Province of Arezzo Travel Guide: Where to Stay, Eat & Explore in Luxury

Most visitors to Arezzo arrive having seen it already. Not in person – through a screen. The city’s sloping medieval Piazza Grande appeared in nearly every exterior scene of Roberto Benigni’s La Vita è Bella, and if you watch carefully you’ll recognise the loggia, the fountain, the particular quality of the light. What the guidebooks tend not to mention is that this Piazza Grande also hosts one of Italy’s finest antiques fairs on the first weekend of every month, a sprawling, magnificent thing that spills across the cobbles and draws dealers from across Europe clutching their most beguiling finds. Arrive on that weekend and you’ll be picking through Venetian mirrors and Art Deco lamps while locals sip espresso and watch you do it. This is the Province of Arezzo at its most characteristic: unhurried, knowing, quietly magnificent, and almost entirely unbothered by the tourist industrial complex that has colonised so much of Tuscany.

Which raises the obvious question: who actually comes here? The answer, happily, is a rather good selection of people. Couples treating a milestone anniversary with the seriousness it deserves – the kind who want Michelin-listed restaurants and medieval hill towns rather than another Airbnb in Florence’s Oltrarno. Families who have done the city hotels and want a private pool, a garden large enough for children to actually run in, and the sort of space that means everyone can enjoy each other’s company without being on top of each other. Multi-generational groups – grandparents, adult children, small grandchildren – who need a villa with separate wings and a dining table that seats fourteen. Remote workers who have realised that a 500-year-old farmhouse with high-speed fibre connection and views across the Valdichiana is a considerably more civilised office than a WeWork in Shoreditch. And increasingly, wellness-focused travellers who have cottoned on to the fact that Tuscany’s thermal springs, forested hills and unhurried pace of life constitute an extremely effective, if rather more elegant, alternative to an actual wellness retreat. The Province of Arezzo, in short, rewards people who are prepared to look past the obvious.

Getting Here Is Easier Than You’d Think (and That’s Half the Point)

The Province of Arezzo sits in the southeastern corner of Tuscany, which sounds remote until you look at a map and realise it’s rather well positioned. Florence’s Amerigo Vespucci Airport is the natural gateway – approximately 80 kilometres northwest of Arezzo city, with transfers taking around an hour by private car. It’s a compact, manageable airport by Italian standards, which is to say the chaos is charming rather than distressing. Pisa’s Galileo Galilei Airport is a slightly longer drive at around 150 kilometres, but serves more international routes and connects well if you’re flying from northern Europe or want more flight options. Rome Fiumicino, roughly 230 kilometres south, is worth considering if you’re flying from further afield – the autostrada north through the Valdichiana is a genuinely enjoyable drive, which is not something one says about motorways often.

Arezzo city itself sits directly on the main Florence-Rome train line, making it one of the better-connected provincial capitals in inland Tuscany. Fast Trenitalia services connect to Florence in around 45 minutes and Rome in just over two hours. Once in the province, however, you will want a car. This is not a landscape built for public transport. The Valtiberina, the Casentino valley, the Valdichiana, the scattered hilltop villages of the Chiana – all of these require wheels, preferably good ones. The roads are narrow and the views will distract you. Drive accordingly.

Where to Eat in the Province of Arezzo: From Frescoed Cellars to Market Tables

Fine Dining

The Province of Arezzo doesn’t do fine dining in the showy, over-engineered way that some regions feel compelled to. What it does is serious, intelligent cooking with exceptional ingredients and a respect for tradition that never tips into stagnation. In Arezzo city, Le Chiavi d’Oro on Piazza San Francesco makes the strongest case for a long table and a longer evening. It carries Michelin selection status and two black knife-and-fork symbols – the inspectors’ mark for exemplary comfort – and the food matches the setting: thoughtfully crafted dishes built around high-quality local produce, a wine list that demonstrates someone has been paying proper attention, and service that is warm without being performative. The minimalist wood interior feels quietly confident, which is exactly the right register. This is not the restaurant you eat at to say you ate there. It’s the one you eat at because the food is genuinely exceptional.

Buca di San Francesco, on Via San Francesco, offers something different in atmosphere – an underground room of frescoed walls and wrought iron chandeliers that has been compared, not unfairly, to eating inside a small museum. The truffle pasta here has acquired something of a reputation, and the ribollita – that great ribbed blanket of a dish that anchors Tuscan winter cooking – is handled with care. The osso bucco is the kind of thing you think about on the drive home.

Where the Locals Eat

Antica Osteria l’Agania, tucked into Via Mazzini, has been feeding Arezzo’s residents for four generations and shows no signs of either stopping or modernising, both of which are points in its favour. The menu is a faithful document of the Tuscan kitchen: pici al ragù di cinghiale – thick hand-rolled spaghetti with wild boar sauce – ribollita, grilled wild boar, generous portions, zero pretension. It’s on the Michelin selection list, which the osteria seems mildly embarrassed about. They don’t take reservations, which means the queue forms early. Arrive before it does. The reward is an honest, deeply satisfying lunch that costs a fraction of what it would anywhere in northern Europe.

