The best hidden wine towns with a serious restaurant in the province of Siena
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The province of Siena is built out of Sangiovese and stone. Vines run in combed lines up the clay crete and stop where the oak woods begin, farmhouses are the color of the earth they stand on, and the towns above them are made of the same travertine and pietra serena as the cellars underneath. Autumn is when it all makes sense, the harvest trucks on the white roads, wood smoke, pici with garlic and oil, pigeon and wild boar, a bottle of Chianti Classico or Brunello opened at the table it was grown beside. Spring brings the artichokes and the first fava beans, and the thermal water in the southern corner of the province runs warm all year.
Most people arrive in Siena, walk the Campo, look at the Duomo, eat somewhere on the way back to the car park and drive on to Florence. The city earns the crowd, but it concentrates it: the restaurants nearest the shell-shaped piazza turn tables fast for people who will not return, and the wine list is often shorter than the one in a village half an hour south. In high summer the coach traffic on the approach roads makes an evening booking a logistical decision rather than a pleasure.
The vineyards do not stop at the city walls, and neither do the kitchens. The same hills carry on through Chianti and down into the Val di Chiana and the volcanic ground near the Umbrian border, and in the smaller towns along that line the good restaurant is often the only restaurant, run by people who buy from growers they know. Fewer travelers get this far. These are the towns where the wine association membership and a serious dining room happen to sit in the same street.
Of the 20 communes we have mapped in the province of Siena, 10 qualify as wine towns with a serious restaurant: each belongs to the national association of wine towns, and each holds a restaurant listed by the most demanding of the guides. This list is the hidden ones, 9 in all. The smallest, San Casciano dei Bagni, has 1,500 residents.
Two more lists worth reading alongside this one: The best olive oil towns with a serious restaurant within 90 minutes of Perugia and The 9 best wine towns that eat well within 90 minutes of Perugia.
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.
Daniela (MICHELIN) and Castello di Fighine (Gambero Rosso) are listed in food guides.
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 Cetona
The town sits on the western flank of a ridge at the meeting point of Toscana, Umbria and Lazio, where the mountain divides the Val d'Orcia from the Val di Chiana. The medieval comune passed between Siena, Orvieto and Perugia before falling to Siena in the late fourteenth century, and it was Cosimo I who later sold it whole to a marchese.
The fortress at the top of the grid and the square laid out below it are two halves of the same Renaissance move: a private residence replacing a garrison at the summit, a flat civic stage opened up at the base. Above the town, in the woods, the hermitage and the caves belong to a much older layer, human use of the mountain reaching back to the Mesolithic, long before any comune or marchese laid claim to it.
What the town adds up to is a settlement built in tiers: a prehistoric mountain, a contested medieval center, and a Renaissance overlay that reorganized the base of the hill without touching what stood above it.
Da Nilo is listed in the MICHELIN Guide and Gambero Rosso.
What to see in Cetona
- Piazza Garibaldi. Elliptical square at the foot of the medieval grid, flat and open where the streets above it climb steeply. The civic stage of the borgo, still the first thing that orients a visitor.
- Rocca di Cetona. Fortress at the top of the centro storico, its walls and keep still standing though the interior became a private residence rather than a garrison.
- Convento di San Francesco. Franciscan convent below the borgo, founded in 1212, with a single-nave church and a small cloister still in religious use.
How to get to Cetona
Perugia is about 1 h 18 min away by road.
Our tip
April through June and September into October are the months Cetona keeps its calmest pace, the wooded slopes of Monte Cetona green or rust depending on the half. July and August are hot in the centro storico but the mountain trails above 800 meters stay cool. The Mostra del Tartufo, dedicated to the local white truffles, runs the second weekend of November in Piazza Garibaldi.
Why visit Rapolano Terme
The comune sits at 334 meters on the eastern edge of the clay hills, twenty kilometers east of Siena. It was called simply Rapolano until 1949, when the spa industry pushed the name change, a shift that marks how thoroughly the waters came to define the place.
The thermal facilities and the quarry sit at some distance from each other within the comune: the springs rise near the centro and to its south, while the travertine beds lie in the Serre frazione three kilometers further out, a separate settlement built around the stone rather than the water. The medieval centro storico, meanwhile, holds no thermal or mineral history at all: a fortified perimeter, a Sienese-period castello on the highest point, and a parish church founded in the eleventh century, all predating the spa industry by centuries.
The clay-hill landscape spreads north and west of the comune, and draws most visitors past the spa itself. What emerges is a town built on two extractive industries, water and stone, wrapped around an older walled settlement that has little to do with either.
