Province of Arezzo Luxury Itinerary: The Perfect 7-Day Guide

Here is what every guidebook consistently gets wrong about the Province of Arezzo: they treat it as a supporting act. A pretty corridor between Florence and Rome. A place to pass through on the way to somewhere else, perhaps pausing to photograph the cypress-lined road at Monticchiello or pick up a bistecca in the city and move on. This is a category error of some magnitude. The province – which sprawls gloriously from the upper Arno valley through the Casentino forests, across the wild Apennine ridges and down into the wide golden bowl of the Valdichiana – is one of the most quietly extraordinary territories in all of Italy. It has Piero della Francesca, some of Tuscany’s most serious wine country, medieval towns that genuinely have not been spoiled, and a culinary tradition that cooks with the confidence of people who have never needed to impress anyone. Seven days here is barely enough. It is, however, a very fine start.

This province of Arezzo luxury itinerary is designed to move you through the region at a pace that allows things to actually sink in – mornings with intention, afternoons with some give in them, evenings that last as long as they should. Consider it a framework rather than a schedule. Italy, in general, resists over-scheduling. Arezzo, specifically, will punish it.

For full background on towns, transport and what to know before you arrive, see our Province of Arezzo Travel Guide.

Day One: Arrival and the City of Arezzo – Read the Room Before You Rush

Theme: Orientation and First Impressions

Morning: Arrive and resist the urge to immediately do anything. This sounds like indulgence but is actually strategy. Check into your villa, open the shutters, pour whatever needs pouring, and absorb the landscape for an hour. The Province of Arezzo rewards those who slow down first and plan second.

By late morning, drive into the city of Arezzo itself. Park below the old town and walk up – the gradient is part of the point. The city has a particular quality in the morning light, before the day fully organises itself: the Piazza Grande is quiet, the medieval buildings throw long shadows across the sloping square, and the Pieve di Santa Maria stands with the kind of Romanesque assurance that makes you feel mildly underdressed. Take your time here. Nobody is waiting.

Afternoon: After a lunch at one of the trattorias just off the main piazza – look for handwritten menus and paper tablecloths, both reliable indicators of seriousness – spend the early afternoon in the Basilica di San Francesco. This is where Piero della Francesca’s cycle of frescoes, The Legend of the True Cross, lives. Book ahead. The viewing is managed in timed groups, which sounds regimented but actually means you stand in front of one of the great achievements of fifteenth-century painting without someone’s selfie stick in your peripheral vision. Spend the time you have well. Piero rewards sustained looking.

Evening: Dinner in Arezzo proper. The city has a genuine restaurant culture – this is not a tourist resort making do, but a working Tuscan city that eats very well. Seek out places specialising in Chianina beef, the local breed whose steaks are grilled simply and served with nothing more complicated than olive oil and perhaps a scattering of Maldon salt. Order the bistecca. It would be rude not to.

Practical tip: Frescoes in the Basilica di San Francesco must be pre-booked. Do this before you travel, particularly in high season. The visit has a time limit; use every minute.

Day Two: The Casentino Valley – Into the Forest

Theme: Nature, Monasteries and Deep Quiet

The Casentino is the province’s best-kept secret, which is saying something in a region that is already relatively undervisited by international standards. It is a high, enclosed valley running north from Arezzo, dense with ancient forest and scattered with Romanesque churches, hermitages and villages that seem to exist at a slight remove from the twenty-first century. Not in a twee, preserved-for-tourists way. More in a genuinely-couldn’t-care-less way, which is considerably more appealing.

Morning: Drive north into the Casentino and visit the Santuario della Verna, the mountain monastery where Saint Francis received the stigmata in 1224. Whatever your theological position, the location is extraordinary – clinging to a rock face at nearly 1,300 metres, surrounded by beech forests, with views over the valley that make the drive feel wholly justified. The complex is still an active Franciscan friary, which means there is a meditative atmosphere that you do not have to manufacture. It simply exists. Walk the corridors quietly. They have been asking this of visitors for eight centuries and they are not wrong to.

Afternoon: Descend to the valley floor and visit Poppi, whose thirteenth-century castle – the Castello dei Conti Guidi – looks precisely as a medieval Tuscan castle ought to look. The views from the battlements over the valley are worth the climb up through the town. After the castle, take a slow drive along the valley roads to the Romanesque abbey of Camaldoli. The monks here have been making herbal liqueurs and skin preparations since the eleventh century. The pharmacy attached to the monastery sells them. This is the sort of souvenir that actually makes sense.

