The 7 best hill towns in the province of Firenze

1. Montaione

Best for a soak. The comune has thermal baths.

1 h 7 min from Florence · homes €1,000 to €1,500 a m² in the center · 3,438 people

Why visit Montaione

Montaione sits at 341 meters on a ridge above the Valdelsa, in the wooded hills west of Florence on the road toward Volterra. Etruscan and Roman finds at Poggio all'Aglione, Bellafonte and Iano confirm continuous occupation across the territory, material now held in the town's archaeological museum.

The medieval castello was the seat of an autonomous comune from 1256 and passed to Florence in 1369. From the early fourteenth century, glassmaking ran in the surrounding woods, and an eighteenth-century decree by the Grand Duke required master glassmakers to teach the craft to their fellow citizens.

The town joined Borghi più belli in 2007. The territory spreads well beyond the ridge itself.

Five kilometers west, a Franciscan convent founded in 1500 stands in the woods, its chapels laid out as a walkable replica of Jerusalem's holy sites. Ten kilometers south, Castelfalfi carries a separate, older Lombard origin, now a resort with its own vineyards and church.

Between them, the centro storico keeps the civic core: the tower, the palace, the parish church rebuilt on twelfth-century foundations. The comune, in effect, holds three distinct centuries of settlement at once: an ancient scatter of finds, a fourteenth-century craft economy, and a devotional complex from the 1500s, spread across ridge, castle and wood rather than gathered in one place.

What to see in Montaione

• Sacro Monte di San Vivaldo. Complex five kilometers west of the borgo. Seventeen chapels stand among oak woods, each holding a scene built as part of the topographical replica, still reached on foot along the paths between them.
• Castelfalfi. Lombard-origin castle and frazione ten kilometers south, restored as a private resort with vineyards and a Romanesque church of San Floriano.
• Centro storico. Medieval grid on the ridge, with the Palazzo Pretorio, the Torre del Cassero and the Chiesa di San Regolo restored after 1118 foundations.

How to get to Montaione

Florence is about 1 h 7 min away by road.

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2. Cerreto Guidi

Best for a World Heritage site. UNESCO lists a site in the comune.

50 min from Florence · homes €1,000 to €1,500 a m² in the center · 10,663 people

Why visit Cerreto Guidi

Cerreto Guidi sits at 123 meters above the Padule di Fucecchio, thirty kilometers west of Florence, on the old hunting grounds of the Counts Guidi and later the Medici. Cosimo I commissioned the Villa Medicea here between 1564 and 1567 as a hunting lodge and territorial outpost over the marsh.

The villa is mounted on a scenographic base of four symmetrical ramps of stairs, the ponti medicei, traditionally attributed to Bernardo Buontalenti, designed to raise the perspective plane and the level of the entrance. In 2013 the villa entered the UNESCO list of Medici Villas and Gardens of Tuscany along with twelve others, and it remains one of the few permanently open as a museum, housing the Museo Storico della Caccia e del Territorio since 2002.

The Via Francigena passes a few kilometers south. Isabella de' Medici, daughter of Cosimo I, was strangled in this villa by her husband Paolo Giordano Orsini in July 1576.

What to see in Cerreto Guidi

• Villa Medicea di Cerreto Guidi. Hunting villa built for Cosimo I de' Medici between 1564 and 1567, UNESCO World Heritage since 2013, holding the Museo Storico della Caccia.
• Ponti Medicei. Four symmetric ramps of stairs attributed to Buontalenti, supporting the villa above the village and forming its scenographic base.
• Museo Storico della Caccia e del Territorio. Hunting and local history museum housed in the villa since 2002, with weapons, prints and documents from the Medici hunting grounds.

How to get to Cerreto Guidi

Florence is about 50 min away by road.

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3. Barberino di Mugello

Best for a day out from Prato. It is 34 min by car.

