Siena, San Gimignano and Volterra: The Medieval Tuscan Triangle

The triangle of territory between Florence, the sea and the Apennines preserves a medieval landscape of completeness found nowhere else in Italy. Three cities in particular — Siena, San Gimignano and Volterra — represent the summit of what the Italian city-state achieved in stone, paint and civic organisation.

Siena does not prepare you for the Piazza del Campo. You walk through the medieval streets of the historic centre — the narrow, steep lanes of the terzo di Città, the pale Sienese Gothic of the palaces — and then you turn a corner and there it is: the great scallop-shell space of brick and sky, sloping toward the Palazzo Pubblico and the soaring Torre del Mangia, surrounded on three sides by unbroken medieval palace facades that have changed in no essential since the fourteenth century. The Piazza del Campo is one of the great achievements of medieval civic design, and it is still in active use as a public space, a political stage and, twice a year, a racetrack — which is to say that Siena has maintained a relationship with its own history that is genuinely alive rather than merely preserved for visitors.

The Palio di Siena — the bareback horse race that takes place on the 2nd of July and the 16th of August in the Campo, ten horses representing the city's seventeen contrade (historic civic districts), three laps of the piazza in ninety seconds, the most intense and most politically serious civic spectacle in Italy — is an experience that requires access to understand. From the ground level in the Campo, the race is a brief confusion of horses and jockeys and crowd noise. From the private windows and balconies of the palaces that line the Campo — the most coveted seats in Italian social life — the full architecture of the event is visible: the procession of the medieval banners, the blessing of the horse in the contrada church that morning, the political alliances and betrayals between contrade that have been accumulating for months, the specific drama of a race in which the horse wins, not the rider, and in which a riderless animal can cross the finish line first and be celebrated as a champion. We arrange these private

Palio windows through long-established relationships with the families who own the relevant properties, and we provide the contextual preparation — three evenings of dinner with a Sienese historian — that allows the race itself to be understood rather than merely witnessed.

The Duomo and the Paintings of the Sienese School

The Siena Duomo — its facade a soaring composition of white and black Sienese marble in the Italian Gothic style, its interior adorned with the Piccolomini Library frescoes by Pinturicchio and the extraordinary inlaid marble floor whose fifty-six panels, carved by generations of Sienese artists between 1372 and 1547, constitute the most elaborate decorative floor in any Italian church — is visited in the early morning with a specialist guide before the day-visitors arrive. The Museo dell'Opera del Duomo contains the Maestà of Duccio di Buoninsegna — painted in 1308–11 as the altarpiece for the Duomo and carried through the streets of Siena in a civic procession at its completion — which is the founding document of the Sienese painting tradition and one of the supreme achievements of Italian medieval art.

San Gimignano: The Towers and the Vernaccia

San Gimignano's fourteen surviving medieval towers — built between the twelfth and fourteenth centuries by competing noble families as demonstrations of wealth and political power, out of an original seventy-two — make it one of the most immediately recognisable skylines in Italy. The town is small and entirely walkable; the Collegiate church contains a fresco cycle by Ghirlandaio in the Chapel of Santa Fina that is one of the finest examples of late fifteenth-century narrative painting in Tuscany; and the Vernaccia di San Gimignano DOCG — Italy's first DOC wine, designated in 1966 — in its finest modern expressions achieves a mineral, slightly saline character that makes it the ideal companion to the local food. We include a private tasting at one of the leading estates and a private evening visit to the towers by arrangement with the municipal authorities.

Volterra: The Etruscan City and Its Alabaster

Volterra occupies a ridge of geological drama above the converging valleys of the Era and the Cecina, its pale grey tufa walls and its Etruscan Museo Guarnacci making it the most archaeologically rich and the least touristically developed of the three cities in this itinerary. The Ombra della Sera — the extraordinary elongated bronze figurine of the third century BC, one of the most haunting objects in Etruscan art, whose attenuated proportions Alberto Giacometti cited as a direct influence on his own sculpture — is in the Museo Guarnacci and visible at close range in conditions of extraordinary intimacy. The alabaster workshops of the town, producing objects from the same local stone since the Etruscans first worked it, are visited for a private demonstration of the carving technique and for the opportunity to commission a unique piece in a tradition of genuinely ancient continuity.

The Palio, seen from the private window of a Campo palazzo on the morning of the race, with a Sienese historian beside you explaining what is politically at stake between these ten horses — it is among the most completely Italian experiences we know how to design.

The Essentials

Best season: July 2 and August 16 for the Palio (book 12 months ahead); spring for the Crete Senesi landscape

Signature experience: Private Palio window with advance historical preparation; Volterra after-hours alabaster workshop visit

Stay: Siena historic-centre hotels or a converted farmhouse in the Crete Senesi

Combine with: The Val d'Orcia wine route (one hour south), Florence (one hour north)

Every journey we design is entirely bespoke — crafted around your preferences,your pace, and your desire for the exceptional.

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