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Val di Chiana
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Explore Val di Chiana for Etruscan towns, Renaissance villages, vineyard roads, Chianina cuisine and the cultivated landscapes of southeastern Tuscany.

Val di Chiana is a broad, fertile valley in central Italy, extending through southeastern Tuscany between Arezzo and Chiusi, with its southern landscapes approaching the Umbrian border. It is a geographic and historic territory rather than a current administrative region, and its identity is shaped by a sequence of hill towns, vineyards, olive groves, cultivated plains and important routes linking Florence, Siena and Rome. The valley is generally experienced through its Tuscan towns, including Arezzo, Cortona, Monte San Savino, Lucignano, Sinalunga, Montepulciano and Chiusi.
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The landscape changes noticeably from north to south. Around Arezzo and Castiglion Fiorentino, the valley opens beneath wooded hills and fortified settlements; Cortona rises dramatically on the eastern slope, with wide views across the basin. Farther south, Montepulciano and the villages of the Val di Chiana Senese combine vineyards, cypress-lined roads and Renaissance architecture, while Chiusi preserves the memory of the ancient lake and marshland that once occupied much of the valley. The surrounding hills are well suited to walking, cycling and slow scenic drives, although distances between towns make planning worthwhile.
History is particularly visible here. Cortona and Chiusi were major Etruscan centres, while Roman roads and settlements connected the valley to the wider Italian peninsula. Medieval towers, churches and defensive walls mark the period when local communities competed for control of routes and farmland. Later, the Medici and the ruling authorities of the Grand Duchy of Tuscany supported extensive drainage and reclamation works, transforming marshy ground into productive agricultural land. This long relationship between engineering and cultivation remains central to the valley's appearance.
The principal towns offer different experiences. Arezzo has an urban scale, celebrated medieval art and a substantial historic centre; Cortona combines Etruscan archaeology with steep lanes and panoramic terraces; Montepulciano is known for its Renaissance palaces and Vino Nobile; and Lucignano is prized for its unusually coherent medieval plan. Sinalunga and Monte San Savino provide quieter bases for exploring the countryside, while Chiusi offers important Etruscan and Roman remains together with access to the southern end of the valley.
Food and wine are integral to the journey. Local tables draw on Tuscan traditions of bread, legumes, pasta, seasonal vegetables, olive oil and Chianina beef, the large white cattle breed associated with the valley. Wine estates range from small family producers to established cellars, particularly around Montepulciano and the southern Tuscan hills. Visitors will find the most rewarding rhythm in combining one historic town with a market, vineyard, museum or country walk rather than attempting to cover the whole valley in a single day.

When is the best time to visit Val di Chiana?

Best: May–June, September · 23–27°C
Average daytime high and rainfall by month
MonthHigh (°C)Rainfall (mm)
January880
February1070
March1475
April1880
May (best)2380
June (best)2770
July3060
August2970
September (best)2675
October2085
November1490
December985

Getting to and around Val di Chiana

How to get there

The Val di Chiana is reached most easily by rail or road. Trenitalia services connect Arezzo, Terontola-Cortona and Chiusi-Chianciano Terme with Florence, Rome and other Italian cities, although historic hill towns are usually several kilometres from their stations. The A1 motorway runs along the valley, with exits serving places including Valdichiana, Chiusi-Chianciano Terme and nearby areas. Florence Airport and Pisa International Airport are outside the valley and useful for international arrivals; Rome Fiumicino is a farther alternative for visitors approaching from the south.

Transportation

A car is the most flexible way to reach vineyards, rural churches, archaeological areas and small hill towns, but driving requires attention to restricted-traffic zones and scarce parking in historic centres. Regional buses serve some town-to-town journeys, while trains are practical along the main north-south corridor between Arezzo, Terontola and Chiusi. Taxis are more readily found at stations and in larger towns than in rural villages. Cycling is rewarding on secondary roads, though summer heat, hills and traffic on major routes should be taken into account.

Top city travel guides in Val di Chiana

The cities of Val di Chiana, and the easiest places to base yourself.

