The best olive oil towns with a serious restaurant within 90 minutes of Perugia
Olive trees run in silver bands along the limestone hills either side of the Tuscan-Umbrian border, and the towns sitting above them are built from the same pale stone the terraces are walled with. The harvest comes late in autumn, when the mills work through the night and the new oil arrives at the table green, peppery and almost harsh, poured over bruschetta and bean soup while it is still cloudy. Winter here is cold and clear, with wood smoke in the lanes and pigeon, wild boar and hand-rolled pici on menus that change with what the season allows. Spring brings the harder light and the Val di Chiana below, flat and geometric, where the white cattle are raised for the beef these towns grill over vine cuttings.
Most people driving out of Perugia point at Assisi, and it earns its coach parks: the basilica, the frescoes, the hill town rising in rose stone above the plain. It absorbs day trippers by the thousand from Easter until late September, and the streets running up to the basilica are given over almost entirely to serving them. The food follows the crowd, which is to say it stops trying. An hour of the day is enough there, and then the rest of the region is still waiting.
The same hills, the same mills and the same cooking continue for an hour in every direction, and the towns in this list sit in that continuation. They are places where olive growing is a registered civic matter rather than a decorative one, and where at least one kitchen has been judged by the most demanding of the Italian guides and found to be doing something exact. Some sit above thermal water, some above Etruscan tombs, some above vineyards better known than the towns themselves. All are within a reasonable drive of Perugia, and all are quieter than the road to Assisi.
Of the 41 communes we have mapped within 90 minutes of Perugia, 9 qualify as olive oil towns with a serious restaurant: each belongs to the national association of olive-oil towns, and each holds a restaurant listed by the most demanding of the guides. The smallest, Trequanda, has 1,166 residents.
Elsewhere in the catalogue: The best hidden hill towns with a serious restaurant within 90 minutes of Perugia and The best olive oil towns with a medieval festival within 90 minutes of Perugia.
Trequanda
Why visit Trequanda
Trequanda is three villages in one comune: Trequanda itself at 453 meters, Castelmuzio, and Petroio at 486 meters, scattered across the hills southeast of Siena. The first written record dates to 1198, when the Cacciaconti of Scialenga held it as fief; in 1211 Emperor Otto IV gave them the right to collect tolls.
In 1553 the village was among the first to be annexed to the Grand Duchy of Tuscany. The Cacciaconti castle still anchors the centro storico, the Pieve dei Santi Pietro e Andrea next to it, built from 1327 in a Gothic-Romanesque mix and renovated in the Renaissance.
Petroio has produced fine ornamental terracotta since the early sixteenth century: lions and dogs and pineapples and chimney pots, the surface of half the gardens in central Tuscany. The municipality holds the Orange Flag from the Italian Touring Club and was inscribed in 2018 in the national register of historic rural landscapes.
Il Conte Matto, Fattoria del Colle have been named by a guide.
What to see in Trequanda
- Castello dei Cacciaconti. Medieval fortress at the center of Trequanda, seat of the Cacciaconti di Scialenga from the twelfth century.
- Pieve dei Santi Pietro e Andrea. Gothic-Romanesque parish church begun in 1327, expanded in the Renaissance, holding a fresco attributed to Sodoma.
- Castelmuzio. Walled hilltop frazione between Trequanda and Pienza, on the rural landscape register, the smallest of the three borghi.
How to get to Trequanda
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 70 minutes away by road.
Our tip
April through June brings the green months across the Crete Senesi, the clay hills holding their color before the summer burn. September and October are dry and gold, the olive harvest running through November in the Petroio and Castelmuzio frantoi. July and August touch thirty-six degrees and the three borghi go quiet between four and seven in the afternoon. Festa dell'Olio Novo falls in the season.
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.
Daniela, Castello di Fighine have been named by a guide.
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 roughly 68 minutes 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. Sagra del Ciaffagnone di San Casciano dei Bagni falls in June.
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.
Da Nilo, Il Tiglio di Piazza da Nilo have been named by a guide.
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 roughly 78 minutes 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. Sagra del Bico di Cetona falls in June.
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.
Ristorante Caffè Pasticceria Poliziano, Osmosi, Le Logge del Vignola and 3 more have been named by a guide.
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.
✷ 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. Calici di Stelle falls in July.
Bevagna
Why visit Bevagna
Bevagna sits on the floor of the Umbrian valley at 225 meters, where the Clitunno meets the Timia. Ancient Mevania, the name means she who stands in the middle, was a Roman mansio on the Via Flaminia, listed in the Antonine Itinerary.
A black-and-white mosaic of the 2nd century AD survives almost intact in the frigidarium of the Roman baths, twelve meters by seven, octopuses and dolphins in the center, tritons and sea-horses on the short sides. Piazza Silvestri at the heart of the centro storico holds two Romanesque churches that face each other at odd angles, San Michele Arcangelo and San Silvestro, built within years of each other in the late 12th century.
The Mercato delle Gaite each June turns the town into the year 1300 for ten days, four quarters competing on medieval trades and tavern menus, no anachronisms allowed. The Sagrantino slopes of Montefalco are nine kilometers up the road.
