The best wine towns worth staying overnight in Tuscany
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Tuscan wine is best understood late in the day, when the cellar doors are shut and the light goes long over the vines. These are towns built from pietra serena, travertine and warm brick, with enoteche on the main street and kitchens that cook to the wine rather than the other way round: pici with garlic, wild boar stewed slowly, pecorino with chestnut honey. Harvest runs through September and into October, and the smell of fermenting must carries through the alleys of the hill towns for weeks. In winter the same towns turn quiet and the tasting rooms have space at the counter, which is arguably the better trade.
Most people meet Tuscan wine on a day trip out of Florence. A coach leaves in the morning, calls at two estates on the Chianti road, and is back in the city for dinner, which means the vineyards are seen between eleven and four and the towns are seen from a car park. It works, and it is why the Chianti route between Florence and the Val d'Elsa is thick with traffic in high season. It also means almost nobody is in these places at seven in the evening, when they are at their best.
The vines do not stop at the edge of the day-trip radius. They keep going south through the Val d'Orcia and the Crete Senesi, east toward the Val di Chiana, and down to the Maremma where the Sangiovese gives way to coastal reds and the hot springs start. The towns gathered here all belong to the national association of wine towns, and each has a hotel a travel guide has vouched for, which is the practical part: you can drink properly at dinner and walk upstairs afterwards. Fewer people stay the night. That is the whole argument.
Of the 84 communes we have mapped in Toscana, 8 qualify as wine towns worth staying overnight: each belongs to the national association of wine towns, and each has a hotel a travel guide has vouched for. The smallest, San Casciano dei Bagni, has 1,500 residents.
Two more lists worth reading alongside this one: The best towns worth staying overnight in the province of Siena and The best hot spring towns worth staying overnight in Tuscany.
Why visit San Casciano dei Bagni
San Casciano dei Bagni sits at 582 meters at the southern edge of the province of Siena, above 42 hot springs that average 42 degrees Celsius. The baths were used continuously from Etruscan through Roman times and again from the Renaissance, when visitors came from across Europe.
In 2022, an excavation that began in 2019 at the ancient sanctuary turned up 24 bronze votive statues protected by mud, with around 6,000 coins in gold, silver and bronze. The find was the largest of its kind in fifty years; most surviving Etruscan votive material is terracotta.
The 1,500 residents live on a basalt outcrop above the Roman thermal complex, in a centro storico of stone houses and three small churches. The borgo joined the Borghi più belli network in 2014 and remains one of the smallest communes in Toscana to carry both that label and Bandiera Arancione.
The comune belongs to the national association of wine-producing towns.
What to see in San Casciano dei Bagni
- Santuario Ritrovato. Etruscan-Roman thermal sanctuary excavated since 2019, where 24 bronze votives and around 6,000 coins were recovered in 2022.
- Bagno Grande. The principal natural pool of the 42 hot springs, used from the second century BC through the Renaissance and reopened to the public.
- Collegiata di San Leonardo. Romanesque parish church in the centro storico, restored in the seventeenth century, with a baptismal font carved from local travertine.
How to get to San Casciano dei Bagni
Perugia is about 1 h 8 min away by road.
Our tip
The thermal pools make the calendar different here. Winter is the season many visitors prefer, when the 42-degree water steams against cold air and snow occasionally dusts the basalt outcrop. April through June and September into October are the most balanced months: warm hill light, the dry-stone walls of the borgo at their best, the sanctuary excavations open to guided tours.
Why visit Capalbio
Capalbio stands twelve kilometers from the Tyrrhenian coast, the last hill town before the border with Lazio. Charlemagne gave the land to the Abbey of Tre Fontane in 805; the Aldobrandeschi held it through the medieval period, the Orsini built the castle, and Cosimo I de' Medici took it in 1555.
It became an independent commune in 1960. The medieval walls and the fortress define the centro storico at the top of the hill; the surrounding territory drops from the wooded uplands of Monte Calmata down to the coastal reserve at Lago di Burano.