Best attractions in Val di Chiana

Val di Chiana's attractions combine Etruscan archaeology, medieval hill towns, Renaissance art and working agricultural landscapes. Cortona's archaeological museum and hillside setting introduce the valley's Etruscan heritage, while Chiusi offers underground remains, museum collections and important tombs associated with ancient Clevsin. Arezzo provides a larger urban centre with major medieval and Renaissance art, including works by Piero della Francesca. Lucignano, Monte San Savino, Sinalunga and Montepulciano reward slow exploration through lanes, churches, civic buildings and market squares. Beyond the towns, vineyards, olive groves, farm estates and quiet country roads support walking, cycling and food-and-wine visits. Some itinerary highlights are architectural rather than formal attractions: a fortified gate, a parish church or a panoramic road may reveal more about the valley than a single ticketed site. Seasonal farms and estates also provide opportunities to learn about olive oil, wine and Chianina cattle, subject to advance arrangements.

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Best landmarks in Val di Chiana

The hill towns themselves are Val di Chiana's most recognisable landmarks. Cortona's Etruscan walls and elevated position define the eastern skyline, while the fortified medieval centre of Lucignano is notable for its unusual concentric street plan and intact civic character. Montepulciano is marked by its Renaissance palaces, cathedral and Piazza Grande, arranged along a steep ridge above the southern valley. Monte San Savino preserves substantial medieval and Renaissance architecture, including its market-oriented civic spaces, while Arezzo's historic centre contains the Basilica of San Francesco, associated with Piero della Francesca's important fresco cycle. At Chiusi, the cathedral area and underground Etruscan remains express the town's long continuity from antiquity to the present. Across the valley, the open plain, wooded slopes and vineyard-covered ridges form a geographical landmark in their own right, shaped by centuries of drainage, farming and settlement.

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Explore Val di Chiana on the map

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Best restaurants in Val di Chiana

Dining in Val di Chiana is rooted in Tuscan ingredients and rural cooking rather than a single uniform menu. Chianina beef is the region's most recognisable speciality, appearing in grilled preparations and the large bistecca alla fiorentina tradition, while pici, ribollita, crostini, beans, seasonal vegetables and unsalted Tuscan bread are common across local tables. Around Montepulciano, wine is a natural accompaniment, particularly Vino Nobile and Rosso di Montepulciano, while olive-growing areas produce fragrant extra-virgin oil. Historic-town trattorie, country agriturismi, traditional inns, cafés and contemporary restaurants offer different interpretations of this food culture. Markets and farm shops are useful for pecorino, cured meats, honey, preserves and fresh produce, though individual specialities vary between communities. Reservations are sensible for popular rural dining rooms and winery meals, especially during the high season.

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Best bars in Val di Chiana

Evening life in Val di Chiana is generally social and food-led rather than centred on large nightclubs. Bars in Arezzo, Cortona, Montepulciano, Chiusi and the smaller market towns serve coffee, aperitivo and local wines, with activity often concentrated around piazzas and pedestrian streets. Historic inns, enoteche and wine bars provide opportunities to taste Tuscan wines, while restaurants and agriturismi form the main part of rural evening culture. Summer brings more outdoor dining and occasional town celebrations, but schedules vary and should be checked locally. Arezzo offers the broadest urban choice of live music and late-evening venues; elsewhere, nights are usually quieter, with conversation, a slow meal or a stroll through an illuminated historic centre taking precedence over clubbing.

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Best nightclubs in Val di Chiana

Evening life in Val di Chiana is generally social and food-led rather than centred on large nightclubs. Bars in Arezzo, Cortona, Montepulciano, Chiusi and the smaller market towns serve coffee, aperitivo and local wines, with activity often concentrated around piazzas and pedestrian streets. Historic inns, enoteche and wine bars provide opportunities to taste Tuscan wines, while restaurants and agriturismi form the main part of rural evening culture. Summer brings more outdoor dining and occasional town celebrations, but schedules vary and should be checked locally. Arezzo offers the broadest urban choice of live music and late-evening venues; elsewhere, nights are usually quieter, with conversation, a slow meal or a stroll through an illuminated historic centre taking precedence over clubbing.

