Famously picturesque Tuscan towns such as Volterra and San Gimignano are often overrun in high season. On this trip, we visited Montalcino and Pienza, places that tend not to be quite so crowded.
Perched on a hill, with prominent fortifications and winding streets, Montalcino is the embodiment of a medieval town. It is filled with restaurants and shops, many of which provide opportunities to sample the celebrated wine of the region: Brunello di Montalcino. A fine place to stop for a bite and a glass of Brunello is Enoteca Osteria Osticcio (Via Matteotti 23, Tel. [39] 0577-848271). Tullio and Francesca Scrivani have created a wonderful space, with glorious views of the surrounding countryside. Although the Scrivanis sell wine, the largest selection from local producers is to be found within the town’s 14th-century fortress, at Enoteca la Fortezza di Montalcino. The staff are knowledgeable, and the shipping back home is reasonable.
A seven-mile drive east of Montalcino, Pienza has a completely different character. Native son Pope Pius II yearned to transform his hometown into an ideal of Renaissance aesthetics. To that end, he commissioned Bernardo Rossellino, a student of the great Leon Battista Alberti, to create a papal palace, town hall and cathedral. Today, the town is a charming and beautiful place, laid out in a easy-to-comprehend plan. For a light meal and a glass of wine in a pleasant setting, try Osteria Sette di Vino (Piazza di Spagna 1, Tel. [39] 0578-749092), where you will find a special menu that features the fine local Pecorino cheese.
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