The region south of Siena, the crete Senesi, represents a quieter, simpler side of rural Tuscan life. This undulating landscape of gorgeous hills, deep green in spring and golden in fall, spreads out before you like a great painter’s canvas, punctuated by rows of cypress, quiet lanes and stone farmhouses. It's an expressive land, full of timeless pleasures and wonderfully preserved ancient habitations, many dating back to the Etruscan era more than two thousand years ago.
There’s no better place to start an exploration here than the village of Pienza, a Renaissance gem commissioned by Pope Pius II 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, highest peak in Tuscany, Pienza was the birthplace of this pope, and was known at the time as the rough-and-tumble village of Corsignano (he later renamed it Pienza, in honor of himself.)
From the modest 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 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 fresh 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 that are typically 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 their ethereal ravioli in truffle sauce.) The second stay was a splurge: the Relais Il Chiostro di Pienza, a one-time monastery now a luxurious retreat just off the Piazza Pio II.
For me, centrally-located Pienza was an ideal base for a three-day exploration of Southern Tuscany. For total immersion in Tuscan culture, wine, cuisine, medieval art and architecture, coffee, and other Italian charms, this was the place to be.
Monasteries and medieval hilltowns
In my tiny rental car, I drove from Pienza down into the Val D’Orcia, following a cypress-lined roads past crumbling farmhouse, passing Vino Nobile vineyards and sprawling fields of wheat, corn, barley and sunflower to the hill town community of Monticchiello, a walled village with beautiful views of the valley and Pienza in the distance. After a stroll through town, I headed on the backroads 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 in-house enoteca. I climbed the fortress’ tower of San Martino for unforgettable views of Montalcino, the Val d’Orcia and distant Siena.
Just south of here is the famous monastery of Sant’Antimo. This honey-toned Benedictine monastery—a brilliant example of Romanesque architecture—is maintained today 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 press against the sky and create a surreal backdrop, lies the Abbazia di Monte Oliveto Maggiore, arguably the best-known monastery in all of Tuscany. It was founded in 1313 by a group of Sienese merchants whose desire to escape the ills and temptations of city life led to the creation of an order known as the Olivetans. 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 still working) thermal spas. One such hot spot is Bagno Vignoni, an ancient geothermal spa village that originally 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 tired limbs in this unique and historic spot.
On my final leg of my Southern Tuscan odyssey, I drove across the Val di Chiana to Cortona, an enchanting hill town whose long 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 lay under the patronage of Siena and Naples, and finally Florence. Today, rich in art and history, the Cortona is a fascinating place to explore. Painter Luca Signorelli,was born in here in 1450 and Florentine painter and Dominican friar Fra’ Angelico alsomade Cortona his home for 10 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.
Tuscany Travel Tips
Southern Tuscany is best toured by car (rentals are available in nearby Siena or Florence), bicycling or walking tour. For energetic travelers, Berkeley-based Backroads offers cycling and walking tours in the region. Their six-day, five-night bicycle tours (from $4398, luxury inns and $3298, casual inns) are a wonderful way to get a fresh air view of this special region of Italy.