Osteria Il Granaio is listed in the MICHELIN Guide and Gambero Rosso.
What to see in Rapolano Terme
- Terme Antica Querciolaia. Six outdoor pools at 38 degrees, the older of the two facilities and the one tied to a general's convalescence.
- Terme San Giovanni. Thermal complex south of the centro among the clay hills of the Crete Senesi, with outdoor pools facing vineyards and olive groves.
- Cave di travertino di Serre. Active quarries in the Serre di Rapolano frazione three kilometers south, the source of the stone behind the Pienza Duomo's façade.
How to get to Rapolano Terme
It has its own railway station. Perugia is about 1 h 3 min away by road. The full route from Florence.
Our tip
Thermal towns work year-round and Rapolano is the rare Sienese commune where winter is a season. The pools at Antica Querciolaia and San Giovanni stay open through the cold months and the steam off the 38-degree water against the December clay hills is the postcard the spa industry sells. April through June and September into October are the wider best months, with the Crete Senesi at full color and the surrounding wine and olive harvests pulling traffic through the centro.
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 (MICHELIN and Gambero Rosso), Osteria di Fonterutoli (Gambero Rosso) and Passo dopo Passo Osteria (Gambero Rosso) are listed in food guides.
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
Firenze is about 1 h 3 min away by road.
✷ We have written about Castellina 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 Castellina in Chianti →Road to Siena | The Long Way Is the Better Way
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.
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.
Caffè Fiaschetteria Italiana (Locali Storici), Campo del Drago (MICHELIN and L'Espresso), La Sala dei Grappoli (MICHELIN and Gambero Rosso) and 13 more places are listed in food guides.
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.
✷ We have written about Montalcino
“When the film industry needed a picture of heaven, of the fields a dead hero walks home to, they came and shot it here, and that is the truest thing anyone has ever said about the Val d'Orcia. It is not a place. It is the afterlife as imagined by people who lived in cities. It is how the country looks to men who never spent an hour in it, dreamed up by Florentine bankers five hundred years ago and maintained, beautifully, ever since.”
Read our piece on Montalcino →Val d'Orcia | The Postcard Is Constructed
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 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 (MICHELIN and Gambero Rosso), Poggio Rosso (MICHELIN and Gambero Rosso), L'Asinello (MICHELIN and L'Espresso) and 4 more places are listed in food guides.
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.
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.
Ristorante Caffè Pasticceria Poliziano (Locali Storici), Osmosi (MICHELIN and Gambero Rosso), Le Logge del Vignola (MICHELIN) and 3 more places are listed in food guides.
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.
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 Chiusi
The hilltop stands above the Val di Chiana, the valley floor visible from the town at a height that made it defensible and gave it command of the surrounding farmland. The cathedral, the museums and the tunnel network are close enough to walk between within the old center, while the painted necropolis and the lake lie outside it, a few kilometers apart in different directions, one inland toward the tombs and the other north toward open water.
The tunnels themselves connect the upper town to what lies beneath it: built as drainage, later folded into legend by Pliny the Elder, who took them for part of a king's tomb. The cathedral's own columns, lifted from earlier Roman buildings, make the same point in stone that the tombs make in paint and the museum makes in bucchero and alabaster: this is a town built repeatedly on top of itself, each layer reusing what the last one left behind.
I Salotti (MICHELIN), Il Grillo è Buoncantore (Slow Food) and La Solita Zuppa (Slow Food and MICHELIN) are listed in food guides.
What to see in Chiusi
- Museo Nazionale Etrusco. Holds canopic urns, alabaster sarcophagi, bucchero pottery and grave goods pulled from the necropolises around the town.
- Duomo di San Secondiano. Cathedral built around 560 AD over an earlier basilica, renovated in the thirteenth century, nave and two aisles on antique marble columns from Roman buildings.
- Labirinto di Porsenna. Visited from the Museo della Cattedrale, the tunnels run beneath the streets at a scale that still reads as engineering rather than legend, whatever Pliny made of them.
How to get to Chiusi
It has its own railway station. Perugia is about 58 min away by road. The full route from Florence.
Our tip
April through June and September into October are the working months on the Val di Chiana edge: mild days, evening light over the lake, the wine and olive cycles below town. The Frittellata of San Giuseppe in mid-March and the Festa di San Mustiola in early June fill the centro storico with traditional kitchens. July and August push past thirty degrees and the basin below town holds the heat; the museums and the Labirinto stay cool.
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