Extending from the hills just south of Siena to Monte Amiata, the Val d’Orcia or Valdorcia lays claim to an important stretch of the Francigena.

Have you seen those postcard-perfect images of Tuscany with hills like lapping waves topped by a perfectly S-curving road lined with Cyprus trees? Where each hill is topped with a canary yellow villa with a terracotta-tilled roof? Those idyllic photos that seem to say, “This is paradise. You need to retire here.” . . .

That’s the Val d’Orcia.

Val d'Orcia History

Inscribed into the UNESCO World Heritage List for its idealized agrarian and pastoral landscape, the Val d’Orcia has been memorialized in paintings, novels, and poems since the lauded Renaissance Sienese school.

Its too-good-to-be-natural landscape was actually planned by the Sienese merchant class, who landscaped the hillside in the 14^th and 15^th centuries after Lorenzetti’s ideal landscape fresco painted in Siena’s town hall between 1338 and 1340.

Via Cassia/Francigena in the Val d'Orcia

Extending from the hills just south of Siena to Monte Amiata, the Val d’Orcia or Valdorcia lays claim to an important stretch of the Francigena, the late Medieval and Renaissance pilgrim path between France and Rome that was known in the Roman era as the Via Cassia.

While the original Via Cassia stuck to flatter ground, as most arrow-straight Roman roads did, invasions and attacks from Byantines and other northern tribes in the end of the first millennium AD forced the main road to move into the hillside and become the Francigena, which takes in towns like Siena and Pienza that were not part of the original Roman road system.

What to See in the Val d'Orcia

Siena

Until Florence defeated Siena during the Renaissance, it was the major trading, banking, and agrarian powerhouse of Tuscany. The riches from that period supported the building of marvelous architecture, like the Piazza del Campo pictured above.

Day trip: San Gimignano, a UNESCO World Heritage Site that preserves the typical medieval city skyline with its 14 extant towers.

Stay: Siena Grand Hotel Continental (expensive)

Pienza

The birthplace of Pope Pius II or Enea Silvio Piccolomini, Pienza was rebuilt under the Pope's direction into an ideal, harmoniously-proportioned and aesthetically-appointed city according to humanist urban planning principles.

Day trip: Castiglione della Pescaia, an ancient seaside town now home to a winery Alain Ducasse collaborates on.

Stay: Hotel Piccolo le Valle (budget)

Montepulciano

A hilltop town know for its Vino Nobile wine and the excellent meat, cheese, and pasta from the farms at the base of the town.

Day trip: Montacino, home of the world-famous Brunello di Montalcino wine, and Sant’Antimo, an abbey marking the spot where Charlemagne cured his army from the plague.

Stay: Agriturismo Dionora (mid-range)

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