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Castelfalfi

Five-star · From $600 per nightAny mandatory hotel fees are shown before you confirm.
First light over Chianti, Siena & Val d'Orcia
DestinationChianti, Siena & Val d'Orcia · Florence & Tuscany
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Chianti, Siena & Val d'Orcia · Florence & Tuscany

A sense of the place

Golden hour over Chianti, Siena & Val d'Orcia

Why it's in the collection

Because a whole medieval borgo, kept as an estate between Florence, Pisa and San Gimignano with golf and a spa inside it, is a place rather than a hotel – and it is run, independently, to five-star standing.

  • A medieval borgo – a hamlet – and the estate around it.
  • Between Florence, Pisa and San Gimignano, each within reach by car.
  • Golf on the estate.
  • A spa within the borgo; independently run, with Two MICHELIN Keys 2025 and five-star standing.

The neighborhood

First light over Chianti, Siena & Val d'Orcia

Chianti, Siena & Val d'Orcia

The countryside south and west of Florence, where the other three hotels are estates. It takes in Chianti's vineyards on the road to Siena, the hill towns from San Gimignano to Montalcino, and the bare, folded valley of the Val d'Orcia beyond. The estates are a winery, a borgo, and a villa with its farm.

  • San Gimignano and its towers.
  • Volterra, across the hills to the southwest.
  • Pisa, to the northwest.

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Nearby in the collection

Borgo Santo Pietro

Five-star · Chianti, Siena & Val d'Orcia

A 13th-century villa and its organic farm near Chiusdino, in the Sienese hills, independently run.

From $1,200 per night

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Rosewood Castiglion del Bosco

Five-star · Chianti, Siena & Val d'Orcia

Rosewood's 800-year-old estate above Montalcino, with its own Brunello winery, in the UNESCO landscape of the Val d'Orcia.

From $1,400 per night

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Four Seasons Hotel Firenze

Five-star · Florence Centro Storico

Palazzo della Gherardesca, Four Seasons' house in the centro storico, behind the largest private garden in Florence.

From $1,500 per night

Any mandatory hotel fees are shown before you confirm.