The sculpture park sits four kilometers south of the walls, apart from the old town rather than within it. A borgo that governed itself late, held by abbey, feudal lords and Medici in turn before its own commune, and a territory that runs in one line from hilltop stone to coastal wetland.
The comune belongs to the national association of wine-producing towns.
What to see in Capalbio
- Rocca Aldobrandesca. Medieval fortress at the top of the borgo, later expanded by the Orsini, with a square tower and battlements that overlook the Maremma.
- Mura medievali. Two concentric circles of walls enclosing the centro storico, with a walkable parapet that opens onto views toward the Argentario.
- Giardino dei Tarocchi. Sculpture park four kilometers south of the borgo, its ceramic and mirrored figures set among holm oaks.
How to get to Capalbio
It has its own railway station. Roma is about 1 h 48 min away by road. The full route from Rome.
Our tip
May through September is the season the borgo and its territory work together: the centro storico stays cool at 217 meters while the Tyrrhenian coast at Chiarone-Capalbio fills with swimmers. The Giardino dei Tarocchi runs April through October. July and August are hot inland; afternoon hours in the borgo thin out and the coast takes over.
Why visit Montalcino
Montalcino sits at 564 meters on a hill south of Siena, the centro storico ringed by walls and crowned by a pentagonal fortress built in 1361. When Florence took Siena in 1555, the Sienese exiles regrouped here and held out for almost four years; the Rocca itself never fell.
That date matters less to most visitors than 1980, when Brunello di Montalcino was named one of the first four Italian wines to receive DOCG status. The vineyards run from the town at 600 meters down to plots at 200, on stony galestro soils that ripen Sangiovese Grosso into a wine that ages for decades.
The Abbey of Sant'Antimo, ten kilometers south, is a Romanesque church first documented in 814 and tied by local legend to a vow by Charlemagne. The town also produces miele, olio, and the white truffles of the surrounding woods.
It holds seven designations at once: UNESCO (as part of the Val d'Orcia), Bandiera Arancione, Città del Vino, Città dell'Olio, Città del Miele, Città del Tartufo and the Via Francigena.
The comune belongs to the national association of wine-producing towns.
What to see in Montalcino
- Rocca di Montalcino. Pentagonal fortress built in 1361 by Sienese architects Mino Foresi and Domenico di Feo, refuge of the Sienese Republic after 1555.
- Abbazia di Sant'Antimo. Romanesque abbey ten kilometers south, first documented in 814, set among olive groves below the town with Gregorian chant still sung.
- Palazzo dei Priori. Thirteenth-century town hall on Piazza del Popolo, slender tower attached, civic seat of the medieval commune.
How to get to Montalcino
Perugia is about 1 h 45 min away by road. The full route from Florence.
Our tip
April through June and September into October are the months locals prefer. The hills are green or gold depending on the half, and the vineyards run their full work cycle. The Sagra del Tordo, a medieval archery contest between the four quarters of the town, takes place the last Sunday of October.
Why visit Manciano
Manciano sits at 444 meters on a hill in the southern Maremma grossetana, with a 360-degree view that runs from Monte Amiata north to the Tyrrhenian coast. The Aldobrandeschi held the original stronghold from the twelfth century.
Siena occupied the town between 1419 and 1455 and built the Rocca that still dominates the centro storico, a square keep with battlements on a shoe-base. After 1455 it returned to local rule and passed eventually to the Medici Grand Duchy.
The comune is large by Toscana standards and includes some of the best-known places of the southern Maremma: Saturnia, the Etruscan town built around its sulphurous hot springs, and Montemerano, a small walled borgo on the road to the Lago di Bolsena. The Albegna and Fiora valleys, which the town once served as a regional market, still meet at its foot.
Wine, olive oil and wild boar work the territory in roughly the order they sit on a Maremmano menu.
The comune belongs to the national association of wine-producing towns.
