Tuscany and Umbria Estates
The Italian country estate: usually a working farm or a restored hamlet with a hotel inside it, in the Val d'Orcia, Chianti, the Maremma or the Umbrian hills. What you are paying for is land, meaning vines and oak in every direction, a pool with nothing overlooking it, and a white road you would rather not drive after two glasses. We rank on how far it is to a town you would actually want dinner in, on whether the wine and oil are made on the property or bought in, on how the estate copes with weddings and families in July, and on what the rooms are like inside old stone, which can mean small windows and modest air conditioning. Coastal Italy has its own list.
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A fifteenth-century Franciscan monastery in the Fiesole hills above Florence with a Renaissance facade traditionally attributed to Michelangelo, restored beginning in 1988 and set within terraced olive groves and gardens that overlook the Arno valley.
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A 5,000-acre Val d'Orcia estate where you stay in 17th-century farmhouses and eat in a Michelin-starred restaurant while the property produces historic Brunello di Montalcino wine and hosts truffle hunts through its own woods.
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A seasonal Belmond hotel on an ancient Etruscan site with 30 acres of olive groves producing only 2,500 bottles annually of private-label oil, plus organic vineyards making Ulpaia wines used in its restaurants.
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A 300-acre certified organic farm estate with a Michelin-starred restaurant built on soil-to-plate cuisine from its own market gardens, dairy, and livestock, near Siena.
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An organic agricultural estate in the Montaione countryside with multiple pools surrounded by vineyards and olive groves, producing its own wines and oils.
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A 1,100-hectare certified organic estate producing its own wines and extra virgin olive oil, with four restaurants guided by Executive Chef Andrea Campani cooking from the farm's vegetables, vineyards, and groves.
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A thousand-year-old castle and 3,700-acre estate in the Umbrian hills, restored from ruin over three decades by the Bolza family into a living community of 50 rebuilt farmhouses, chapel, and original fortifications.
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A medieval hamlet dating to the eighth century, restored in the late twentieth century within the Chianti Classico hills, with an intact piazza, chapel, and winding lanes that once housed a school, bakery, and mill, surrounded by the estate's own vineyards.
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A 12th-century castle in the wild Maremma, reached by a mile-long dirt road through vineyards and oak forest, surrounded by 40 hectares of organic estate vineyards and olive groves.
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A twelfth-century Tuscan castle layered with Renaissance frescoes and medieval stone, restored with contemporary interiors by Paola Navone, set within a 740-acre estate producing its own wine and olive oil.
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An eighteenth-century villa in the Volterra countryside with organic vineyards, estate production, and rooms in a restored historic mansion, located on rolling Tuscan hills.
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An 11th-century castle hotel perched on a hilltop 10 kilometers south of Montalcino, surrounded by its own Brunello di Montalcino vineyards, with no other settlement visible from the rooms.
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A 15th-century villa in the Fiesole hills above Florence, set across twelve hectares of parkland. Rooms blend old stone with contemporary comfort, each one different, each one looking either down the Arno valley or into Italian gardens.
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A luxury hotel built into a restored village in the Val d'Orcia, accessed only by gravel roads and designed so the car park is a five-minute walk from the rooms, enforcing a quiet, footpaced arrival.
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A historic estate in Panzano in Chianti with rooms spread across the villa, outbuildings, and apartments. Exposed beams, Italian terracotta, air conditioning you control, and the accumulated texture of a property that was built to be lived in by families, not hotels.
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A 12-room farm estate dating to 1622, perched on a Tuscan hilltop between Montepulciano and Pienza, reached by a 3-kilometer scenic gravel track through vineyards and olive groves.
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Six rooms and suites in a restored Tuscan farmhouse in a valley south of Siena. Loft-like spaces with three-window exposures, concrete floors, air conditioning you control, and views of grain fields and distant hills.