34 min from Prato · homes €1,300 to €1,900 a m² in the center · 10,939 people

Why visit Barberino di Mugello

Barberino di Mugello sits at 272 meters in the upper Sieve valley, twenty-five kilometers north of Florence, the road and rail gateway from the city to the Mugello and onward to Bologna across the Apennines. The Medici family had its roots in this territory: Cosimo the Elder commissioned Michelozzo around 1451 to transform the medieval castle at Cafaggiolo into a country villa, the first in the Medici building campaign that would later run through Poggio a Caiano and Cerreto Guidi.

In 2013 Villa di Cafaggiolo and the nearby Villa del Trebbio joined eleven other Medici properties on the UNESCO list. Michelozzo's hand also shows on the fifteenth-century loggia in the main piazza of Barberino.

South of the town lies the Lago di Bilancino, an artificial reservoir completed in 1999, the largest in Tuscany at five square kilometers, built to feed the water supply of Florence, Prato and Pistoia, and now used for sailing, windsurfing and birdwatching.

What to see in Barberino di Mugello

• Villa Medicea di Cafaggiolo. Medieval castle transformed into a country villa by Michelozzo around 1451 for Cosimo the Elder, UNESCO World Heritage since 2013.
• Villa Medicea del Trebbio. Smaller medieval Medici castle on a wooded hilltop near San Piero a Sieve, also inscribed on the UNESCO list of Medici Villas in 2013.
• Lago di Bilancino. Artificial reservoir completed in 1999, five square kilometers, the largest in Tuscany, built to supply Florence, Prato and Pistoia.

How to get to Barberino di Mugello

Prato is about 34 min away by road.

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4. Greve in Chianti

Best for Chianti Classico DOCG. The town gives its name to Chianti Classico DOCG.

44 min from Florence · homes €1,500 to €2,100 a m² in the center · 13,381 people

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Why visit Greve in Chianti

Greve sits at 236 meters in the Val di Greve, thirty-one kilometers south of Firenze and forty-two north of Siena, on the small fast river that gave the town its name. The valley narrows here enough that the road to Firenze runs past the castle estates on the slopes to the north before dropping into the town itself, and the walled hamlet above Greve looks down on the piazza from its kilometer of higher ground, a settlement some centuries older than the square below it, its tenth-century walls predating the piazza's sixteenth-century arcades.

The piazza is the point around which the rest of the town organizes itself: shops and a market under the arcades, a rebuilt church closing its south end, and the roads out toward the castles and the hamlet all beginning at its edges. The Saturday market fills the piazza.

The wine festival in early September empties the surrounding cellars into glasses for three days. What holds the place together is the geography more than any single monument: a market town at a river crossing, ringed by the vineyard slopes and the older hill settlement that all feed into the same triangular square.

What to see in Greve in Chianti

• Piazza Matteotti. The arcades shelter wine shops, butchers and pasticcerie, wrapped around the irregular triangle of paving with the navigator's bronze figure watching the center.
• Chiesa di Santa Croce. Neoclassical parish church on the south point of the piazza, rebuilt in the nineteenth century after earthquake damage.
• Castello di Verrazzano. Vineyard estate on the hills north of town, producing Chianti Classico on slopes tied to the family name that reached New York Bay.

How to get to Greve in Chianti

Florence is about 44 min away by road.

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5. Fiesole

Best for a trip without a car. The train stops in the commune.

24 min from Florence · homes €2,250 to €3,400 a m² in the center · 13,809 people

Why visit Fiesole

Fiesole was Viesul to the Etruscans and Faesulae to the Romans, who took it in 283 BC. Florence claimed it in 1125 and never let it go, which is the reverse of the usual order: the hill town came first, the valley city second, and the ridge has watched its own successor grow across the centuries since.

The convent that crowns the highest point sits at 345 meters. Today the town functions as the hill seat of Florentine villas, the Villa Medici among them, so the relationship between Fiesole and Florence is not just historical but residential: those with means built upward, toward the older settlement, to look down on the newer one.

