🫒Città dell'Olio in Tuscany

Montalcino

Province: Siena · 564 m

• 🍷Brunello di Montalcino DOCG

A walled hill town at 564 meters above the Val d'Orcia, the last fortress to hold out for the Sienese Republic and the birthplace of Brunello.

Massa Marittima

Province: Grosseto · 380 m

A medieval mining town at 380 meters in the Colline Metallifere, free commune from 1255 to 1337, whose cathedral holds the relics of San Cerbone.

San Casciano dei Bagni

Province: Siena · 582 m

A hilltop borgo at 582 meters above 42 hot springs that produced the largest Etruscan bronze hoard of the last fifty years.

San Gimignano

Province: Siena · 334 m

A walled hill town at 334 meters with 14 surviving medieval towers, UNESCO listed since 1990 and the home of Vernaccia.

Suvereto

Province: Livorno · 127 m

A stone borgo at 127 meters above the Val di Cornia, named for the cork oaks of its forests and ruled from the Rocca Aldobrandesca since 973.

Capalbio

Province: Grosseto · 217 m

A walled hilltop borgo at 217 meters in the southern Maremma, donated to the Abbey of Tre Fontane by Charlemagne and home of Niki de Saint Phalle's Tarot Garden.

Castagneto Carducci

Province: Livorno · 194 m

A hilltop borgo at 194 meters above the Costa degli Etruschi, renamed for the poet Carducci in 1907 and the home of Bolgheri and Sassicaia.

Castelnuovo Berardenga

Province: Siena · 351 m

• 🍷Chianti Classico DOCG

A Chianti Classico commune at 351 meters between the Ombrone and the Crete Senesi, the last castle Siena built against Florence, in 1366.

Castiglione d'Orcia

Province: Siena · 540 m

A stone borgo at 540 meters in the UNESCO Val d'Orcia, first recorded in 714, with two fortresses guarding the road from Amiata to the Via Francigena.

Cetona

Province: Siena · 384 m

A medieval borgo at 384 meters below Monte Cetona, sold by Cosimo I to the Vitelli in 1556 and the centro storico still shaped by their fortress reconstruction.

Lucignano

Province: Arezzo · 400 m

A walled elliptical hill town at 400 meters between Siena and Arezzo, planned in medieval concentric rings around the goldsmith's reliquary called the Tree of Life.

Manciano

Province: Grosseto · 444 m

A market town at 444 meters in the southern Maremma, with a Sienese fortress of 1424 and the thermal frazione of Saturnia in its territory.

Montaione

Province: Firenze · 341 m

A medieval glassmaking and truffle borgo at 341 meters above the Valdelsa, with a Franciscan replica of Jerusalem in the woods at San Vivaldo.

Montepulciano

Province: Siena · 605 m

• 🍷Vino Nobile di Montepulciano DOCG

A Renaissance hill town at 605 meters on a limestone ridge, where Vino Nobile is aged in vaulted cellars beneath the palazzi of Piazza Grande.

Montescudaio

Province: Pisa · 242 m

A fortified hill borgo at 242 meters above the Val di Cecina, named for a mountain of shields, with DOC wine since 1977 and bread, oil and grape all stamped in its identity.

Pitigliano

Province: Grosseto · 313 m

The Little Jerusalem of southern Tuscany, carved into a tuff spur in the Maremma, where the houses, the synagogue and the streets are all cut from the same volcanic rock.

San Quirico d'Orcia

Province: Siena · 409 m

A walled stop on the Via Francigena at 409 meters in the UNESCO Val d'Orcia, where a twelfth-century Collegiata, a Renaissance garden and the Bagno Vignoni thermal pool sit within fifteen kilometers of each other.

Siena

Province: Siena · 322 m

The medieval rival of Florence at 322 meters on three hills, with a shell-shaped piazza where seventeen contrade race bareback horses twice a year.

Castellina in Chianti

Province: Siena · 578 m

• 🍷Chianti Classico DOCG

A Chianti hill town at 578 meters on the watershed between the Arno and the Ombrone, with an Etruscan tumulus, a Brunelleschi-reinforced wall and a covered medieval walkway around its edge.

Castiglion Fiorentino

Province: Arezzo · 342 m

A walled hill town at 342 meters between Arezzo and Cortona, where Etruscan walls support the medieval Cassero and Vasari's loggia frames the Val di Chiana below.

Chiusi

Province: Siena · 398 m

The Etruscan city of King Porsenna at 398 meters above the Val di Chiana, with one of Italy's major Etruscan museums and tunnels carved beneath the streets.

Greve in Chianti

Province: Firenze · 236 m

• 🍷Chianti Classico DOCG

The market town of the Chianti Classico zone on the Greve river, with a triangular piazza arcaded since the sixteenth century.

Monteriggioni

Province: Siena · 274 m

A circular Sienese fortress built between 1213 and 1219 on a natural hill, fourteen towers on a 570-meter wall, intact and unbroken.

Murlo

Province: Siena · 314 m

A medieval bishops' fief twenty kilometers south of Siena, with an Etruscan princely palace on Poggio Civitate and the Cappellone statue as its symbol.

Pienza

Province: Siena · 491 m

The first Renaissance ideal city, built from 1459 by Bernardo Rossellino for Pope Pius II on the Val d'Orcia ridge.

Rapolano Terme

Province: Siena · 334 m

A Sienese thermal town in the Crete Senesi, 38-degree calcium-sulphur waters and travertine quarries that supplied the Pienza Duomo and Montepulciano's San Biagio.

Vinci

Province: Firenze · 97 m

The hill town on Montalbano where Leonardo was born in 1452, with a ship-shaped castle that now holds his machines.

Chiusdino

Province: Siena · 564 m

A medieval village at 564 meters in the Val di Merse where Galgano Guidotti plunged his sword into a rock in 1180 and the roofless Cistercian abbey grew up below.

Cortona

Province: Arezzo · 494 m

An Etruscan lucumonia at 494 meters with two kilometers of walls older than Rome, looking down on the Val di Chiana and Lake Trasimeno.

Fiesole

Province: Firenze · 295 m

An Etruscan hilltop at 295 meters above Florence, founded in the ninth century BC and conquered by Rome in 283 BC, still looking down on what later replaced it.

Piancastagnaio

Province: Siena · 772 m

A chestnut-belt borgo at 772 meters on the southern slope of Monte Amiata, where four contrade still race for the Palio delle Contrade each August.

Trequanda

Province: Siena · 453 m

A village of 1,166 in three hilltop borghi between Crete Senesi and Val di Chiana, with the terracotta workshops of Petroio holding to a five-hundred-year craft.

Vicopisano

Province: Pisa · 12 m

A medieval river port on the southern slope of Monte Pisano, rebuilt by Brunelleschi in 1434 after Florence took the town from Pisa.