Sant’Antimo, Montalcino. Once an impregnable fortress and now centre of Brunello wines, Montalcino is a hilltop community with magnificent views and a collection of Sienese painting in the museum. There is a wine tasting here. Walk down from Montalcino through the pretty Brunello valley, part vineyard, partially wooded, punctuated by farmsteads, and arrive at the remote and serene monastery of Sant’Antimo (c. 5.5 miles). This most beautiful of Romanesque churches is in part constructed of luminous alabaster. Return by coach to Pienza.  

Montepulciano, Monticchiello. 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. The mediaeval hamlet of Monticchiello, with views across Val d’Orcia, is the starting point for a late afternoon walk through a valley leading to Pienza (c. 4 miles). Overnight Pienza.  

Monte Oliveto Maggiore, Asciano, Radda. The monastery of Monte Oliveto Maggiore is a fine complex of Early Renaissance art and architecture, the cloister having 36 frescoes by Signorelli and Sodoma (1505–8). Asciano sits in the heart of the Crete senesi (a name deriving from the chalky earth), and has a museum containing 14th and 15th-century Sienese paintings. Radda in Chianti, once the capital of the Chianti League established in 1250, is one of the most attractive of the region’s settlements. First of three nights in Radda.  

From Gaiole, walk a pleasantly varied route through Chianti countryside with woodland, vineyards and breath-taking vistas (c. 6 miles). 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.

Castello di Volpaia. The well-preserved hamlet of Volpaia hides sophisticated wine cellars within its mediaeval walls. The village is dedicated to the arts and wine-making, ensuring its original architectural features remain intact. Walk down through the estate’s impressively maintained vineyards to the valley floor before a climb to Radda (c. 5 miles).

Fly from Pisa, arriving London Heathrow at c. 2.30pm.