It is said the region south of Siena reflects the simple rural Tuscan life. This undulating landscape, deep green in spring and golden in fall, spreads out before you like a painter’s canvas, adorned with rows of cypress, quiet lanes and stone farmhouses. It is an expressive land, full of timeless pleasures and wonderfully preserved ancient habitations, many dating back to the Etruscan era more than two millennia ago.
There’s no better place to start an exploration here than Pienza, a gem of a Renaissance village commissioned by Pope Pius II to be rebuilt in the 15th century as an “ideal” city and papal residence. Set high above the wide and beautiful Val D’Orcia, with views of distant Monte Amiata, the highest peak in Tuscany, Pienza was the pope’s birthplace, known at that time as the rough-and-tumble village of Corsignano. (Pius II renamed it Pienza, in honor of himself.)
From the humble Piazza Dante, you enter the city walls following the main street, the Corso Rossellino, named after the town’s Florentine architect, Bernardo Rossellino. Pius II had dreamed of creating a model town with a single architectural scheme and in 1459 enlisted Rossellino to transform Corsignano into a city that exemplified Renaissance ideals. Pienza’s focal point is the Piazza Pio II, with its classically inspired Duomo and the Palazzo Piccolomini, considered Rossellino’s masterpiece. (As it turned out, during the building of Pienza, Rossellino embezzled the pope’s funds and spent three times his original budget. The pope, however, forgave the architect in gratitude for “these glorious structures which are praised by all except those consumed by envy.”)
Pienza is also renowned for its excellent local food products and exquisite ceramics. Visitors strolling the Corso are immediately struck by the strong wafts of pecorino cheese emanating from little shops, where one also finds fresh-made pastas, white truffles, flavor-infused olive oils and specialty meats, including the famous cinghiale (wild boar), pheasant, pork, and bistecca alla fiorentina—thick steaks grilled rare over charcoal and sprinkled with delicate spices.
I’ve been fortunate to stay in Pienza twice—the first time just off the Piazza Dante in a simple room above the Dal Falco restaurant (where I became addicted to the ethereal ravioli in truffle sauce). The second stay was a splurge: the luxurious Il Chiostro di Pienza, a onetime monastery now a Relais and Châteaux retreat just off the Piazza Pio II. Centrally located Pienza makes an ideal base for a three-day immersion in Tuscan culture, wine, cuisine, medieval art and architecture, coffee, and other Italian charms.
Monasteries and medieval hill towns
In my tiny rental car, I drove from Pienza down into the Val D’Orcia, following a cypress-lined road past a crumbling farmhouse, the Vino Nobile vineyards and sprawling fields of wheat, corn, barley and sunflower to the hill town community of Monticchiello. After a stroll through this walled village, with beautiful views of the valley and Pienza in the distance, I headed on the back roads to Montepulciano, the highest Tuscan hill town.
Built along a narrow tufa ridge, Montepulciano strikes a dramatic pose in the Tuscan hills. I ambled through the town’s winding streets, discovering hidden squares, Renaissance palaces and churches before pausing at an enoteca (wine cellar) just off the Piazza Grande. This was the perfect place to learn about and, of course, taste the region’s glorious reds, including Vino Nobile di Montepulciano and Brunello di Montalcino—the latter among the most heralded (and expensive) Tuscan wines.
After lunch of handmade pici pasta and fresh salad at a small trattoria, I descended steep steps from town to the Tempio di San Biagio, a pilgrimage church located just outside the town walls. Designed by Antonio da Sangallo the Elder to rival the churches of Assisi, Lourdes and Santiago de Compostela, San Biagio is one of Italy’s most significant examples of High Renaissance architecture.
From Montepulciano, I backtracked through Pienza to Montalcino, a classic Tuscan hill town. One of the primary architectural features here is La Rocca, a fortress that has been reconstructed from the ruins of 14th-century Sienese walls and now encloses a public park and an enoteca. I climbed the fortress’s Tower of San Martino for unforgettable views of Montalcino, the Val d’Orcia and distant Siena.
Just south of here is Sant’Antimo, home to a honey-toned Benedictine monastery—a brilliant example of Romanesque architecture, now maintained by French Cistercian monks, who celebrate mass in Gregorian chant several times a day. It’s not certain when the abbey was founded, but tradition attributes it to Charlemagne, who passed through the region with his army in 781.
Just north of Montalcino, in the sparsely populated Crete Senesi, where white clay hills form a surreal backdrop pressed against the sky, lies the Abbazia di Monte Oliveto Maggiore, arguably the best-known monastery in Tuscany. It was founded in 1313 by Sienese merchants whose desire to escape the ills and temptations of city life led to the creation of the Olivetan order. The loggia surrounding the monastery’s cloister contains a stunning series of 15th- and early 16th-century frescoes.
Southern Tuscany is also known for its ancient (and working) thermal spas. One such hot spot is Bagno Vignoni, a spa village that once catered to travelers making their way along the Via Francigena pilgrimage route. A Roman-era piscina (bath) is the main attraction in the town’s main square. Members of the Medici family—who built the site’s Renaissance arcade—and Saint Catherine of Siena were among those who soothed their tired limbs in this historic spot.
On the final leg of my Southern Tuscan odyssey, I drove across the Val di Chiana to Cortona, an enchanting hill town whose history dates back to Etruscan times. After the Etruscans came the Romans, who lived here until the settlement was destroyed by the Goths. In later years, the town fell under the patronage of Siena and Naples, and finally Florence. Today, rich in art and history, Cortona is a fascinating place to explore. Painter Luca Signorelli was born here in 1450; Florentine painter and Dominican friar Fra Angelico also made the town his home for ten years. The churches of Santa Margherita, San Domenico, Santa Maria del Calcinaio and San Niccolo are all worth a visit. With its array of trattorie and ristoranti, Cortona is also a wonderful place to enjoy lunch and soak in the refined atmosphere that defines Southern Tuscany.