Evening: Return to your villa for dinner. If you have arranged a private chef for the week – and this is the kind of week that warrants one – the Casentino evening is the perfect occasion for something rooted in the local larder: porcini mushrooms from the forest floor, hand-rolled pasta, aged Pecorino. Eat on the terrace. The Casentino dark is very dark indeed. The stars are worth staying up for.

Day Three: Cortona and the Valdichiana – High Town, Wide Valley

Theme: Art, Altitude and Etruscan History

Cortona sits on a steep hillside above the Valdichiana with the kind of elevated confidence that comes from having been important for a very long time. The Etruscans were here before the Romans. The Romans before the medieval communes. Fra Angelico before Luca Signorelli. The town has had a lot of practice being worth visiting, and it shows.

Morning: Arrive early in Cortona before the tour groups organise themselves. The Museo Diocesano holds one of Fra Angelico’s most luminous Annunciations – a painting of such serene, light-filled delicacy that it stops most people mid-step. The museum is small and unhurried. This is a virtue. Spend time with the Signorelli paintings too; he was a local, and the work has the particular intensity of someone with something to prove.

Afternoon: Lunch at one of the restaurants on the Piazza della Repubblica, then walk the walls. Cortona’s Etruscan walls are among the oldest in Italy and loop around the upper reaches of the town with a solidity that makes later civilisations seem slightly provisional. In the afternoon, drive down to the Valdichiana floor and visit the Basilica di Santa Maria delle Grazie al Calcinaio – a Renaissance church of extraordinary geometric purity that sits in the valley below the town. Most visitors to Cortona never find it. That is their loss and your good fortune.

Evening: Dinner in Cortona. The town has several excellent restaurants and the local Valdichiana beef and truffle preparations are worth seeking. Book ahead; the better tables fill.

Day Four: Monteverchi, Terranuova and the Valdarno – Slow Wine Country

Theme: Wine, Landscape and the Art of Doing Less

The upper Valdarno – the Arno valley running south from Florence toward Arezzo – is not on most visitors’ itineraries. This is, to put it plainly, their mistake. The landscape here has a particular quality: broader and more open than the hill towns, with a scale that feels almost cinematic. Leonardo da Vinci, who grew up in this valley, used it as background in several of his paintings. You will recognise it immediately and feel, for a moment, as though you are stepping into a canvas.

Morning: Begin with a visit to the Museo Paleontologico in Montevarchi, which holds fossils of megafauna excavated from the Valdarno – giant hippos, ancient elephants, and other things that make you think differently about what this landscape used to be. It sounds academic; it is actually rather wonderful. Afterwards, drive the back roads through the vine-covered hills around the valley.

Afternoon: This is wine country. The Valdarno DOC produces wines of real character – mostly Sangiovese-based reds, with the depth that comes from well-managed altitude and good soils. Arrange a private visit to one of the area’s estate wineries. A proper guided tasting, ideally with a vertical of their best vintages and food pairings prepared in the winery kitchen, is one of those afternoons that earns its place in the memory without trying very hard.

Evening: Return to the villa and rest. Day Five begins early and covers ground. Tonight is for the terrace, a glass of whatever you brought back from the winery, and the very specific Tuscan pleasure of having nowhere to be.

Day Five: Sansepolcro and the Piero della Francesca Trail

Theme: Art Pilgrimage and Mediaeval Border Country

Sansepolcro sits in the far east of the province, close to the Umbrian border, and it is the birthplace of Piero della Francesca. The town’s Museo Civico holds his Resurrection – a fresco of such psychological force that Aldous Huxley called it the greatest painting in the world. Huxley was not given to understatement, but on this occasion he may simply have been accurate.

Morning: Drive to Sansepolcro and arrive when the museum opens. The Resurrection commands a room that has been arranged around it with appropriate reverence. The sleeping soldiers at the base of the composition are rendered with a realism that still surprises after six centuries. The risen Christ above them is not triumphant so much as inevitable. Stand with it for as long as you can. This is a painting that repays time in a way that is difficult to explain in advance but becomes entirely clear in front of it.

The town itself is lovely – a proper small Tuscan city with a market square, good food shops, and a pace of life that feels calibrated to humans rather than logistics. Walk the streets after the museum. Buy cheese. Buy salumi. The local shops are excellent and priced for locals.

Afternoon: From Sansepolcro, drive to Monterchi to see Piero’s Madonna del Parto – his tender, extraordinary depiction of a heavily pregnant Virgin Mary, housed in its own small museum. It is a startling image: intimate, human, profoundly unusual for its period. Complete the Piero triangle by returning through Arezzo in the late afternoon for a second look at the frescoes, which will read entirely differently now that you have spent the day in his company.

Evening: A quiet dinner close to the villa. You have earned it.

