5 Tuscan Villages to Visit at Least Once in a Lifetime

Hills covered with vineyards, ancient walls, stone-paved streets and landscapes that look as though they have been painted: Tuscany’s historic villages preserve the region’s most authentic soul. Here are five destinations to visit at least once in a lifetime.

San Gimignano, the Town of Towers

With its unmistakable medieval skyline, San Gimignano is one of the best-known towns in Tuscany. Of the many towers built by the most powerful families during the Middle Ages, fourteen remain today.

The heart of the town is formed by Piazza della Cisterna and Piazza del Duomo. From the top of Torre Grossa, visitors can enjoy a magnificent view over the Val d’Elsa.

Before leaving, it is worth tasting Vernaccia di San Gimignano wine and the locally grown saffron.

The historic centre has been recognised as a UNESCO World Heritage Site since 1990.

Pienza, the Jewel of the Val d’Orcia

Pienza is a small Renaissance town surrounded by the spectacular landscape of the Val d’Orcia.

In the fifteenth century, Pope Pius II decided to transform his birthplace into an “ideal city”, entrusting the project to the architect Bernardo Rossellino.

A visit can begin in Piazza Pio II, overlooked by the Cathedral, Palazzo Piccolomini and the Town Hall. Do not miss a scenic walk along the town walls and a tasting of the famous Pecorino di Pienza cheese.

Pitigliano, the Town of Tuff

Perched on a tuff cliff in the heart of the Maremma, Pitigliano appears to rise directly out of the rock. The town is a fascinating maze of narrow streets, arches, stairways and ancient houses.

It is also known as “Little Jerusalem” because of its historic Jewish community. In the Jewish quarter, visitors can explore the synagogue, the unleavened bread bakery and rooms carved into the tuff.

Nearby are the Vie Cave, ancient Etruscan pathways cut deep into the rock. They offer a particularly atmospheric experience for those who enjoy walking in nature.

Montepulciano, Among Palaces and Vineyards

Montepulciano overlooks the Val di Chiana from the top of a hill.

Its historic centre, which has medieval origins but a predominantly Renaissance appearance, is filled with elegant palaces, churches and underground wine cellars.

Following the main street uphill leads to Piazza Grande, the monumental heart of the town. Just outside the centre stands the Temple of San Biagio, one of the finest examples of Tuscan Renaissance architecture.

Montepulciano is also closely associated with Vino Nobile, which can be tasted in the town’s historic wine cellars.

Volterra, Following in the Footsteps of the Etruscans

Volterra brings together Etruscan, Roman and medieval heritage.

Its most important attractions include Porta all’Arco, the Guarnacci Etruscan Museum, the Roman Theatre and Piazza dei Priori.

The town is also known for alabaster craftsmanship, a tradition that remains alive in the workshops of the historic centre.

Walking along the ancient walls, visitors will find numerous panoramic viewpoints overlooking the surrounding countryside.