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Best shops in Val di Chiana

Shopping in Val di Chiana is concentrated in historic high streets, weekly markets, food producers and independent workshops rather than large retail districts. Arezzo has the broadest urban selection, including fashion, books, antiques and specialist shops, while Cortona and Montepulciano focus on smaller galleries, ceramics, wine, olive oil, leather goods and locally inspired crafts. Market towns such as Lucignano, Sinalunga and Monte San Savino are useful for seasonal produce and everyday Italian goods, with market days varying by town. Farm shops and cantine sell Vino Nobile, extra-virgin olive oil, honey, pecorino, cured meats and preserves, although some products may be seasonal or require transport arrangements. Antiques and decorative arts have a visible place in Arezzo's retail culture, but visitors should distinguish established specialist shopping from temporary market stalls and check shipping options for bottles, ceramics or larger purchases.

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Val di Chiana essentials

Currency and Payment
Val di Chiana uses the euro, with the currency code EUR, as part of Italy. Cards and contactless payments are widely accepted in hotels, established restaurants, supermarkets, museums and wine businesses, although smaller cafés, market stalls, rural producers and some parking facilities may still be easier with cash. Carry a modest amount of euros for village purchases and transport connections, and do not assume that every unattended machine or small seasonal business accepts foreign cards.
Safety
The valley is generally straightforward for visitors, but normal precautions apply in busy historic centres, car parks and railway stations. The main practical hazards are road conditions, summer heat, steep cobbled streets and cycling or walking on roads without pavements. Use designated parking rather than entering restricted historic zones, and take care on rural roads where bends, agricultural vehicles and limited lighting are common. During hot weather, carry water on hill-town walks and check conditions before longer countryside excursions.
Emergency Situations
Italy's national emergency number is 112, which can direct callers to police, fire and ambulance services; operators may be able to assist in English, but describing the nearest town, road or landmark clearly is useful. For urgent medical problems, call 118 where available through the national emergency system or use 112. In countryside emergencies, provide a precise map location or roadside reference. The valley is not a mountain-rescue destination in the alpine sense, but outdoor callers should still give clear route details.
Do's and Don'ts
Dress respectfully when entering churches, covering shoulders and knees where requested, and keep voices low during services or visits to religious sites. Do not drive into a centro storico or ZTL unless signage confirms that access is permitted, as cameras and local regulations apply. At restaurants, service charges and tipping customs vary; rounding up or leaving a modest amount is acceptable rather than obligatory. In the countryside, stay on marked paths, close gates, avoid private farm tracks and ask before photographing people or working farms.
Local Tips
The valley floor can be considerably hotter than the hill towns in summer, so plan strenuous walks for morning or late afternoon. Station locations at Terontola-Cortona, Chiusi and Arezzo are useful transport hubs but are not themselves beside every major historic centre. Market days vary by town and season, so check locally rather than relying on a fixed assumption. A tasting appointment often provides more useful insight into Vino Nobile, olive oil or Chianina production than a brief unplanned stop at a roadside shop.
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From Eve

Local phrases worth knowing

You don't need to get them perfect. A few words go a long way, and locals appreciate the effort.

