The best olive oil towns within 90 minutes of Firenze
The olive harvest in the hills around Firenze runs from the end of October into December, and the whole calendar of these towns bends around it. Nets go down under the trees, crates go into the back of vans, and the mills work late so the fruit is pressed within hours of coming off the branch. What comes out is olio nuovo, thick and grassy and hot at the back of the throat, best eaten on grilled unsalted Tuscan bread with nothing else on it. The landscape that produces it is silver-grey terraces, cypress lines, drystone walls and farmhouses of stone and terracotta, held together by soil poor enough to make the trees work for their living.
Most people who come for Tuscan food and wine base themselves in Firenze and go out from there, and in high season the Uffizi queue, the Ponte Vecchio and the roads towards Montepulciano absorb almost everyone. It is understandable. The city is the best introduction to the region there is, and the standard day trip out of it is genuinely good. It is also, from May to October, shared with a great many other people doing exactly the same thing on exactly the same afternoon.
The olive groves do not stop at the edge of the day-trip circuit. They carry on through the Chianti ridges, down towards the Siena clay and west into the Valdelsa, and the towns along that stretch are the ones that put their names to olive oil rather than only to wine. Each of the places here belongs to the national association of olive-oil towns, which in practice means mills you can visit, oil sold by the producer, and a harvest the town still marks. Fewer people go, and the drive from Firenze is short.
Of the 12 communes we have mapped in within 90 minutes of Firenze, 7 qualify as olive oil towns: each belongs to the national association of olive-oil towns. The smallest, Castellina in Chianti, has 2,651 residents.
Two more lists worth reading alongside this one: The best hidden hill towns within 90 minutes of Firenze and The 9 best towns with a serious restaurant that eat well 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.
La Rocca di Castelfalfi have been named by a guide.
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.
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.
Serrae Villa Fiesole, Le Lance di Fiesole have been named by a guide.
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.
Castellina in Chianti
Why visit Castellina in Chianti
Castellina in Chianti sits at 578 meters on the watershed between the Arno and Ombrone basins, fifteen kilometers northwest of Siena and thirty-five south of Florence. Its position on the historic frontier between the two republics shaped the town: it was a Sienese border fortification reinforced in the fifteenth century by Filippo Brunelleschi and Giuliano da Sangallo against firearm warfare.
The Rocca with its fifteenth-century tower dominates the centro storico and now houses the Museo Archeologico del Chianti Senese, opened in 2006. The Via delle Volte runs the length of the eastern wall: an original ancient pomerium, once open to the sky, gradually built over by private houses against the wall and now a covered arcaded passage lined with workshops and trattorie.
The Tumulo Etrusco di Montecalvario, a sixth-century BC tomb with four burial chambers carved on the cardinal axes, sits a kilometer from the centro storico. The Gallo Nero of Chianti Classico DOCG is grown on the slopes below.
Albergaccio di Castellina, Osteria di Fonterutoli, Passo dopo Passo Osteria have been named by a guide.
What to see in Castellina in Chianti
- Rocca di Castellina. Fifteenth-century fortification with imposing keep, now housing the Museo Archeologico del Chianti Senese, opened in 2006.
- Via delle Volte. Covered arcaded walkway along the eastern wall, once an open pomerium, built over by houses pressing against the fortifications and now lined with workshops.
- Tumulo di Montecalvario. Sixth-century BC Etruscan tomb a kilometer from town, with four burial chambers carved on the cardinal compass points, excavated in the early 1900s.
How to get to Castellina in Chianti
There is no station we could confirm here, so this one means driving. Firenze is roughly 63 minutes away by road.
Our tip
April through June and September into October are the working months on the Chianti watershed: vine work, harvest from mid-September, mild days at 578 meters. The Festa del Vino in the second half of September fills the centro storico for a long weekend. July and August are warmer but stay below the inland Maremma heat, and the Via delle Volte is reliably cool.
San Gimignano
Why visit San Gimignano
San Gimignano sits at 334 meters in the Val d'Elsa, halfway between Firenze and Siena on the medieval pilgrim road to Rome. Patrician families built 72 tower-houses in the twelfth and thirteenth centuries as proofs of wealth and platforms for vendettas; 14 still stand, the tallest being the Torre Grossa at 54 meters.
The town declared independence from the bishops of Volterra in 1199 and grew rich on saffron and Vernaccia, the white wine grown on the surrounding hills and praised since Dante. The Black Death of 1348 broke the boom; San Gimignano lost more than half its population and submitted to Florence.
That collapse is the reason the medieval skyline survived. UNESCO listed the historic centre in 1990 as a complete record of feudal architecture.
Roughly three million visitors come each year, more than 400 times the resident population, and the centro storico empties into the surrounding olive groves once the day-trippers leave.
Linfa, Da Pode, San Martino 26 have been named by a guide.
What to see in San Gimignano
- Torre Grossa. Fifty-four meter civic tower attached to the Palazzo Comunale, the tallest of the surviving 14, open for the climb to the panoramic terrace.
- Piazza della Cisterna. Triangular medieval square paved in brick around an octagonal well of 1287, lined by tower houses and Romanesque palaces.
- Collegiata di Santa Maria Assunta. Romanesque parish church on Piazza Duomo, walls covered by Bartolo di Fredi and Lippo Memmi frescoes of Old and New Testament scenes.
