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

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.

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.

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.

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.

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.

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