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Walking in Southern Tuscany - Art, architecture & landscapes in the Val d’Orcia & Chianti

Five walks of between 4 and 10 kilometres through exquisite landscape of soaring cypress, olives and vines.

Art history away from the tourist throngs – medieval fortress towns, Romanesque churches, Renaissance palazzi, Sienese painting. 

Based in two tiny towns in topographically diverse areas of Tuscany.

Two wine tastings, in Montalcino and Badia a Coltibuono.

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14 - 21 Oct 2024 Fully booked

  • Pienza, Capitelli Cortile (detail).
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To walk through quintessentially Tuscan landscapes, along chalky tracks lined with soaring cypress trees and flanked by neat rows of vines and well-kept olive trees, must surely be one of life’s great pleasures. The walks selected here pass through farmland and woodland, where primrose, violet and cyclamen nestle below chestnut, holm oak and beech. Pine trees grace the higher terrain. Walking is conducive to observing at close quarters the variations of plant, animal and birdlife in this enchanting countryside.

But if seeing the artistic and architectural delights in these parts of Tuscany is your aim, this tour also offers opportunity to do so. We avoid the tourist throngs in the larger towns and cities and concentrate on the smaller and less-visited places. Medieval fortress towns, Romanesque churches, Renaissance palazzi and paintings of the Sienese school are particularly in evidence here. Sometimes these are seen at the beginning or the end of a morning’s walk, sometimes during a half day spent in leisurely exploration of one of the enchanting little cities or settlements. All are seen in the enlightening company of an art historian.

And while the walks are taxing enough to ensure that hearty evening meals are fully deserved, they are not so strenuous as to detract from enjoying the ever-changing views and natural, agricultural and constructed sights.

We take trouble to ensure that much of what you eat is produced from fine local ingredients, including Pecorino cheese (whose pungent flavour is due to the herbs grazed by ewes on the unique clay soils south of Siena) and the prized salami of the cinta senese pigs. The food is often perfectly complemented by a glass of one of the world’s finest red wines.

As this tour is based for three nights in Radda in Chianti, today still the nucleus of Tuscan viticulture and where the noble Sangiovese vine is most prevalent, opportunity is allowed for tastings of these robust reds. We also visit a producer of some of the finest Chianti Classico, in a former monastery where thirsty monks made a wine similar to the sophisticated Chianti produced today.

Day 1

Fly at c. 8.45am from London Heathrow to Pisa (British Airways). Drive to Pienza, a  gem of Renaissance architecture created by Pope Pius II as a tribute to his place of birth, which is the base for four nights.

Day 2

San Quirico, Pienza. Drive to the little walled town of San Quirico d’Orcia. Visit the Collegiata with its splendid portals and the Horti Leonini, public gardens dating to the 17th century. A moderate walk back to Pienza through rolling, open farmland of rare beauty, visiting the Romanesque church of Corsignano before the steady climb to Pienza: c. 6 km, 2½ hours. In the afternoon, explore this little city where at the centre the cathedral, episcopal palace and Pius’s own palazzo form a harmonious group.

Day 3

Monticchiello, Montepulciano. The medieval hamlet of Monticchiello, with views across Val d’Orcia, is the starting point for a moderate morning walk through a valley, before continuing uphill to Pienza: c. 6 km, 2½ hours. Montepulciano is one of the most picturesque of Tuscan hill towns, with grey stone palaces piled up towards the main square at the apex. The cathedral here is rich in Renaissance works of art, while outside the walls is a centrally planned church, a Renaissance masterpiece.   

Day 4

Sant’Antimo, Montalcino. An easy walk from near Montalcino, downhill through a pretty valley, part vineyard, partially wooded, punctuated by farmsteads, and arrive at the remote and serene monastery of Sant’Antimo: c. 7 km, 2 hours. This most beautiful of Romanesque churches is in part constructed of luminous alabaster. Once an impregnable fortress and now centre of Brunello wines, Montalcino is a hilltop community with magnificent views and a collection of Sienese paintings in the civic museum. There is a wine tasting here. Return by coach to Pienza.

Day 5

Monte Oliveto Maggiore, Asciano. The monastery of Monte Oliveto Maggiore is a fine complex of Early Renaissance art and architecture, the cloister having 36 frescoes by Signorelli (1445–1523) and Sodoma (1477–1549). Break the journey in Asciano, a delightful town sitting in the heart of the Crete Senesi, a name referring to the clay crags typical of this area. Radda in Chianti, once the capital of the Chianti League established in 1250, is one of the most attractive of the region’s settlements. Stay three nights in Radda.

Day 6

Gaiole in Chianti, Badia a Coltibuono. From Gaiole, walk a pleasantly varied, challenging route through Chianti countryside with woodland, vineyards and breath-taking vistas: c. 10 km, 3½ hours. Badia a Coltibuono, a former abbey founded by Vallombrosan monks, has an important history of viticulture. Lunch and wine tasting at the estate restaurant before a visit to the abbey’s 16th-century frescoed refectory, gardens and wine cellars. 

Day 7

Badiaccia Montemuro, Volpaia. An optional, moderate morning walk through variegated woods including oak and silver birch to the well-preserved hamlet of Volpaia: c. 6 km, 2½ hours. The village is dedicated to the arts and wine-making, ensuring its original architectural features remain intact. A further moderate, optional walk in the afternoon descends through the estate’s impressively maintained vineyards to the valley floor before climbing to Radda: c. 4.5 km, 2 hours.

Day 8

Fly from Pisa, arriving London Heathrow at c. 2.00pm.

Image of Thomas-Leo True

Dr Thomas-Leo True

Art historian specialising in Renaissance and Baroque architecture in Rome and the Papal States, and Assistant Director of the British School at Rome from September 2015. He received his doctorate from Cambridge University, and also studied at the British School at Rome, where he was Rome Scholar (2009–10) and Giles Worsley Fellow (2013). He has lived in Le Marche region of Italy and is currently writing his first book on the Marchigian Cardinals of Pope Sixtus V.

Price, per person

Two sharing: £2,910 or £2,750 without flights. Single occupancy: £3,220 or £3,060 without flights.


Flights (Euro Traveller) with British Airways (Airbus 320); travel by private coach; hotel accommodation as described below; breakfasts; 3 lunches (two including wine tastings) and 4 dinners with wine, water, coffee; all admissions; all tips for restaurant staff and drivers; all taxes; the services of the lecturer and tour manager.


Relais Il Chiostro, Pienza: 4-star former friary dating to the 15th century close to the main square; bedrooms vary in size and are simply decorated and furnished; the gardens and terrace have an impressive view and the restaurant serves good Tuscan cooking. Relais Vignale, Radda in Chianti: 4-star 17th-century manor house with historical links to Chianti wine production; several lounges, terrace with valley view, restaurant and outdoor pool; rooms vary in size. Single rooms are double rooms for sole use throughout.

How strenuous?

This is a walking tour, graded moderate. There are 6 walks: 1 is easy, 3 are moderate (of which 2 are optional) and 1 is challenging. It is essential for participants to have appropriate walking footwear, be in good physical condition and to be used to country walking with uphill and downhill content. If you are used to them you may find walking poles useful. Average distance by coach per day: 44 miles.

Are you fit enough to join the tour?

Group size

Between 10 and 18 participants.

Travel advice

Before booking, please refer to the FCDO website to ensure you are happy with the travel advice for the destination(s) you are visiting.

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Bulgaria, 28 September–7 October 2024

'Excellent – met our expectations to a very high degree.'

'Very good balance of visits.'

'An outstanding lecturer: enthusiastic.'