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Chianti
A Renaissance villa in the hills above San Casciano, with an open-air theatre and the dome of Florence Cathedral on the horizon.
Villa La Tavernaccia is a classic Renaissance villa on a hilltop in San Casciano Val di Pesa, with 360-degree views across the Chianti hills and the dome of Florence Cathedral on the horizon. The estate is wrapped in cypress and umbrella pines, with panoramic walking paths cut through a private park, a tennis court, an open-air theatre, and a heated swimming pool that has been part of the property's history for a hundred years.
Eight bedrooms accommodate sixteen guests, all en-suite — two with twin beds, six with king-size — and the interiors blend antique pieces with contemporary furnishings, anchored by a Belvedere living room that takes in the entire valley. Prince Charles and Lady Diana stayed on the estate on their first trip to Italy in 1986. Florence is five miles away, the Siena highway is a short hop, and most of Tuscany is within an hour.
King bedroom with en-suite bathroom
King bedroom with en-suite bathroom
King bedroom with en-suite bathroom
King bedroom with en-suite bathroom
King bedroom with en-suite bathroom
King bedroom with en-suite bathroom
Twin bedroom with en-suite bathroom
Twin bedroom with en-suite bathroom
Property
Villa La Tavernaccia sits 300 metres above sea level on a hilltop in San Casciano Val di Pesa, on a private park planted with cypress and umbrella pines. The grounds include a large heated swimming pool (a century of history on the property), a private tennis court, an open-air theatre with a sight-line to the dome of Florence Cathedral, and multiple panoramic walking routes through the estate. Views run 360° across the Chianti valleys toward Fiesole, Panzano, and Volterra.
Living spaces
A Belvedere living room with a 360° valley view, a second living room, a formal dining room, and a fully-equipped kitchen — anchored by antique furnishings woven through contemporary pieces.
Bedrooms
Eight double bedrooms, all en-suite — six with king beds and two with twins (see Rooms).
Outdoors
Heated swimming pool. Private tennis court. Open-air theatre. Multiple panoramic walking paths. Cypress and umbrella pine landscaping across the private park.
Heritage
A classic Renaissance villa; a photograph in the family archive dates the pool to 1930. Prince Charles and Lady Diana stayed on the estate on their first trip to Italy in 1986. The interiors blend antique furnishings with contemporary pieces — designed to feel timeless rather than themed.
Electricity, A/C, water, gas; final cleaning
Daily housekeeping up to 4 hours (Sundays off)
Garden, pool and tennis court maintenance
Wi-Fi indoor and outdoor
On request: private cook, in-villa wine tastings of Chianti producers, cooking classes, tennis lessons, transfers
Children welcome
No pets
No smoking inside
Check-in 4pm · check-out 10am
Your concierge can help arrange unforgettable experiences tailored to your stay.
Chianti
A morning at a small Chianti Classico producer — Castello di Ama, Felsina, Fontodi, or a family estate without a sign on the road. Cellar tour, four wines, and lunch with the winemaker.
Chianti
A nonna and a long wooden table. Fresh pici, ribollita, tiramisu, and a bottle of the house red. Half a day, ending with the meal you made.
Chianti
An hour east toward Casentino with a truffaio and his Lagotto Romagnolo. Two hours of slow walking in the woods, then truffle pasta for lunch at the farm.
Chianti
The two-lane road from Florence to Siena that threads through every postcard view of Chianti. Sixty kilometres, half a day if you stop for lunch, a whole day if you stop for tastings.
Chianti
Late October and early November. Pick olives in the morning, watch them go into the press in the afternoon, taste the green-gold oil within hours of pressing.
Chianti
Saturday and Tuesday mornings in Piazza Matteotti. Cheeses, cured meats, fresh ricotta, vegetables from the surrounding farms — the building block of every great Tuscan dinner.
Villa La Tavernaccia sits on a hilltop in San Casciano Val di Pesa, with 360° Chianti views and the dome of Florence Cathedral on the horizon — about 5 miles from Florence and 40 miles from Siena.
Travel Advisor
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