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Val D’Orcia and the Sienese Hills - lesser-known delights of Southern Tuscany

Hilltop towns and villages, spectacular countryside.

Based throughout in the charming Renaissance town of Pienza.

A good mix of architecture and art with a day spent in Siena.

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10 - 16 Apr 2025 £2,610 Book this tour

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This tour is representative of a category in which there is a shift of emphasis away from the major masterpieces of a region towards the lesser delights, from a concentrated diet of cultural achievement familiar from text books towards a mélange of landscape, less accessible art and a sense of the continuity of life and community amidst ancient masonry.

All six nights of the tour are based in the small hill town of Pienza. Formerly called Corsignano, it was the birthplace of Pope Pius II, humanist, historian, traveller, autobiographer and patron of architecture. Between his election in 1458 and his death in 1464 he commenced the rebuilding of his home town and provided it with a cathedral, bishop’s palace, town hall, a palace for himself and a new name. Consequently Pienza entered the annals of architectural history as the earliest example of Renaissance town planning.

If you delight in places which lie off the beaten track, in tiny hill towns where vineyards clamber up to the 14th-century walls, in majestic landscapes of storm-tossed hills punctuated by cypresses, in the discovery of great architecture and exquisite paintings in unexpected places, in tracing a maze of alleys scarcely changed for 500 years, this tour is likely to please.

Day 1

Pienza. Fly at c. 8.30am from London Heathrow to Pisa (British Airways). From there drive to Pienza, a gem of Renaissance architecture set in some of the best of Tuscan landscape. Late-afternoon visit to the Palazzo Piccolomini, built as a summer residence for the pope and now containing a small museum.

Day 2

Castelnuovo dell’Abate, Montalcino, Pienza. Located in a remote valley, the partly ruined monastery of Sant’Antimo has a strikingly beautiful Romanesque church, in part constructed of luminous alabaster. Once an impregnable fortress and now centre of Brunello wines, Montalcino is a walled hilltop village with magnificent views and a collection of Sienese painting in the museum. In the afternoon, continue the leisurely exploration of Pienza, the tiny hill town rebuilt 1459–64 by Pope Pius II in accordance with Renaissance ideals. The cathedral and palaces grouped around the main piazza were designed by Bernardo Rossellino in collaboration with his papal patron. Visit the cathedral and the diocesan museum in the restored Palazzo Borgia.

Day 3

Montepulciano, La Foce. The main thoroughfare of Montepulciano, lined with grand palaces, winds circuitously through this once important city, with the Piazza Grande at the summit. The cathedral here is rich in Renaissance works of art. Outside the town, the centrally planned church of San Biagio by Antonio da Sangallo is one of the masterpieces of the Renaissance. Villa La Foce, former home of Iris Origo, has a garden designed by Cecil Pinsent.

Day 4

Montesiepi, San Galgano, San Gimignano. In the parish churches of San Leonardo al Lago and Montesiepi are two remarkable Sienese paintings of the Annunciation, respectively by Lippo Vanni and Ambrogio Lorenzetti. At San Galgano are the impressive Gothic ruins of what in the 13th century had been one of the richest Cistercian abbeys in Italy. In San Gimignano the group visits a town hall with 14th-century frescoes and a small art gallery, as well as a Romanesque Collegiata which contains two cycles of trecento frescoes.

Day 5

Siena. Siena, City of the Virgin, is the most beautiful of Italian hill towns. Palazzo Piccolomini (1460s) contains the archives and a museum displaying beautifully painted covers of civic records. Visit the hospital of Sta. Maria della Scala, with its exceptional collection of Renaissance frescoes. The imposing cathedral, a Romanesque and Gothic construction of white and green marble, offers an outstanding array of sculpture and painting. Especially deserving of close attention are the crypt and Pinturicchio’s frescoes in the Piccolomini Library.

Day 6

Monte Oliveto Maggiore, Bagno Vignoni. In the morning visit the monastery of Monte Oliveto Maggiore, an exquisite complex of Early Renaissance art and architecture, the main cloister having 36 frescoes by Signorelli and Sodoma (1505–8). Bagni Vignoni has a central square occupied by an arcaded Renaissance piscina. Return to Pienza for a free afternoon.

Day 7

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

Image of Fabrizio Nevola

Professor Fabrizio Nevola

Chair and Professor of Art History and Visual Culture at the University of Exeter, specialising in urban and architectural history of Early Modern Italy. He obtained his PhD at the Courtauld Institute and has held fellowships at the University of Warwick, the Medici Archive Project, and Harvard University’s Villa I Tatti (Florence). He has published widely including the award-winning Siena: Constructing the Renaissance City.

Price, per person

Two sharing: £2,610 or £2,440 without flights. Single occupancy: £2,880 or £2,710 without flights.


Flights (Euro Traveller) with British Airways (Airbus 320); travel by private coach; hotel accommodation as described below; breakfasts; 2 lunches and 3 dinners with wine, water and 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. Single rooms are doubles for sole use throughout.

How strenuous?

The tour involves a lot of walking in town centres, where coach access is restricted, and a lot of standing in museums and churches. A good level of fitness is essential. You will be on your feet for lengthy stretches of time. Average distance by coach per day: 76 miles.

Are you fit enough to join the tour?

Group size

Between 10 and 22 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.

Combine with

In 2025:

Minoan Crete28 March–5 April

Normans in the South, 1–9 April

Art in Madrid, 2-6 April

Romans & Carolingians, 2–9 April

Cornish Houses and Gardens, 22–30 April

The Cathedrals of England, 23 April–1 May

'A fantastic programme of art.'

'Each day had a variety of venues.'

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