Almost everyone books Florence and Siena. The Tuscany people actually picture — the cypress avenue over a hill, the farmhouse on a ridge, the light going long over a valley of wheat and vines — is not in either. It is the countryside between and south of them, and it is where the estate hotels are.
Those estates are the product of a specific history. The mezzadria sharecropping system, which had organised Tuscan farming for six centuries, was abolished in the 1960s, and thousands of farms emptied as families left for cities. The buildings sat derelict for decades. From the 1980s onward they were bought and restored, first by foreigners and later at enormous scale by hotel groups.
Where the countryside is
Chianti, between Florence and Siena, is the closest and the most developed: vineyards, stone villages and the shortest drives to both cities.
The Val d'Orcia, south of Siena, is the UNESCO landscape and the one on the postcards, around Pienza, Montalcino and San Quirico. It is emptier and about ninety minutes from Florence.
The Maremma and the southwest, toward the coast, are wilder and much less visited.
The thermal belt, around Bagno Vignoni, San Casciano dei Bagni and Saturnia, has hot springs that the Etruscans and Romans used and several serious spa hotels.
The practical constraint is driving. These estates are on unpaved strade bianche, the white gravel roads, often several kilometres from a village. That is the appeal and it means you drive to dinner, or you eat where you are staying.
The thirteen below are grouped by area.
The Val d'Orcia and Montalcino
The UNESCO landscape south of Siena.
Castiglion del Bosco, A Rosewood Hotel occupies a 1,100-hectare estate near Montalcino with a medieval village at its centre, a Brunello vineyard, a golf course and a cookery school. It is the largest and most complete estate hotel in Tuscany.
Castiglion del Bosco, A Rosewood Hotel
Montalcino, Val d'Orcia · 5★ · $$$$
Eleven hundred hectares around a medieval village
Check availabilityLupaia sits on a hilltop at Torrita di Siena with a handful of rooms in restored farm buildings, no signage and views across the Val d'Orcia. It is the most personal place to stay in southern Tuscany.
Lupaia
Torrita di Siena · 5★ · $$$$
A handful of rooms on a ridge with no signage
Search hotels in TuscanyADLER Thermae occupies a thermal property at Bagno Vignoni with pools fed by the springs the Medici used, a large spa and a medical wellness programme.
Fonteverde sits at San Casciano dei Bagni with thermal pools terraced down a hillside, a spa and views over the Val di Paglia.
Chianti and the Siena hills
Between the two cities. Vineyards and the shortest drives.
COMO Castello Del Nero occupies a fifteenth-century castle at Tavarnelle in 300 hectares with a spa, two restaurants and Chianti vineyards. It is the best-run estate in Chianti.
COMO Castello Del Nero
Tavarnelle, Chianti · 5★ · $$$$
A fifteenth-century castle in 300 hectares of vines
Check availabilityCastel Monastero - The Leading Hotels of the World sits in a restored monastery near Castelnuovo Berardenga with a spa, a pool and a wine estate, and a level of quiet its size does not suggest.
Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga · 5★ · $$$$
A restored monastery estate with a spa and a wine label
Check availabilityHotel Le Fontanelle occupies a hillside estate at Castelnuovo Berardenga with an infinity pool over the vines, a contemporary interior and a strong kitchen.
Hotel Le Fontanelle
Castelnuovo Berardenga · 5★ · $$$
Infinity pool over the vines with a strong kitchen
Check availabilityThe western hills and Volterra
Toward the coast, emptier and less visited.
Castello di Casole, A Belmond Hotel, Tuscany occupies a tenth-century castle and estate near Casole d'Elsa in 1,700 hectares, restored over years, with a spa, a golf course and a village of farmhouses.
Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa · 5★ · $$$$
A tenth-century castle on 1,700 hectares
Check availabilityBorgo Santo Pietro sits on a 130-hectare farm at Chiusdino with an organic garden, a serious restaurant, a spa and a cookery school. The food is the reason to come.
Borgo Santo Pietro
Chiusdino · 5★ · $$$$
A working farm with a serious restaurant and cookery school
Check availabilityCastelfalfi occupies a 1,100-hectare estate at Montaione with a restored medieval village, two golf courses and several pools. It is the family answer.
The Val d'Arno
East of Florence, toward Arezzo.
Il Borro Relais & Châteaux occupies a hilltop village on a 700-hectare wine and olive estate, with rooms in the restored houses, a spa and a working farm.
Il Borro Relais & Châteaux
Val d'Arno · 5★ · $$$$
A hilltop village on a 700-hectare wine estate
Check availabilitySiena itself
For a night in the city.
Grand Hotel Continental Siena - Starhotels Collezione occupies a sixteenth-century palace on the Banchi di Sopra with a frescoed hall and rooms minutes from the Campo. It is the only five-star hotel inside Siena's walls.
Grand Hotel Continental Siena - Starhotels Collezione
Inside Siena's walls · 5★ · $$$$
The only five-star inside the walls, minutes from the Campo
Check availabilityHotel Certosa Di Maggiano sits in a fourteenth-century monastery just outside the walls with a garden, a pool and a cloister.
Hotel Certosa Di Maggiano
Outside Siena's walls · 5★ · $$$$
A fourteenth-century monastery with a cloister and pool
Check availabilityWhat we have left off
The agriturismi and villa rentals across Tuscany are excluded, and they are how the great majority of visitors stay in the countryside, particularly for a week with a family. They are farm stays and houses rather than hotels.
What to do
Drive the Val d'Orcia between Pienza, San Quirico and Montalcino at either end of the day, when the light does what it does in the photographs.
Do a Brunello tasting at Montalcino and a Vino Nobile at Montepulciano, both by appointment.
See Siena's Campo and the cathedral, and go early. If you are there on 2 July or 16 August, the Palio fills the city entirely.
Walk part of the Via Francigena, the medieval pilgrim road from Canterbury to Rome, which runs through this landscape and is waymarked.
Eat pici, ribollita, bistecca alla fiorentina if there are two of you, and pecorino from Pienza.
Practical notes
Florence and Pisa both have airports; Rome is two and a half hours from the Val d'Orcia. A car is essential and the gravel roads are slower than the map suggests.
May, June, September and October are ideal. July and August are hot and busy. Winter is quiet and many estates close from November to March.
Book restaurants and cellar doors ahead in the countryside; the good ones are small and often family-run.
Explore 4 & 5 Star Tuscany Hotels
Questions people actually ask
Countryside or city?
The countryside is the Tuscany people picture. Florence and Siena are day trips from it, not the other way round.
How far are the estates from anything?
Often several kilometres down gravel roads. You drive to dinner or you eat at the hotel.
Chianti or the Val d'Orcia?
Chianti for proximity to both cities, the Val d'Orcia for the landscape. Ninety minutes apart.
How many nights?
Seven. Five in the countryside and two in Florence or Siena.