The best wine towns with a food festival in Toscana

San Casciano dei Bagni

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 re-enactment here is Palio di San Cassiano di San Casciano dei Bagni, usually held in August.

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

There is no station we could confirm here, so this one means driving. Perugia is roughly 68 minutes away by road.

Everything we know about San Casciano dei Bagni

Cetona

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.

The re-enactment here is Corsa delle brocche a Cetona, usually held in July.

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

There is no station we could confirm here, so this one means driving. Perugia is roughly 78 minutes away by road.

Everything we know about Cetona

Chiusi

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.

The re-enactment here is Tria Turris Medioevo e Palio delle Torri di Chiusi, usually held in June.

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

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Perugia is roughly 58 minutes away by road.

Everything we know about Chiusi

Montalcino

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 carries seven institutional signals at once, more than any other commune in this batch.

The re-enactment here is Torneo di Apertura delle Cacce a Montalcino, usually held in August.

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

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Perugia is roughly 105 minutes away by road.

Everything we know about Montalcino

Piombino

Why visit Piombino

Piombino sits on a triangular promontory pointing southeast into the Tyrrhenian, at the northern edge of the Maremma. The town was founded in the ninth century by refugees from the Etruscan port after Greek pirates attacked the city; they called the new settlement Populino, small Populonia, and the name shortened over time to what it is now.

The old city, now a frazione north on the coast, became the source of the newer town's name rather than the other way round. In the medieval period Piombino became an independent signoria under the Appiani, who ruled from here over a small state that reached out to the islands across the water.

The castle at the seafront, the piazza cantilevered out over the cliff toward Elba, and the working ferry port make up the contemporary town, each looking the same direction the refugees once looked back from: toward the older settlement to the north and the channel to the islands beyond it. The Bandiera Blu coast covers the four kilometers between the port and the old acropolis, so that the walk from new town to old runs along the same shoreline that separates them by name only.

What to see in Piombino

• Castello di Piombino. Principal defensive fortress of the city on a headland pointing southeast into the sea, with the Torrione, the Rivellino and the Cittadella complex, now a museum.
• Piazza Bovio. Long rocky breakwater extending into the sea as La Rocchetta, terraced as a piazza, with a balcony view across the channel to Elba.
• Parco Archeologico di Baratti e Populonia. Chamber tombs from the seventh to second centuries BC cut into the ground of the Gulf of Baratti, laid out for walking among the excavated structures rather than viewed from a distance.

How to get to Piombino

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Livorno is roughly 77 minutes away by road.

Everything we know about Piombino

Montepulciano

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 re-enactment here is Bravio delle Botti, usually held in August.

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

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Perugia is roughly 57 minutes away by road.

Everything we know about Montepulciano