What to see in Fiesole

• Teatro Romano. Stone tiers set into the hillside below the cathedral, still used each summer for the Estate Fiesolana, so the seats fill for performances the way they once did in antiquity.
• Cattedrale di San Romolo. Romanesque cathedral founded in 1028, flanked by a 42-meter bell tower, with a marble altar from 1273 and two Pietro Perugino frescoes.
• Convento di San Francesco. Romanesque-Gothic Franciscan convent at the ridge's highest point, 345 meters, with cloisters and a panoramic view back over Florence.

How to get to Fiesole

It has its own railway station. Florence is about 24 min away by road. The full route from Florence.

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6. Vinci

Best for a wine weekend. It belongs to the national association of wine towns.

41 min from Prato · homes €1,100 to €1,650 a m² in the center · 14,587 people

Why visit Vinci

Vinci sits at 97 meters on the slopes of Montalbano, twenty-five kilometers west of Florence, its vineyards and olive groves laid out on terraces held by dry stone walls. The town takes its name from this landscape, and the massif gives the place its rhythm: the working land climbs above the rooftops, and the paths between the houses lead directly into the terraces.

The town itself is small enough that its parts read as one route. The parish church sits at the foot of the castle, low in the settlement; the farmhouse at Anchiano stands uphill, reached by a pedestrian path that crosses the same vineyards and olive terraces as the rest of Montalbano.

Vinci below, Anchiano above, joined by a walk through cultivated slopes rather than street: the geography ties birth, baptism and childhood to a single continuous stretch of ground, with the castle holding the town's other claim, the machines built from drawings made by a boy who walked this same hill.

What to see in Vinci

• Castello dei Conti Guidi. Twelfth-century elliptical castle with tall keep, called the ship castle, home of the Museo Leonardiano since 1953.
• Museo Leonardiano. One of the world's largest collections of models built from Leonardo's drawings, spread across the castle and the Palazzina Uzielli.
• Casa Natale di Leonardo (Anchiano). Stone farmhouse reached by climbing uphill from town, its rooms restored as a small museum around the tradition of the birthplace.

How to get to Vinci

Prato is about 41 min away by road.

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7. Certaldo

Best for a stage of a long walk. The Via Francigena passes through.

46 min from Florence · homes €1,100 to €2,100 a m² in the center · 15,667 people

Why visit Certaldo

Certaldo sits in the Valdelsa twenty-five kilometers southwest of Florence, with a lower town on the plain at 67 meters and the medieval Certaldo Alto on the hill above, reached by a funicular. The upper town is built almost entirely of red brick rather than the usual Tuscan stone, an unusual visual signature for the region.

Giovanni Boccaccio lived his last years here, dying in 1375 in the house on Via Boccaccio that is now the Casa Boccaccio museum and study center. He is buried in the Chiesa dei Santi Michele e Jacopo across the street.

The Palazzo Pretorio, fifteenth-century seat of the Florentine vicar, holds frescoes by Pier Francesco Fiorentino and the courtyard coats of arms of seventy-four podestà. Mercantia, the street-theater festival that fills Certaldo Alto every July, has run since 1988 and turns the brick streets into stages for European companies.

The local plate is cipolla rossa di Certaldo, a sweet red onion grown on the Valdelsa hills since the fifteenth century.

What to see in Certaldo

• Certaldo Alto. Medieval brick-built upper town on the hill above the plain, reached by funicular from the modern lower town.
• Casa Boccaccio. The house on Via Boccaccio where the poet lived his last years and died in 1375, now a museum and study center.
• Palazzo Pretorio. Fifteenth-century seat of the Florentine vicar, with frescoes by Pier Francesco Fiorentino and seventy-four podestà coats of arms in the courtyard.

How to get to Certaldo

It has its own railway station. Florence is about 46 min away by road. The full route from Florence.

Everything we know about Certaldo