At Ristorante La Lancia d’Oro, the address does a lot of work – Piazza Grande, 18, in the Loggia Vasari – and yet the food doesn’t rely on the view. Traditional Aretine and Tuscan dishes, homemade pasta, a considered selection of local wines. It’s the kind of lunch that extends, entirely naturally, into the late afternoon. The wine list deserves its own paragraph but this is already getting long.

Hidden Gems Worth Seeking Out

Trattoria Il Saraceno, also on Via Mazzini, is the sort of place that could easily be walked past – it requires neither a large sign nor a man standing outside to fill it. The cooking is rooted in Aretine tradition and the atmosphere is reliably local. Neighbourhood restaurants of this quality exist across the province, though they tend not to be in the neighbourhoods visitors walk through. This is rather the point. Venture into the residential streets behind the historic centre of Arezzo and ask in any bar where the locals eat. They will tell you. Italians are generous about food.

Beyond the city, the hill towns of the province harbour trattorias attached to agriturismo estates where the olive oil was pressed last November and the pecorino comes from a farm you can see from the table. These places have neither TripAdvisor pages nor Instagram presence. They exist because they have always existed, which is the best possible qualification.

The Province Itself: A Geography Worth Understanding

The Province of Arezzo is one of those destinations that repays having a rough mental map before you arrive, because its four distinct valleys are four different experiences. The Valdichiana – the broad agricultural plain stretching south toward the Umbrian border – is where the white Chianina cattle that give Bistecca alla Fiorentina its pedigree are actually raised. Driving through it you begin to understand why the steak tastes the way it does. Cortona sits above the valley on a hill so steep and so dramatically sited that its views across to Lake Trasimeno in Umbria have been, frankly, giving people ideas about moving to Italy for centuries.

The Casentino, to the northeast of Arezzo city, is wilder, more forested, and considerably less visited. The upper Arno valley here is lined with Romanesque abbeys and medieval castles; the Foreste Casentinesi national park covers a sweep of Apennine forest so dense that it barely seems to exist in the same Tuscany as the cypress-lined postcards. Camaldoli, the eleventh-century hermitage deep in the woods, is extraordinary – monks have been keeping silence here for a thousand years, which in today’s context seems either deeply eccentric or deeply enviable.

The Valtiberina, in the east of the province, follows the upper Tiber toward Umbria and claims Sansepolcro – birthplace of Piero della Francesca – as its principal town. Small, not obviously glamorous, and home to one of the great rooms in Italian art. Then there is the Valdarno to the west, which connects the province to Florence and produces a wine, Valdarno di Sopra DOC, that remains criminally underpriced. A luxury holiday in the Province of Arezzo demands at least some time in each of these valleys. Start planning accordingly.

Things to Do That Won’t Appear in Every Best-Of List

The Piazza Grande antiques fair has already been mentioned and deserves the emphasis. On the first weekend of every month – with the main Fiera Antiquaria running since 1968 – dealers lay out centuries of accumulated Italian domestic life across the cobbles. Serious collectors come from across Europe; everyone else comes for the sport of it. Either way, leave room in your luggage.

The trail to the Eremo di Camaldoli through the Casentino forest is one of those walks that quietly rearranges your priorities. The path rises through silver fir and beech; the monastery at the top sells liqueurs and honeys made by the monks with a seriousness that suggests the afterlife question is settled and now they’re concentrating on this one. The drive up alone – through forest roads that feel implausibly remote for somewhere two hours from Florence – is worth the detour.

Cortona rewards a full day rather than the half-day most tour itineraries allocate. The MAEC – the Museo dell’Accademia Etrusca – contains an Etruscan collection of quiet astonishment, including a bronze chandelier from the fifth century BC that looks, frankly, contemporary. The town’s Sunday market fills the lower streets. Sit at a table on the main piazza with a glass of local wine around 6pm and watch the passeggiata assemble. It’s one of the better things you can do in Tuscany without spending money.

For something more structured, the thermal baths at Bagno di Romagna on the Emilia-Romagna border – just beyond the northern edge of the province – are accessible in under an hour and constitute a genuinely therapeutic afternoon. Acqua sulfurea, stone pools, the Apennines above. The experience is rather more serious and rather less Instagram-optimised than the better-known Terme di Saturnia to the south. This is not a criticism.