Day Six: Val d’Orcia Borders and the Chiana Plain – Wide Open Tuscany

Theme: Landscape, Thermal Waters and Gastronomy

The southern edge of the Province of Arezzo touches the Val d’Orcia – the UNESCO-listed landscape that has become, in recent decades, something of a Tuscan shorthand. The area around Chianciano Terme and Chiusi sits in this border territory: thermal springs, Etruscan history, and the kind of wide agricultural landscape that is deeply satisfying to drive through slowly with no particular agenda.

Morning: Begin at Chianciano Terme, whose thermal waters have been attracting visitors since Roman times. A morning at one of the town’s established thermal spa facilities – proper hydrotherapy treatments, sulphurous pools, the full Italian thermal experience – is one of those things that sounds indulgent until you are actually in it, at which point it feels entirely sensible. Book treatments in advance.

Afternoon: Drive to Chiusi and spend the afternoon with its Etruscan heritage. The Museo Nazionale Etrusco holds pieces of real quality – painted sarcophagi, fine ceramics, jewellery of unexpected delicacy – and the town’s surrounding countryside contains Etruscan tombs that can be visited with a guide from the museum. The labyrinthine tunnel system beneath the town, fed by an ancient lake, can also be toured. It is very much worth doing.

Evening: A proper dinner. The Chiana valley is Chianina territory and the beef here – from an area that has been raising this specific breed for centuries – deserves to be eaten properly. Find a restaurant with a serious grill and a good local wine list. Order accordingly. This is the evening for doing things correctly.

Day Seven: The Slow Morning, the Long Lunch and the Reluctant Farewell

Theme: Consolidation and Departure

Final days in a place like this deserve a particular kind of attention. The temptation is to cram in one more thing – one more church, one more hill town, one more frescoed room. Resist it. The Province of Arezzo has spent the week reminding you that quality and quantity are not the same argument.

Morning: Stay at the villa. Have breakfast properly – real coffee, local bread, whatever fruit the market provided yesterday. Take a walk through the landscape immediately around you. The immediate landscape is always underrated; we spend the week going places and overlook the very view from the gate. Walk for an hour without a destination. Return for more coffee.

Late Morning: One final errand: find the local market, if one is running. The weekly markets in the province’s smaller towns – Castiglion Fiorentino, Civitella in Val di Chiana, Anghiari – are where the region shops for itself. Cheese, cured meats, vegetables, the occasional inexplicable household item, elderly men examining things very seriously before putting them back. Spend an hour and take something home that will remind you of the week.

Afternoon: The long lunch. Make a reservation at one of the better restaurants in the area – book it at the start of the week, choose somewhere you have been curious about – and spend two to three hours eating and drinking with the unhurried deliberateness of someone who understands that this is not a detour from real life but part of the actual point of it. The Province of Arezzo will not let you rush this. It knows better.

Late Afternoon: Pack. Take one last look from the terrace. Wonder, briefly and sincerely, why you ever go anywhere else.

Practical Notes for the Week

A few things worth knowing before you arrive. The province is large – covering the Casentino, Valdarno, Valtiberina, Valdichiana and the city itself – so a car is not optional, it is essential. Many of the best roads are small and winding, which is not a problem so much as an experience. Drive at Italian speeds, which in the countryside means slowly.

Reservations matter more than people expect. The Basilica di San Francesco frescoes require advance booking. Good restaurants in smaller towns have limited covers and fill several days ahead in season. Wine estate visits should be arranged before you travel. The rest – the market, the walk, the long evening – can remain beautifully unscheduled.

The best months are May, June, September and October. July and August bring heat that can be genuinely formidable in the Chiana valley, though the Casentino and higher elevations stay relatively cool. Winter has its own case: the truffle markets in autumn run into November, and the landscape stripped of foliage has a particular austere beauty that photographs cannot entirely capture.

Pack layers. Bring good walking shoes. Leave more room in the bag than you think you will need. The local food shops are very persuasive.

Where to Stay: Base Yourself in a Luxury Villa

A luxury villa is not merely accommodation for a week like this – it is the structure around which everything else organises itself. The private pool on the morning you don’t want to go anywhere. The kitchen where the private chef works through things that came from the market two hours earlier. The terrace from which the landscape of the province makes its slow, inexorable case. A hotel, however good, cannot quite replicate this particular quality of having somewhere that is, for a week, unambiguously yours.

Start planning with a luxury villa in Province of Arezzo – the range spans historic farmhouses, converted estates and contemporary retreats across the province’s varied landscapes. The right villa makes the entire week cohere. Choose carefully. The rest will follow.