How to get to San Gimignano
There is no station we could confirm here, so this one means driving. Firenze is roughly 61 minutes away by road.
✷ We have written about San Gimignano
“We arrived in the afternoon, into the second half of the day’s crowd. Off-season meant it was groups and guides rather than a flood, but the shops were open and doing their worst, the same garbage souvenirs, the same pasta no one local would eat, and we walked through it the way you walk through a thing you have decided not to let ruin your evening. The towers stood over all of it, indifferent, which is their whole talent.”
Read our piece on San Gimignano →San Gimignano | The Town After Seven
Our tip
April through June and September into October are the months the town is worth a full day rather than three hours. The buses still come, but late afternoon empties the piazzas and lets the towers take their light. July and August push temperatures past thirty and the centro storico becomes uncomfortable between two and six, when the stone radiates heat. Fiere delle Messi di San Gimignano falls in June.
Castelnuovo Berardenga
Why visit Castelnuovo Berardenga
The commune sits east of Siena, where the hills give way to the clay swells of the Crete Senesi. The name comes from the Terra Berardinga, the area controlled in the tenth century by a Frankish nobleman named Berardo, and the borgo grew up around the castle walls the Sienese Republic raised against Florence.
The centro storico, the villa and gardens at its heart, and the surrounding zone of vineyards form one continuous pattern rather than separate parts: fortress town above, wine country falling away below it toward the clay hills. Across the wider territory, 13 castles, 70 churches and 200 farms record the medieval pattern of the Sienese contado, a scatter of small fortified points and parish churches administering land rather than one dominant center.
The place reads as a border post that outlived its military purpose and settled into agriculture and the arts, its castle now a clock tower, its noble villa now a music foundation, its walls now overlooking rows of Sangiovese.
Il Visibilio, Poggio Rosso, L'Asinello and 4 more have been named by a guide.
What to see in Castelnuovo Berardenga
- Villa Chigi Saracini. Eighteenth-century villa and Italian garden inside the centro storico, its park designed by the Sienese composer Guido Chigi Saracini, whose family foundation still runs the Accademia Musicale Chigiana in Siena.
- Torre dell'Orologio. Surviving tower of the fortress, now bearing the civic clock, the highest visible point of the centro storico.
- Chiesa dei Santi Giusto e Clemente. Eighteenth-century parish church with a neoclassical façade, built on the site of an earlier Romanesque pieve.
How to get to Castelnuovo Berardenga
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 77 minutes away by road.
✷ We have written about Castelnuovo Berardenga
“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 Castelnuovo Berardenga →Road to Siena | The Long Way Is the Better Way
Our tip
April through June and September into October are the months Chianti Classico shows best, the green hills moving toward the gold of harvest. The Sagra del Vino runs the second weekend of September. July and August push past thirty and the centro storico empties between two and six; the cellars on the surrounding hills offer cool tastings and longer rentals.
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.
Enoteca Baldi, Castello Vicchiomaggio, Officina della Bistecca and 2 more have been named by a guide.
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.
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.
Siena
Why visit Siena
Siena sits at 322 meters on three hills fifty kilometers south of Florence, with which it fought a defining rivalry through the thirteenth and fourteenth centuries. The historic center has been UNESCO World Heritage since 1995, preserved as a medieval city that worked deliberately to differ from Florentine urban planning.
Piazza del Campo, the shell-shaped square at the meeting point of the three original hills, fans out toward the Palazzo Pubblico, whose construction began in 1297. The Torre del Mangia next to it, built between 1338 and 1348, stands 87 meters tall, the exact height of the Duomo, a deliberate equality between church and state.
The Duomo itself, marble-clad in horizontal black and white bands, holds the inlaid mosaic floor that Vasari called the most beautiful ever made, and sculptures by Donatello, the Pisano family and Michelangelo. The Palio runs twice a year, on 2 July and 16 August: bareback riders representing seventeen contrade circle the Campo three times in roughly ninety seconds.
Ristorante Al Mangia, Osteria le Logge, Campo Cedro and 3 more have been named by a guide.
What to see in Siena
- Piazza del Campo. Shell-shaped medieval square at the meeting point of Siena's three hills, paved in 1349 in red brick divided into nine sectors for the Council of Nine.
- Palazzo Pubblico. Town hall begun in 1297, with the Sala dei Nove holding Lorenzetti's Allegory of Good and Bad Government from 1338-1339.
- Torre del Mangia. Brick tower built 1338-1348 next to the Palazzo Pubblico, 87 meters tall, set deliberately to match the height of the Duomo.
How to get to Siena
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 73 minutes away by road.
✷ We have written about Siena
“Before Florence was the banking capital of the known world, the bench belonged to Siena. The word itself comes from the bench, the banco, where the money changers sat, and in the twelfth century, the Sienese ran some of the largest banking houses in Europe, moving the money of popes and kings while Florence was still finding its feet.”
Read our piece on Siena →Siena | What you are really here for
Our tip
April through June and September into October are the dry months in central Tuscany: mild days, full openings at the museums, the Campo busy but not packed. The Palio runs on 2 July and 16 August: the city stops for the four days around each race, the trial races fill the piazza twice a day, and accommodation books out a year ahead. July and August are otherwise hot and crowded with day-trippers from Florence. Palio della Madonna di Provenzano falls in July.
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