santa Maria Novella.

Day 4

Castellina to Radda Walk
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 Etruscan Tombs dating back to the 4th century BC. We will also visit the Etruscan Museum and Tower. Contemporary Italian design blended with the original eleventh century castle plus the panoramic views make this a very worthwhile visit.

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.

Day 5

Lamole to Radda Walk via Villa San Michelle, Badia a Montemuro and Volpaia
5.5 hours moderate
Picnic lunch provided
Dinner “An Evening in a Tuscan Kitchen”


An early morning ride on a 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.

Day 6

Gaiole Ring Walk
4-4.5 hours easy to moderate, undulating with some short, steep climbs.


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.

Day 7

Bus to Florence and to points beyond

Our three dinners include ...

  • Experiencing a taste of Chianti with a wine tasting followed by traditional Tuscan fare made with local produce. Our delightful host shares her extensive knowledge of wine and food with us.
  • A dinner on the edge of a walled medieval town watching the misty Tuscan sun slide down behind the Chianti hills.  Relax the tired legs and feel the satisfaction that you have walked the quiet, hidden pathways that spread out below you.
  • Learning to cook Tuscan style in a traditional stone farmhouse. Using recipes, techniques and stories, we prepare our dinner with fresh produce available on the day. We then share the fruits of our labour over fine Chianti wine allowing time to discover local Tuscan life from our host’s perspective.

Tour dates:

May 7th – 13th 2010

September 3rd – 9th 2010

October 1st – 7th 2010

Tour Price:

$2,600 twin share
Includes all breakfasts, 3 lunches, 3 dinners, two guides and all transportation from Florence, local transport, entrance & wine tour fees.
Not included are wines and other beverages with alcohol.
Note: A supplement of $500 applies for a single room
Special Offer: If you book two walks back to back a 10% discount applies