The Secrets of Tuscany’s Val d’Orcia

Ingrid K. Williams/Virtuoso

Anthony Lanneretonne

Here’s how to make the most of a visit to this remote, winery-filled Italian valley.

Every day, someone asks me where they should travel in Italy, from friends of friends planning a once-in-a-lifetime trip to repeat visitors looking for a new area to discover. As a longtime expat who’s spent 14 years exploring every corner of the country, I find myself whispering one destination’s name over and over: Val d’Orcia. A pastoral region south of Siena, this is the valley that, to me, epitomizes Tuscany: the gently rolling hills, the snaking country roads lined with slender cypress trees, silvery olive groves, abundant vineyards, and stone farmhouses. Nearly 20 years ago, this agricultural area was inscribed as a UNESCO World Heritage site, and today its rural roads and hilltop villages are clogged from early spring through late fall with cyclists, tour buses, and day-trippers eager to selfie-stick their way through Tuscany-land. But don’t let them deter you: Skirting the crowds is easy if you time it right, visit lesser-known villages, and seek out the many hidden gems strewn across this region spanning nearly 240 square miles. Here’s how I’d spend a few days reveling in all that makes the Val d’Orcia so special in the first place.

Montalcino.

Anthony Lanneretonne

High Point

Hopscotching between villages and detour-worthy sites is the best way to sample the Val d’Orcia’s offerings. One especially scenic place to start: the winding country road that passes acres upon acres of vineyards on the way to Montalcino, a medieval hill town best known for its brunello wine. Crowned by an imposing fourteenth-century fortezza, the village offers views from the fortress ramparts across the Orcia valley to the Sienese hills and Monte Amiata, a distant lava dome. In the historic center of this lauded wine-making town, you can’t throw a cork without hitting a wine bar or tasting room. One to seek out is La Sosta, an enoteca near the fortress with a wide selection of brunello and rosso di Montalcino from top producers.

When you return to the valley, stop at one of the area’s loveliest historical sites: the Abbazia di Sant’Antimo, a Romanesque abbey surrounded by wheat fields, vineyards, and olive trees. The abbey complex, which dates to the ninth century, now serves as a monastery for an order of nuns, who also run a small pharmacy with monastic tinctures, teas, preserves, and digestifs worth perusing after a visit to the austere travertine church.

Water Features

Since Etruscan times, weary travelers have sought the restorative hot springs of Bagno Vignoni. Located along the Via Francigena pilgrimage road, this village encircles an unusual main square: a large thermal pool ringed by a church and other handsome stone buildings. Although bathing is no longer permitted in the square, there are several places to take the waters in town. For pampered bathing, ease into the steaming pools at one of the town’s spas, such as Albergo Posta Marcucci, which features two large outdoor pools in a pretty garden. Or, for a more democratic experience, head down the hill to Terme Libere, an outdoor pool at the base of a trickling waterfall, where the mineral-rich water may not be piping hot, but access is free and the sociable atmosphere is distinctly Italian.

A peekaboo view of Pienza.

Anthony Lanneretonne

Lunch Break

On a walk around the peaceful walled hamlet of San Quirico d’Orcia, one of the region’s lesser-known villages, take a turn in the Horti Leonini, classical Italian-style gardens designed in the 1500s with symmetrical hedges, trees, and greenery dotted with sculptures. Just outside the town walls, I always join the locals gathered at La Bottega di Portanuova, an organic deli, bar, and café, for platters of salumi and cheeses from small area producers. The friendly young proprietors, Roberta Vegni and Luigi Mariotti, serve a selection of natural wines (a rarity in Tuscany) and local craft beers. On your way out of town, take it slow on the drive toward Pienza – you won’t want to blow past the rolling meadows and miss the tiny, jewel-box Vitaleta Chapel, flanked by cypress trees atop a nearby hill. Every time I drive by, I’m compelled to pull over to take yet another photo of this adorable chapel.

Dinner at Idyllium in Pienza.

Anthony Lanneretonne

Evening Out

Pienza takes the crown as the most photogenic village in a valley filled with beauties. And a showstopper was precisely what Pope Pius II intended in the fifteenth century when he decided to transform his rural hometown into the ideal Renaissance village. His papal summer palace, Palazzo Piccolomini, anchors the main square and is open for tours of its harmonious architecture, charming garden, and elegant porticos.

Arrive at sunset, when the day-trippers have departed and the narrow, stone-paved lanes glow in Pienza’s historic center, which is dotted with cozy ristoranti, trattorie, and osterie. The hands-down homiest, however, is Sette di Vino, a friendly osteria where owner Luciano Monachini plops straw-wrapped carafes of red wine on the table and suggests simple, rustic dishes to share, such as garlicky white-bean soup and grilled pecorino topped with crisp strips of rigatino toscano, a local pancetta. After dinner, the spot for a nightcap is Idyllium, a restaurant and cocktail bar located in the former stables beneath Palazzo Piccolomini. Run by bartenders who learned the trade at Milan’s top bars, this stylish hideaway serves inventive cocktails to a convivial crowd that skews young and local.

La Foce’s Dopolavoro restaurant, built in 1939.

Anthony Lanneretonne

Into the Countryside

Prepare for a bumpy drive along the rural dirt road to Podere Il Casale, an organic farm and dairy located on a hilltop outside Pienza. Ulisse Brändli, a Swiss expat who bought this land more than 30 years ago with his partner Sandra Schmidig, leads tours of the farm while explaining the cheese-making process and extolling the virtues of biodynamic, full-circle farming. Tours conclude on the pergola-covered terrace with a tasting of the dairy’s raw-milk pecorino and caprino cheeses, accompanied by the farm’s own honey, fruit preserves, olive oil, breads, and sangiovese.

Tucked on a hillside on the valley’s eastern edge, the fifteenth-century La Foce estate might be the area’s best-kept secret (despite being featured on the hit HBO series Succession). Spend an hour strolling its vast landscaped garden, past wisteria-covered walkways, blooming roses, potted lemon trees, and fragrant lavender hedges. Best of all is the property’s spectacular view across the tapestry of the Val d’Orcia’s quintessentially Tuscan countryside.

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