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Pieve a Castello

'A Special Place'

About Pieve a Castello

Tucked into the wooded hills between Siena and Florence, Pieve a Castello is one of the oldest and most perfectly preserved early medieval buildings in Europe. This extraordinary complex - a Romanesque canonry with origins dating back to the 8th century - has been lovingly restored as an exclusive place of retreat, reflection, and cultural exploration.

Surrounded by vineyards, olive groves, and the quiet echoes of the Via Francigena, Pieve a Castello is not only a place to stay - it is a place to connect: with history, with landscape, with art, and with the enduring spirit of Tuscany. From the warmth of its solar-assisted underfloor heating to the gentle toll of its ancient bell, everything about this site speaks of timeless continuity and thoughtful renewal.

Vineyards surrounding Pieve a Castello in the Tuscan countryside

A Walk Through Time:
Pieve a Castello's History

To truly appreciate the character of Pieve a Castello, one must step back through the centuries. What follows is a brief historical timeline, tracing the remarkable story of this site - from its early spiritual roots to its present-day role as a haven for learning and cultural enrichment.

Pieve a Castello swimming pool
Kate and Christopher Whinney
Aerial view of Pieve a Castello’s central courtyard and Romanesque buildings
Peaceful garden view through cloister arch at Pieve a Castello
Rolling hills of the Val d’Orcia near Pieve a Castello, Tuscany
Vineyards surrounding Pieve a Castello in the Tuscan countryside
Pieve a Castello organic kitchen garden
Historic painting representing the Black Death’s impact on Tuscany
Fresco detail by Lorenzetti symbolising prosperity during Pieve a Castello’s medieval peak
Ancient path of the Via Francigena near Pieve a Castello, used by pilgrims for centuries
Panoramic image of Pieve a Castello in morning light, highlighting its Romanesque structure
Fresco detail by Lorenzetti symbolising prosperity during Pieve a Castello’s medieval peak
Stone church and monastery buildings surrounding the courtyard at Pieve a Castello
Interior detail of stonework and early medieval design at Pieve a Castello
Distant view of Pieve a Castello framed by Tuscan fields and woodland

500 BC

Etruscan Foundations

An early Etruscan settlement, with a temple of imported granite, marks the beginning of habitation on the site. Alabaster artifacts confirm its ancient importance.

260 BC

Roman Arrival

Rome annexes Volterra. 'A Castello' becomes a Roman castrum, built around a courtyard; an Etruscan hearth stone still lies there today.

568-9 AD

Longobards Transform Italy

The Longobards cross into Italy and reshape the landscape. 'A Castello' evolves under their influence, gaining strength and religious significance.

5th-6th C AD

Turmoil and Fortification

With Rome’s fall, Ostrogoths and Franks occupy the area. 'A Castello' grows into a fortified borgo, providing refuge and services for travelers along ancient trade routes.

700-740 AD

Canonry is Born

Under Longobard rule, 'a Castello' becomes an Augustinian Canonry. A large proto-Romanesque church and rare octagonal baptistery are constructed.

990 AD

The Pilgrims’ Road

Archbishop Sigeric documents the Via Francigena. 'A Castello' stands as the major ecclesiastical stop between Siena and San Gimignano, hosting countless pilgrims.

1200 AD

Peak Medieval Prosperity

With 180 inhabitants, 'a Castello' thrives. Its 22 dependent churches serve travellers, the sick, and the poor, helping maintain crucial medieval routes.

1943-45

War Refuge

During WWII, 'a Castello' shelters about 60 people fleeing conflict, a quiet bastion once more.

1400-1401

Destruction and Decline

Florentine forces sack 'a Castello'. The community flees. Lands are seized; 'a Castello' is reduced to a simple parish church and farmstead.

1348

Black Death Strikes

The Plague devastates Siena and surrounding lands. 'A Castello' and its networks suffer heavy losses, marking the end of an era of prosperity.

1750-1900

Quiet Centuries

Tenant farmers like the Uzielli family work the land. By 1900, only 66 people remain at Pieve a Castello, living a simple, isolated life.

1955

Abandonment

The last priest departs. The ancient buildings fall into decay, battered by time but structurally intact thanks to centuries of sturdy construction.

1986

Rescue Mission Begins

Christopher Whinney purchases the derelict Pieve a Castello, beginning years of careful restoration under strict heritage laws.

2002

Triumph of Restoration

Pieve a Castello's restoration is completed, winning the prestigious ‘World Legacy Award’ for Heritage Tourism. Once more, it opens its doors to travelers.

Present Day

A Living History

Still offering hospitality after 1,300 years, Pieve a Castello stands preserved - a rare living link to Europe’s ancient, medieval, and modern past.

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We look forward to welcoming you!

A relaxed ‘house party’ style is consistent across the itineraries based at Pieve a Castello, which is also available to host private groups.

For an overview on 2025/2026 Tour Dates and Prices:

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