What to see in Manciano
- Rocca Aldobrandesca. Sienese fortress of 1424 on Aldobrandeschi foundations, square keep, walls with battlements and a solid shoe-base, dominating the centro storico.
- Saturnia. Etruscan town and frazione south of Manciano, with medieval walls, remains of a Roman road and the sulphurous hot springs used since antiquity.
- Montemerano. Small walled borgo east of Manciano, three concentric circles of streets and a fifteenth-century Madonna della Gattaiola in the parish church.
How to get to Manciano
Terni is about 2 h 12 min away by road.
✷ We have written about Manciano
“Everyone driving from Florence down to Rome crosses the Maremma without noticing, because there is nothing on that stretch to make them slow down. The hills give out. The cypresses stop. What opens up instead is flat open country, wheat and grass running off to a few low rises, the least Tuscan-looking part of Tuscany, a landscape you would call dull if you were being honest and which most guidebooks solve by leaving out.”
Read our piece on Manciano →Maremma | The Last Cowboys of Tuscany
Our tip
April through June and September into October are the months Manciano shows the southern Maremma at its best, the territory dry but green, the Saturnia pools warm against cool mornings. The Sagra dell'Anatra runs in mid-August. July and August are hot at 444 meters but easier than the coast; afternoons in the centro storico empty between two and six.
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 center 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.
The comune belongs to the national association of wine-producing towns.
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
Firenze is about 1 h 1 min 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.
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.
The comune belongs to the national association of wine-producing towns.
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
Firenze is about 1 h 17 min away by road. The full route from Florence.
✷ 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.
Why visit Montepulciano
The ridge runs between the Val di Chiana and the Val d'Orcia, 70 kilometers southeast of Siena, and the town follows its spine uphill: streets climb from the gates toward the high point, where the main square sits ringed by the buildings that define the skyline from below. The origin predates the Renaissance fabric by centuries.
Etruscan tombs survive in the surrounding hills, though almost nothing of that period shows in the centro storico itself, which was rebuilt wholesale in the fifteenth and sixteenth centuries over whatever came before. The wine and the festival both use the climb as their setting rather than their subject: the cellars are cut into the rock beneath the palazzi, keeping a constant temperature for aging, and the barrel race each August sends two men from each of the eight contrade hauling an eighty-kilogram cask up the same gradient that every visitor covers on foot, only slower.
The steepness that shaped the defensive site nine centuries ago is still what a person feels first, in the legs, before the buildings register at all.
The comune belongs to the national association of wine-producing towns.
What to see in Montepulciano
- Tempio di San Biagio. A 13-meter dome and travertine façade standing alone outside the walls, the ground falling away below it so the building reads as a single volume against the hillside.
- Piazza Grande. The high piazza at the top of the ridge, ringed by the Duomo, the Palazzo Comunale and the Palazzo Tarugi, all rebuilt in the fifteenth and sixteenth centuries.
- Palazzo Comunale. Town hall designed by Michelozzo in the fifteenth century, its tower offering a view over the Val di Chiana and Val d'Orcia.
How to get to Montepulciano
It has its own railway station. Perugia is about 57 min away by road. The full route from Florence.
✷ We have written about Montepulciano
“Now, the postcard itself, the towns, and here I have less to say than you would expect, because Pienza and Montepulciano have become, and I mean this precisely, the canteens of a theme park. They are where you go to park, walk a pretty street, use the toilet, refill the water, eat a plate of something, and buy a thing to take home. They are the food court between the rides.”
Read our piece on Montepulciano →Val d'Orcia | The Postcard Is Constructed
Our tip
April through June and September into October are the working months on the ridge: vine work in the surrounding hills, mild days, evening light that lingers over the Val d'Orcia. July and August push into the low thirties and the climb to Piazza Grande slows even the residents. The Bravìo delle Botti runs the last Sunday of August and fills the town.
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.
The comune belongs to the national association of wine-producing towns.
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
It has its own railway station. Firenze is about 1 h 13 min away by road. The full route from Florence.
✷ 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.
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