6 phrase groups · English, local and pronunciation

Basics
EnglishLocalSay it
HelloCiao[chow]
GoodbyeArrivederci[ah-ree-veh-DER-chee]
YesSì[see]
NoNo[noh]
Please/You're welcomePer favore[per fah-VOH-reh]
Thank youGrazie[GRAHT-see-eh]
Excuse me/SorryMi scusi[mee SKOO-zee]
How are you?Come stai?[KOH-meh stah-ee]
Fine. And you?Bene. E tu?[BEH-neh. eh too?]
Do you speak English?Parli inglese?[PAR-lee een-GLEH-zeh?]
I don't understandNon capisco[non kah-PEE-sko]
Eating & Drinking
EnglishLocalSay it
I'd like to see the menu, pleaseVorrei vedere il menu, per favore[vor-RAY veh-DER-eh eel meh-NEW, per fah-VOH-reh]
I don't eat meatNon mangio carne[non MAHN-jo KAR-neh]
Cheers!Salute![sah-LOO-teh]
I would like to pay, pleaseVorrei pagare, per favore[vor-RAY pah-GAH-reh, per fah-VOH-reh]
Emergencies
EnglishLocalSay it
Help!Aiuto![ah-YOO-toh]
Go away!Vattene via![VAH-teh-neh VEE-ah]
Call the Police!Chiama la polizia![KYAH-mah lah poh-lit-ZEE-ah]
Call a doctor!Chiama un dottore![KYAH-mah oon doh-TOH-reh]
I'm lostMi sono perso[mee SOH-noh PER-soh]
I'm illSono malato[SOH-noh mah-LAH-toh]
Shopping
EnglishLocalSay it
I'd like to buy...Vorrei comprare...[vor-RAY kohm-PRAH-reh...]
I'm just lookingSto solo guardando[sto SOH-loh gwahr-DAN-do]
How much is it?Quanto costa?[KWAN-toh KOH-stah?]
That's too expensiveÈ troppo costoso[eh TROH-poh koh-STOH-soh]
Can you lower the price?Puoi abbassare il prezzo?[pwoy ahb-BAH-rah-reh eel PRET-soh?]
Time & Numbers
EnglishLocalSay it
What time is it?Che ora è?[keh OH-rah eh?]
It's one o'clockÈ l'una[eh LOO-nah]
Half past (10)Dieci e mezza[DEE-eh-chee eh MEH-tzah]
MorningMattina[maht-TEE-nah]
AfternoonPomeriggio[poh-meh-REEJ-joh]
EveningSera[SEH-rah]
YesterdayIeri[YEH-ree]
TodayOggi[OHJ-ee]
TomorrowDomani[doh-MAH-nee]
1Uno[OO-noh]
2Due[DOO-eh]
3Tre[TREH]
4Quattro[KWAH-troh]
5Cinque[CHEEN-kweh]
6Sei[SAY]
7Sette[SEH-teh]
8Otto[OHT-toh]
9Nove[NOH-veh]
10Dieci[DEE-eh-chee]
Transport & Directions
EnglishLocalSay it
Where's a/the...?Dove c'è...?[DOH-veh cheh...?]
What's the address?Qual è l'indirizzo?[kwahl eh leen-dee-REET-soh?]
Can you show me (on the map)?Puoi mostrarmi (sulla mappa)?[pwoy mo-STRAR-mee (SOOL-lah MAH-pah)?]
When's the next (bus)?Quando passa il prossimo (autobus)?[KWAN-doh PAH-sah eel PROS-simo (OW-toh-boos)?]
A ticket (to ....)Un biglietto (per ....)[oon bee-LYEH-toh (per ....)]

History of Val di Chiana

Etruscan Cities of Cortona and Chiusi

The Val di Chiana was one of the important landscapes of Etruria, the civilisation that flourished in central Italy before Roman expansion. Cortona, known in antiquity as Curtun, occupied a strategic hill position, while Chiusi, ancient Clevsin, became a major political and cultural centre under the ruler Lars Porsenna in later tradition. Tombs, museum collections, sanctuaries and traces of ancient roads reveal a society connected to wider networks of trade and craftsmanship. Etruscan influence remains one of the valley's defining historical layers.

Roman Roads and the Clanis Valley

Roman control reorganised the valley within a larger system of roads, settlements and agricultural production. The Clanis River, which once drained southwards through a much wetter lowland, gave the valley its name. Roman routes connected centres such as Arezzo, Cortona and Chiusi with the principal roads of Italy, helping goods and people move between inland Etruria and Rome. Later changes to river courses and the accumulation of marshland altered the landscape, but the valley's role as a corridor endured.

Medieval Fortified Towns and Rival Powers

During the Middle Ages, the hills and routes of the Val di Chiana were contested by bishops, local lords, communes and the expanding powers of Florence and Siena. Towns such as Lucignano, Monte San Savino, Cortona and Montepulciano developed walls, gates, towers and churches that reflected both civic prosperity and military insecurity. Their elevated positions offered control over roads and farmland. The compact historic centres visible today are direct products of this period of political competition and urban consolidation.