Adventure in the Hills: Cycling, Hiking and Riding the Valleys

The Province of Arezzo is serious cycling territory and makes no apologies for it. The roads of the Chiana valley offer long, relatively flat routes through agricultural land at its most beautiful; the Casentino presents an entirely different proposition – ascents into the Apennines on roads so quiet that you’ll hear your own breathing. Gravel cycling has taken hold here in recent years, and the network of white strade bianche that cross the province connect farm estates, hilltop villages and ancient drove roads in a way that tarmac simply doesn’t allow. The Eroica vintage cycling event, which begins nearby in Gaiole in Chianti and draws riders in period wool jerseys aboard steel-framed bicycles, has acquired something of a cult following. The sight of 8,000 people cycling heroically through the landscape while dressed as 1960s Italian club riders is either magnificent or baffling. Quite possibly both.

Hiking in the Foreste Casentinesi is among the finest walking in central Italy. The network of marked trails covers everything from gentle valley walks to serious Apennine ridge routes. The path between Camaldoli and La Verna – the Franciscan sanctuary where St Francis received the stigmata in 1224 – is a long-established pilgrim route that offers exceptional forest walking and, at La Verna itself, a cliff-edge sanctuary of concentrated spiritual drama. You don’t need to be a pilgrim to find it moving. Horse riding is well established in the province; several agriturismo estates offer access to trails through the forest and across the open hilltops. For those who prefer their adventure with a view rather than a paddle, paragliding launches from the ridges above the Casentino on days when the thermals cooperate.

The Province of Arezzo with Children: Why This Works Better Than You’d Expect

Tuscany and children have a complicated relationship in the imagination of many parents – all that irreplaceable art, all those medieval staircases, all that please don’t touch. The Province of Arezzo dissolves most of these anxieties with some efficiency. The landscape is the main event here, not fragile museum collections, and children in a private villa with a pool, a garden and a landscape to explore tend to be, in the technical sense, occupied. The agriturismo culture of the province means that many properties have working farms adjacent – animals, orchards, vegetable gardens – which add a dimension to a family holiday that no city hotel can replicate.

Families staying in one of the province’s larger luxury villas find the rhythm works naturally: mornings by the pool, afternoons in a hill town or forest, evenings cooking together in a kitchen large enough to actually function. Cortona is manageable with children – compact, walkable, with a small railway museum that performs significantly above expectations. The Casentino forest has dedicated nature trails for younger walkers. The Valdichiana farms offer occasional guided tours where children can see the Chianina cattle in their actual context rather than on a menu. All of this, combined with the kind of space and privacy that a luxury holiday in the Province of Arezzo via a private villa provides, makes the destination genuinely excellent for families who want to travel properly rather than merely survive the experience.

Art, History and the Weight of Civilisation

The Province of Arezzo has been civilised for an embarrassingly long time. The Etruscans settled the Chiana valley before Rome was a republic; Arezzo itself was a major Etruscan centre before becoming a significant Roman municipium. The MAEC in Cortona holds perhaps the finest collection of Etruscan artefacts outside of Rome and Florence, arranged in a way that rewards unhurried attention. The chimera – the bronze fire-breathing mythological creature discovered near Arezzo in the sixteenth century – is now in Florence, but the province it came from retains its character.

Piero della Francesca was born in Sansepolcro around 1415 and never really left the province spiritually. His fresco cycle The Legend of the True Cross fills the apse of the Basilica di San Francesco in Arezzo with one of the great achievements of Renaissance painting. Aldous Huxley called it the greatest painting in the world, which is the kind of thing Huxley said, but in this case the hyperbole is forgivable. Book the timed entry slot in advance. The room holds a limited number of people and the frescoes are unguarded by background noise or crowds in the way that famous art very rarely is.

Giorgio Vasari – the artist, architect and first art historian, whose Lives of the Artists effectively invented the concept of art history – was born in Arezzo in 1511. His house on Via XX Settembre, now the Casa Vasari museum, is frescoed throughout by the man himself and constitutes one of the more personal and pleasingly eccentric house museums in Tuscany. The Loggia Vasari that frames one side of Piazza Grande is his most visible architectural legacy – he designed it in the 1570s, and it has been framing the view ever since.

The Casentino’s Romanesque religious heritage is extraordinary and largely unvisited. The Abbazia di Vallombrosa, the Badia di Soffena, the Pieve di Romena – a twelfth-century Romanesque church of such purity of form that Dante apparently paused to appreciate it, which seems like a reliable endorsement – constitute a trail through medieval religious architecture that could occupy several days of genuinely absorbing travel.

Shopping: What to Bring Home and Where to Find It

The Fiera Antiquaria on Piazza Grande is the headline act – the first Sunday of each month, extending across the weekend, with around 600 dealers and an atmosphere that makes ordinary retail feel faintly inadequate. Gold jewellery, ecclesiastical textiles, Venetian glass, farmhouse ironmongery, Art Nouveau ceramics: the range is enormous and the quality genuine. Negotiating is expected. A certain scepticism about provenance is advisable. The fun, however, is consistent.

