A pope’s nephew and a staircase with a dark legend. A castle with its own theatre. A film director’s party house. Three historic hotels in Tuscany where the stories are as good as the views.
Historic hotels in Tuscany are not in short supply. What it has fewer of are places where the history is specific, a little strange, and still in the walls.
These three came up in this week’s Shortlist. All are in the countryside around Siena, and all of them can be booked.
Villa Cetinale: the cardinal and the staircase
Cetinale sits in the hills west of Siena, at the end of a long avenue of cypresses. It was the country retreat of Cardinal Flavio Chigi, nephew of Pope Alexander VII, who brought in Carlo Fontana, a pupil of Bernini, to remodel it in the Roman Baroque style from 1680.
The villa’s most famous feature is outside. A steep stone staircase, the Scala Santa, climbs the hill on the villa’s main axis to a hermitage at the top. Local legend says the cardinal was sentenced to climb it on his knees as penance for a killing. There is no evidence he ever killed anyone, and locals also say he probably climbed it about once a year, and certainly not on his knees.
The Chigi family kept Cetinale for three centuries. By 1977 it was falling apart when the British politician Lord Lambton bought it and spent the rest of his life restoring the house and gardens. His family still owns it, and the villa can now be rented privately.
The best stories are the ones nobody can prove. This one comes with a Baroque garden attached.
Castello di Meleto: a border castle with its own stage
Meleto stands on a hilltop just south of Gaiole in Chianti, above the old road between the Valdarno and Siena. A branch of the Ricasoli family held it for centuries, and it was the last Florentine stronghold before Sienese territory. Despite that position, it never suffered serious destruction.
In the 18th century the Ricasoli turned the fortress into a country house and farm. Their best addition is hidden inside: a tiny private theatre from the 1740s, complete with its seven original painted sets. It’s on the guided tour, along with the frescoed rooms and the cellars where Vin Santo is still aged.
Today Meleto is a working Chianti Classico estate. Guests stay in rooms in the castle itself, with four-poster beds and beamed ceilings. One warning from a past guest: the tower staircase is very narrow, so pack light.
Most castles have a ghost story. This one has a stage.
Castello di Casole: the Visconti party house
Casole sits between Siena and San Gimignano, in the hamlet of Querceto, named after the oak woods around it. The castle dates back to the 10th century, and the Bargagli family later made it the centre of a large farming estate.
In the late 1950s, the Bargagli heirs sold it to Edoardo Visconti, brother of the film director Luchino Visconti. Through the 1960s the brothers made it a retreat for the film world, with Luchino entertaining guests such as Sophia Loren and Helmut Berger.
Belmond bought the estate in 2018 and runs it as a 39-room hotel on 1,500 acres of farmland, vineyards and olive groves. The bar is named Bar Visconti and is hung with stills from his films.
Come for the 1,500 acres of quiet. Stay for the bar.
Worth knowing this week
- Rosewood’s rare 30% sale ends on 10 November. The Rosewood Beyond offer takes 30% off the best available rate at participating hotels, plus a perk at each, for stays until 30 June 2027. You can only book it through a Rosewood Elite travel advisor, not directly with the hotel, and villas and houses are excluded.
- Half of under-35s would let AI book their trip. The WTM Global Travel Report found 54% of 18 to 34-year-olds trust AI to complete a booking, against 18% of over-55s. Booking.com says daily AI search visitors rose tenfold in a quarter, yet AI platforms still drive less than 1% of its room nights. Lots of people are asking the chatbot. Very few are letting it pay.
Until next time
None of these three will ever top a list of Tuscany’s newest hotels. That’s rather the point.
For five more stories worth knowing, see The Shortlist. And for another castle with a royal fugitive in its past, read Alone in a 16th-century Scottish castle.
