🟠Bandiera Arancione 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.

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.

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.

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.

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.

Anghiari

Province: Arezzo · 430 m

A walled medieval town at 430 meters over the upper Tiber valley, where Florence beat Milan in 1440 and Leonardo started the fresco he never finished.

Barga

Province: Lucca · 410 m

A medieval hilltop town at 410 meters in the Serchio valley between the Apuan Alps and the Apennines, where Giovanni Pascoli wrote his last poems and the August festival serves fish and chips.

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.

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.

Peccioli

Province: Pisa · 144 m

Borgo dei Borghi 2024 in the Valdera hills, a medieval village that funded a public contemporary-art program with revenue from its landfill plant.

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.

Radicofani

Province: Siena · 814 m

The Val d'Orcia's basalt watchtower — a 1,060-resident UNESCO-inscribed borgo at 814m on a volcanic basalt outcrop visible across half of southern Tuscany, with the spectacular Rocca di Radicofani (Ghino di Tacco's outlaw fortress, mentioned by Dante in Purgatorio + Boccaccio in the Decameron), the 16th-c Posta Medicea on the Via Francigena, and Bandiera Arancione + UNESCO + Via Francigena triple signal.

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.

Abetone Cutigliano

Province: Pistoia · 1,388 m

The Apennine ski pass at 1,388 meters where the Granduca's two stone pyramids of 1778 mark the old Tuscan-Modenese border.

Casale Marittimo

Province: Pisa · 214 m

A concentric stone borgo at 214 meters above the Val di Cecina, built where a seventh-century BC Etruscan outpost of Volterra once stood.

Certaldo

Province: Firenze · 67 m

The brick-built upper town in the Valdelsa where Boccaccio spent his last years, twenty-five kilometers from Florence on the medieval road to Siena.

Montecarlo

Province: Lucca · 163 m

A walled hill village at 163 meters above the Lucca plain, founded by Emperor Charles IV in 1333 and named for him, surrounded by twenty wineries.

Santa Fiora

Province: Grosseto · 687 m

An Aldobrandeschi and Sforza mountain borgo on Monte Amiata at 687 meters, holding one of the world's largest collections of Della Robbia terracotta.

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.

Volterra

Province: Pisa · 531 m

The Etruscan acropolis of Velathri at 531 meters, the alabaster town that has been carving the same stone for three thousand years.

Castelnuovo di Val di Cecina

Province: Pisa · 576 m

A copper and geothermal borgo at 576 meters in the Cecina valley, where natural steam vents and medieval towers sit on the same hill.

Fosdinovo

Province: Massa-Carrara · 500 m

The southern Lunigiana stronghold at 500 meters, the Malaspina castle where Dante took shelter in 1306 and later set a Purgatorio canto.

Pomarance

Province: Pisa · 369 m

The capital of the Tuscan geothermal field at 369 meters, where industrial steam plumes rise from the same hills that produced two Renaissance painters.