Arezzo city has a strong tradition in goldsmithing – the Oro Arezzo trade fair is one of Europe’s largest jewellery industry events, and the city’s goldsmiths have been in business since the medieval period. Several workshops and boutiques along Corso Italia and in the streets around the Duomo offer pieces that range from traditional to contemporary. This is not the place for high-street jewellery. This is the place to commission something properly made.

Local food and drink provides the most transportable souvenirs. Chestnut honey from the Casentino forests. Extra virgin olive oil from estates around Cortona. Pecorino from the hill farms of the southern province – not the mass-produced version but the aged, crumbly variety that tastes of actual grass. Wines from the Valdarno di Sopra DOC or the Cortona DOC – Syrah has been planted in the Cortona zone with results that continue to surprise people who assumed only Sangiovese was the point. The local Vin Santo, made from dried Trebbiano and Malvasia grapes, is worth seeking out specifically from estate producers rather than supermarket shelves. It bears little relationship to the generic version.

Before You Go: The Practical Details That Actually Matter

Italy uses the euro. Tipping is not mandatory in the way it is in the United States or increasingly expected as in the United Kingdom – rounding up or leaving five to ten percent in a sit-down restaurant is generous and appreciated. Rounding up the espresso at the bar is enough at a café. Italians are generally quite clear about what constitutes good behaviour at a table, and the main rule is: order properly, eat what you order, don’t ask for things that aren’t on the menu in rural Tuscany, and never put parmesan on seafood pasta. The last rule doesn’t apply here geographically but deserves repeating.

The best months to visit the Province of Arezzo are May, June, September and October. July and August are hot – genuinely, substantially hot – and while the province is less overwhelmed than the Chianti or the Cinque Terre, it is not immune to the August exodus and return of Italian domestic tourism. The countryside in May is absurdly green and flower-filled; the harvest season of late September and October, when grapes and olives are being brought in and the forests begin to turn, is perhaps the finest time of all. Winter is quiet, cold in the hills, and magical around the Christmas antiques fair. The province does not close.

Italian is the language. In the city, English is spoken in most tourist-facing contexts. In the countryside and smaller villages, a handful of Italian words – buongiorno, grazie, posso avere, per favore – will open doors that otherwise remain politely but firmly closed. Nobody expects fluency. Everyone appreciates the attempt. Safety is a non-issue in any meaningful sense. The Province of Arezzo is one of the more peaceful corners of Italy, which is itself one of the safer countries in Europe for independent travel.

Why a Luxury Villa in the Province of Arezzo Is Simply the Better Choice

There is a hotel argument for Tuscany and then there is a villa argument, and after a certain level of trip – in terms of either budget, group size, or simple ambition – the villa argument wins without much contest. The Province of Arezzo makes this particularly clear, because the landscape and the rhythm of life here are built for private habitation rather than hotel lobbies. The things that make this province extraordinary – the views across the Valdichiana, the forest mornings, the evenings with a bottle of local wine on a terrace as the light fails over the hills – are experienced most fully from a property you have to yourself.

For couples marking something significant – an anniversary, a significant birthday, a milestone that deserves more than a city minibar – a private villa with a pool and a kitchen stocked by prior arrangement with local produce is a different category of romantic gesture. For families, the space is transformative: children with a garden and a pool are infinitely more manageable than children in adjoining hotel rooms. For groups of friends, a villa with multiple bedrooms and a table that seats everyone for dinner is the difference between a good trip and a genuinely memorable one. For multi-generational travel – which is increasingly how extended families choose to holiday together, sharing a week rather than parallel but separate lives – properties with separate wings or annexes provide the rare combination of togetherness and privacy that actually works.

The remote working dimension deserves a mention. Fibre internet has reached a surprising proportion of rural Tuscany, and villa properties in the province increasingly offer reliable, fast connectivity. The combination of a proper desk, a strong signal and a view of the Apennine foothills is, empirically, a better working environment than most offices. The afternoon can then be spent cycling the strade bianche. This is a lifestyle upgrade that requires very little justification.

Wellness amenities – private pools, outdoor terraces for yoga, access to trails from the door, proximity to the thermal baths of Bagno di Romagna, the enforced deceleration that comes with living inside a landscape rather than passing through it – make a villa stay in this province an effective detox without the organised programme and the spirulina smoothies. Which, frankly, is considerably more appealing.

The province’s villa stock ranges from converted farmhouses with three bedrooms and a walled garden to grand stone casali sleeping twelve or fifteen, with staff, landscaped grounds, and wine cellars stocked from the estate’s own production. The right property here doesn’t feel like accommodation. It feels like briefly inhabiting a version of Tuscan life that happens to be very well appointed. Begin with our full collection of luxury villas in Province of Arezzo with private pool and go from there.