Florentine and Medici Expansion

From the late medieval period into the Renaissance, Florence extended its influence across much of the northern and central valley. The Medici strengthened fortifications, reorganised territories and promoted agricultural improvement, while Renaissance architects and patrons reshaped town centres with palaces, churches and civic buildings. Montepulciano developed a particularly distinguished Renaissance appearance, associated with architects including Antonio da Sangallo the Elder. The period connected local communities to the artistic, political and economic ambitions of the Florentine state.

Drainage and the Reclamation of the Marshes

For centuries, the low-lying centre of the valley contained marshes and shallow water associated with the ancient Clanis system. Reclamation was gradual and involved canals, embankments, drainage works and changes to river management. Under the Grand Duchy of Tuscany, especially from the eighteenth century, these interventions became more systematic. The transformation created cultivable land, improved communications and reduced the problems associated with stagnant water. The open agricultural plain seen today is therefore a historic construction as well as a natural landscape.

Agriculture, Chianina Cattle and Wine

Modern Val di Chiana developed around mixed farming, cereals, olive growing, vineyards and livestock. The Chianina breed, named after the valley, became renowned for its size and hardiness and remains closely associated with Tuscan culinary culture. Wine production also gained increasing importance, particularly around Montepulciano, where Vino Nobile developed a long-established reputation. Agricultural change, improved transport and the gradual decline of sharecropping reshaped rural life during the nineteenth and twentieth centuries, while farming continues to give the valley much of its visual and culinary character.

Railways and the Modern Travel Corridor

The arrival of railways in the nineteenth century reinforced the Val di Chiana's historic role as a route between northern and southern Italy. Lines through Arezzo, Terontola and Chiusi linked local economies with Florence, Rome and other Tuscan centres, while roads later made the hill towns more accessible to visitors and agricultural markets. The principal railway stations remain on the valley floor rather than in many of the historic centres, a pattern that explains why short onward journeys by car, taxi or bus are often necessary.

Val di Chiana in Photos

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Evendo: Your Ultimate Travel Guide to Val di Chiana

Discover Val di Chiana with Evendo: a 100% free app-based travel guide covering attractions, landmarks, shops, bars, restaurants, hotels, tours, and experiences.

  • Detailed information on attractions, landmarks, shops, bars, nightclubs, restaurants, hotels, tours, and experiences
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Explore Val di Chiana like never before with Evendo, the ultimate free travel guide app. Plan your trip effortlessly with detailed information, local tips, and easy bookings.

  • Historical insights and travel essentials for Val di Chiana
  • Curated local tips to help you experience Val di Chiana like a local
  • User-friendly navigation through the app and the city
  • 'Near Me' feature to discover nearby attractions and amenities
  • 100% free with no in-app purchases

Welcome to Val di Chiana, a breathtaking region in Italy known for its rich history, stunning landscapes, and vibrant culture. With Evendo, your travel experience will be elevated to new heights. Our app is designed to provide you with all the information you need to make the most of your trip. From famous attractions like the medieval town of Montepulciano and the thermal baths of Chianciano Terme to landmarks such as the picturesque Piazza Grande in Arezzo, Evendo has it all covered.

Looking for the best places to eat? Discover top-rated restaurants such as La Grotta in Cortona and Osteria Acquacheta in Montepulciano. Our app offers detailed descriptions, images, local tips, and contact details for each location, making it easy for you to plan your culinary adventures. Whether you're in the mood for a cozy trattoria or a Michelin-starred dining experience, Evendo has recommendations to suit every palate.

But that's not all. Evendo also allows you to book hotels, tours, tickets, and experiences directly through the app. No more spending hours searching for what to see, do, and how to get there. Everything you need is in one place, making your trip planning seamless and stress-free. Our 'Near Me' feature helps you discover hidden gems and must-see spots around you, ensuring you never miss out on the best Val di Chiana has to offer.

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