Serpillo, Ottavi Mare have been named by a guide.
What to see in Bevagna
- Piazza Silvestri. Twelfth-century civic square ringed by the Palazzo dei Consoli, the churches of San Silvestro and San Michele, and the fountain of 1896.
- Chiesa di San Michele Arcangelo. Romanesque collegiate church built by Binello and Rodolfo at the end of the 12th century, on the main square.
- Chiesa di San Silvestro. Romanesque parish church across the piazza, signed and dated 1195 by Binello, the same builder as San Michele.
How to get to Bevagna
Perugia is roughly 39 minutes away by road.
Our tip
April through June and September into October are the months for Bevagna. The valley fills with green, the Sagrantino vines run on the slopes above town, and the rose festival fills the gardens around the walls in May. The Mercato delle Gaite runs the second half of June and is the single most concentrated weekend on the Umbrian medieval calendar. Sagra della Lumaca falls in August.
Rapolano Terme
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 have been named by a guide.
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
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 63 minutes away by road.
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.
Montefalco
Why visit Montefalco
Montefalco sits on a hill above the Umbrian valley, its walls laid out in two concentric medieval circuits with five gates, the inner ring still complete and the outer ring added in the 14th century by the Trinci. At the top, the circular Piazza del Comune gathers four converging streets around the Palazzo Comunale, the high point from which the rest of the town falls away toward the walls and the vineyards beyond them.
The name Sagrantino belongs to the slopes right around those walls, where the grape has been traced back to the 1st century AD, and three of the largest producers, Caprai, Antonelli and Adanti, keep cellars within four kilometers of the centro storico. The harvest runs late September into October.
The fresco cycle Gozzoli painted in the apse of the former church of San Francesco is counted among his most complete surviving works, and the town's own name for itself, the railing of Umbria, describes the same eastern walls where the belvedere gathers seven hill towns into one view. Wine on the slopes, frescoes in the old church, a view of the valley from the walls: a hill town whose economy, art and setting all sit within walking distance of each other.
Camiano Piccolo, L' Alchimista, Locanda del Teatro and 2 more have been named by a guide.
What to see in Montefalco
- Museo Civico di San Francesco. Former Franciscan church holding Benozzo Gozzoli's fresco cycle, plus works of the Umbrian school, in a building that has stood as the town's museum since deconsecration.
- Piazza del Comune. Circular medieval square at the top of the hill, ringed by the Palazzo Comunale, the Oratorio di Santa Maria di Piazza and four converging streets.
- Belvedere of Umbria. Panoramic walk on the eastern walls that takes in Perugia, Assisi, Spello, Foligno, Trevi, Spoleto and Todi from a single viewpoint.
How to get to Montefalco
Perugia is roughly 54 minutes away by road.
Our tip
April through June and September into October are the months for Montefalco. The vineyards run their full work cycle, the harvest of Sagrantino starts in the last week of September, and the railing belvedere holds the long Umbrian light. Settimana Enologica in mid-September brings producers from across the territory onto Piazza del Comune. Enologica Montefalco falls in September.
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.
I Salotti, Il Grillo è Buoncantore, La Solita Zuppa have been named by a guide.
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.
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. Tria Turris Medioevo e Palio delle Torri di Chiusi falls in June.
Cortona
Why visit Cortona
Cortona stands on the southern flank of the Val di Chiana, looking across to Lake Trasimeno: a position that put it in sight of both the plain it governed and the water beyond it. The Etruscan name Curtun survives fixed in stone, and the city that carried it was built in tiers up the hillside, walls and fortress at the crown, church and convent lower down at the edges of the slope, houses and squares filling the ground between.
The bishop granted Francis of Assisi a place for retreat in 1211, and what resulted was built into a narrow valley below the town rather than within its walls, a retreat kept apart from the civic center even as it stayed within reach. Santa Margherita, the city's patron, is held on the ridge above the streets she once walked.
The painters Luca Signorelli and Pietro da Cortona were born inside the walls that still define the town's shape. Frances Mayes published her memoir in 1996, and the town has not been quiet since.
What emerges is a hill town whose Etruscan skeleton, medieval faith, and modern fame sit stacked on the same slope, each layer visible without erasing the one beneath it.
Il Falconiere, La Bucaccia, Osteria del Teatro and 4 more have been named by a guide.
What to see in Cortona
- Mura etrusche. The walls still ring the city entire, the foundation under every later layer of building, Roman and medieval alike.
- MAEC. Museum of the Etruscan Academy in Palazzo Casali, holding the bronze plaque and the lampadario di Cortona.
- Museo Diocesano. Collection in the former Chiesa del Gesù with Beato Angelico's Annunciation of 1430 and works by Luca Signorelli.
How to get to Cortona
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 45 minutes away by road.
Our tip
April through June brings green hills, cool evenings and the longest hours in the Diocesano without a queue. September and October are the dry, gold months, light coming in low across Lake Trasimeno and the olive harvest running until November. July and August are the difficult months. ChocoMoments Cortona falls in the season.
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