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Chianti
Villa Tavernaccia
A Renaissance villa in the hills above San Casciano, with an open-air theatre and the dome of Florence Cathedral on the horizon.
About This Villa
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.
Photos
Villa Tour
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
Quick answers about Villa Tavernaccia
- How many people does Villa Tavernaccia sleep?
- Villa Tavernaccia sleeps 16 guests in 8 bedrooms, with 7.5 bathrooms.
- Where is Villa Tavernaccia?
- 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.
- How much does it cost to rent Villa Tavernaccia?
- Villa Tavernaccia rents from €32,000 per week. Rates vary by season, and your Doorways travel advisor confirms the exact rate for your dates.
- What is included at Villa Tavernaccia?
- 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.
- How do I book Villa Tavernaccia?
- Book Villa Tavernaccia through Doorways Villa Vacations, a US-based, IATA-accredited agency arranging Italian villa stays since 1994. Send an inquiry with your dates, and a dedicated travel advisor replies with availability and the rate.
Inspiration to get you dreaming
Your concierge can help arrange unforgettable experiences tailored to your stay.
Chianti
Private vineyard tour and tasting
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
Cooking class at a Chianti farmhouse
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
Truffle hunt with dogs
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
Drive the Strada Chiantigiana (SR222)
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
Olive harvest at a family frantoio
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
A morning at the Greve market
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.
Availability
Pricing is per week, Saturday to Saturday. Diagonal cells mark changeover Saturdays — morning departure / afternoon arrival.
Available Booked Changeover (Saturday)
October 2026
November 2026
December 2026
January 2027
February 2027
March 2027
April 2027
May 2027
June 2027
July 2027
August 2027
September 2027
San Casciano Val di Pesa
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.
Map location is approximate. Contact us with any questions.
