The best hill towns in the province of Firenze
The province of Firenze is made of ridges, and the villages sit along the tops of them because the slopes were needed for vines and olives. The building material changes as you move: pale sandstone in the Mugello north of the city, warm brick in the Valdelsa, plastered stone the colour of dust in Chianti. Autumn is the season that pays best, when the olive harvest runs and the new oil comes out of the frantoio thick and green and peppery enough to catch the throat, served on grilled bread with nothing else. Winter mornings put fog in the valleys and leave the hill towns standing clear above it, which is the view everyone means when they talk about these hills.
This is Florence's back garden, and most people never leave Florence. The Uffizi and the Duomo absorb the days, the queues run along the via dei Calzaiuoli, and the countryside gets seen through a bus window on a single afternoon with a winery stop and a panoramic viewpoint at sunset. The famous towns further out, San Gimignano above all, take the overflow, so its towers are photographed from a car park that fills by mid-morning. None of that is a criticism of the art or the towers, which deserve the attention. It does mean the crowd concentrates in a very small number of places.
The same hills carry on in every direction past those places. The vineyards continue down the Chiantigiana, the olive terraces continue west into the Valdelsa, the chestnut woods continue north into the Mugello towards the Apennine passes. The towns on this list are the inland ones built on ground too steep to spread, which is why they stayed small: a walled upper village, a piazza, a church, a road down to the fields. Fewer people go, and the oil, the wine and the views are the same.
Of the 7 communes we have mapped in the province of Firenze, 7 qualify as hill towns: each is an inland hill settlement built on ground too steep to spread. The smallest, Montaione, has 3,492 residents.
If you are still choosing, we have also written The best hill towns within an hour of Florence and The best hidden hill towns within 90 minutes of Firenze.
Montaione
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
There is no station we could confirm here, so this one means driving. Firenze is roughly 67 minutes away by road.
Our tip
April through June and September into October are the months Montaione shows best, the Valdelsa light low on the wooded ridges and the San Vivaldo chapels in their full October ochre. The Mostra del Tartufo Bianco runs the last weekend of October and the first of November. July and August push past thirty in the valley but the centro storico at 341 meters stays manageable.
Cerreto Guidi
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
There is no station we could confirm here, so this one means driving. Firenze is roughly 50 minutes away by road.
Our tip
April through June is the easiest time to walk the village and the villa garden, with the Padule di Fucecchio at its greenest. September and October dry the marsh, the harvest in the surrounding Chianti Montalbano vineyards runs through late September. July and August are hot in the lower Arno plain and the villa is the cool place to be; visitor numbers peak around mid-August. Palio del Cerro falls in September.
Barberino di Mugello
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 fourteenth-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
There is no station we could confirm here, so this one means driving. Prato is roughly 33 minutes away by road.
Our tip
April through June brings the Mugello hills into clear green and the lake of Bilancino into its season for windsurfing and small-boat sailing. September and October are dry and gold, the harvest in the upper Sieve and the chestnut woods on the higher ridges. July and August are hot enough in the valley to drive most weekenders to the lake; the two Medici villas are cool inside year-round.
Greve in Chianti
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
There is no station we could confirm here, so this one means driving. Firenze is roughly 44 minutes away by road.
✷ We have written about Greve in Chianti
“The wine is the whole economy of these hills, every village with its own, the region’s name stamped on the most famous red in Italy. Tuscan food runs to cured and roasted meat, so the wine ran red to meet it, lighter than you expect, almost fruity, easy, made to sit beside a steak and not to be lectured about. Here is the only wine knowledge you need on this road: it is all good.”
Read our piece on Greve in Chianti →Road to Siena | The Long Way Is the Better Way
Our tip
April through June and September into October are the months when the Chianti hills are at their best, green or gold depending on the harvest. July and August push past thirty degrees and the piazza empties between two and five. The wine harvest runs late September and the cellars open in turns. Expo Chianti Classico falls in September.
Fiesole
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, at 345 meters, sits at the same height Boccaccio gave the brigata in the Decameron's frame story, a detail that ties the summit to the plague-fleeing storytellers rather than to any building fact already given. 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.
The panorama from the piazza is the view that supplies the standard image of Florence from above, which means the town that Rome conquered has ended up owning the picture of the city that conquered it back.
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
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Firenze is roughly 24 minutes away by road.
Our tip
April through June and September through October are the months Fiesole was built for: the air cooler than Florence by three to five degrees, the cypress alleys clean of haze, and the Roman theatre season runs through July and early August with concerts under the open sky. July and August push the day temperature high enough that even the hilltop feels heavy at midday, though the evenings come back. November through March is quiet, light hits the cathedral late and low, and the wood-burning trattorias around Piazza Mino do their best work.
Vinci
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
There is no station we could confirm here, so this one means driving. Prato is roughly 42 minutes away by road.
Our tip
April through June brings the Montalbano hills into clear light and the Strada Verde to Anchiano fills with weekend walkers. September and October are the harvest months, vendemmia followed by olive picking. July and August are hot enough to push visitors into the cool of the castle and museum; the open-air paths empty by midday.
Certaldo
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
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Firenze is roughly 46 minutes away by road.
Our tip
April through June brings the Valdelsa hills green and the lower temperatures bearable. Mercantia runs five nights in mid-July, and the upper town becomes a single open-air theater between dusk and one in the morning. September and October are the second window, with the new oil from the surrounding hills and the start of the cipolla rossa season. Boccaccesca falls in October.
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