TuscanyArea guide
A hill town above the Val di Chiana, with countryside villas and access to eastern Tuscany and nearby Umbria.
2 villas in Cortona in our collection, sleeping 12 to 18 guests; every one has a private pool and 1 list a heated pool. The largest, Villa della Cappella, sleeps 18. A private chef can be arranged at every villa.
2 villas in the collection
2 villas
Cortona · 18 guests · 9 bedrooms
From €10,150 / week
Private chapel · Frescoed interiors
A genuine 17th-century restoration: frescoed vaulted ceilings, painted walls and terracotta floors across more than 1,000 square…
Cortona · 12 guests · 7 bedrooms
From €20,700 / week
Private chef · Infinity pool
More than seventy fenced acres of its own, meadows, olive groves, a deer park, woodland walks and a private lake.
On Cortona
Cortona is the Etruscan city on the hill at Tuscany's eastern edge, looking across the Val di Chiana to Lake Trasimeno and Umbria beyond. It is one of the oldest continuously inhabited towns in Italy, and its museum, the MAEC, holds the proof: the Tabula Cortonensis, a bronze tablet carrying one of the longest Etruscan inscriptions ever found. A film made the town globally famous in 2003; the town, to its credit, went back to being itself, and the visitors who come now find a working hill town with an unusually good kitchen.
The eating is the Val di Chiana's doing: this is chianina country, the white cattle behind the bistecca alla fiorentina, and the trattorie here serve it closer to the source than anywhere else in Tuscany. From our Val d'Orcia estates Cortona is about fifty minutes, the natural far-eastern day of a week, often paired with Montepulciano on the road home.
A villa stay around Cortona and a day trip to Cortona are different plans. If you want several meals in town, ask about the actual road from the villa, where you would park and the walk to your chosen restaurant. If you are visiting once from another base, give the town its own unhurried day rather than attaching it to several other hill towns.
The slopes are part of the setting, but they matter for children, pushchairs and anyone with limited mobility. Agree a comfortable route for the group and allow people to separate for a museum or a longer climb. Back at the villa, a shaded outdoor dining area and comfortable indoor seating give the group somewhere to reunite without another outing.
The Museo Diocesano keeps a Fra Angelico Annunciation that would be mobbed in Florence and is usually contemplated here in near silence. Above the town, the basilica of Santa Margherita holds Cortona's own thirteenth-century saint, and the steep walk up past the Via Crucis buys the whole Val di Chiana at your feet, with Trasimeno silver in the distance. Come in the cool of the morning, as the locals do; Cortona's streets are vertical and unapologetic about it.
When to come
May, June, September and October. Cortona's height keeps summer evenings pleasant even when the Chiana floor bakes; February belongs to the town itself around Santa Margherita's feast.
Towns worth knowing
Best for
Practicalities
Park at the Santo Spirito or Parterre lots and walk in; the streets are not for cars. The Camucia-Cortona station below town is on the Florence-Rome line, one of the few hill towns the train serves usefully.
Frequently asked
Compare nearby areas and alternative bases
Planning the week