While most travellers flock to cities like Florence or the cypress-studded hills of the Val d’Orcia, Val di Chiana in southern Tuscany is a quiet and unexpected corner not to be missed. Located across the provinces of Siena and Arezzo, the Val di Chiana (the valley of the Chiana River) invites you to delve deeper and slow down.
From centuries-old wellness traditions to a rich culinary history, this part of Tuscany should be on your radar for many reasons. There are Renaissance hilltowns and ancient Etruscan remains, as well as some of Tuscany’s oldest thermal baths. Avid epicureans will discover the famous Chianina steak, which hails from this area, alongside celebrated wines from nearby Montepulciano. It’s also a prime location for walkers, cyclists and active travellers, ticking all the boxes for an enriching getaway. The best part? It’s a local secret, offering a truly authentic side to Tuscany beyond the main hotspots.
With a stay in one of our private villas, you’ll get to experience Tuscany from a local’s perspective. Let our private concierge organise guided wine tours or in-villa tastings, history walking tours, hot-air ballooning and much more. Read on to discover a side of Tuscany you’re yet to discover.
Etruscan Heritage and Hot Springs
Before the Greeks and the Romans, the Etruscan civilisation thrived in what is now Tuscany. This mysterious society inhabited the region and other parts of central Italy between the 7th and 2nd centuries BC before vanishing. When the Romans came along, they conquered the Etruscan cities one by one to make way for the rise of the Roman Empire.
Still, there are relics and remains that have been and continue to be excavated, including a series of bronze statues at San Casciano dei Bagni. These ancient hot springs reveal Val di Chiana’s centuries-old tradition of wellness and remain an ongoing archaeological excavation site, offering nearly a thousand years of ancient history. Nearby, the free thermal pools have sulphur-rich waters that can reach temperatures of 49°C and are said to have healing properties.
Above Val di Chiana, the hill town of Cortona is home to the Etruscan Academy Museum of the City – or MAEC, for short. Stop by to discover a vast collection of everyday objects, including a lamp from the fourth century BC. Be sure to see the Tabula Cortonesis up close, a bronze plaque inscribed with the Etruscan language. In the surrounding countryside, discover ancient burial sites and the tombs of Melone I and II.
Charming Villages and Hilltop Towns
Drive through the countryside of the Val di Chiana to find an array of charming towns and historic hamlets. Montepulciano is one of the valley’s most celebrated destinations, which is home to Vino Nobile di Montepulciano, one of Italy’s great red wines. Be sure to stop by this celebrated hill town to discover grand noble palaces and fine wine.
For more Etruscan treasures, Chiusi is home to the Museo Nazionale Etrusco and a fascinating underground city. Follow the network of tunnels and passages to discover a huge cistern that dates back to the first century BC. With its cypress trees and farmland, Cortona is roughly 90 minutes from Florence.
If you’re staying in one of our villa rentals near Val di Chiana, let our private concierge organise bespoke experiences. From food and wine tasting to guided walking tours, each experience can suit your preferences.
Scenic walking routes
The Val di Chiana has undergone centuries of drainage and land reclamation, transforming what became a marshy landscape into the current fertile countryside. Today, the lyrical landscapes of the Val di Chiana welcome walkers of all levels.
Punctuated with green hills and thermal waters, there are also many paths for cycling or even travelling on horseback. Our luxury villa rentals are ideally located for embarking on leisurely hikes through the countryside. Speak to our award-winning concierge for local tips and scenic routes through endless fields, where you’ll spot secluded farmhouses and rows of cypress trees.
Where to Stay – The Best Luxury Villas in Val di Chiana Italy
Podere Usil
Experience the best of Val di Chiana’s rich culinary heritage with a stay at Podere Usil. This charming Tuscan stone villa is primely located in the heart of the Val di Chiana countryside between Siena and Cortona. To uncover an authentically local experience of the area, our award-winning concierge can help organise guided tours of a local winery, where you’ll sample the region’s spectacular Syrah. Each experience is tailored to suit your preferences, whether you’re sipping fine wine in Montepulciano or uncovering Cortona’s Etruscan history.
Accommodates: 12
Location: In the heart of the Val di Chiana
Local tip: Podere Usil offers easy access to a lively weekly market every Thursday.
Vecchia Fattoria
Step inside this grand historical farmhouse for a taste of the Val di Chiana’s layered history and fine cuisine. Nestled in the quaint village of Bettolle, Vecchia Fattoria once belonged to the Grand Duke of Tuscany and his flourishing estate at the time. The term “fattoria” actually refers to the property’s former life as a working farm, where grapes or olives were pressed to make wine and olive oil.
Accommodates: 11
Location: Bettolle
Local tip: Bettolle is famed for its local produce, notably the prized "chianina" variety of beef, which hails from this very area.
Villa Astori
Showcasing panoramic views of the Val di Chiana hills, Villa Astori was designed with multi-generational reunions in mind. Sleeping up to 20 guests, this superb villa is set just moments from the ancient town of Chiusi. Use it as a base to explore the town’s rich Etruscan history and the surrounding hot springs.
Accommodates: 20
Location: Near Chiusi
Local tip: Visit art-filled medieval towns such as Sarteano, Montepulciano and Pienza, all within a forty-minute drive.
La Casa del Chiu’
Looking for a family-style villa near Cortona? Those seeking maximum privacy will relish in La Casa del Chiu’s secluded location in the Val di Chiana. Designed for a family getaway, the property is ideally located for exploring the quieter side of central Italy. Arezzo and Cortona are both within a 30-minute drive, while Siena is under 50 minutes away.
Accommodates: 10
Location: Near Cortona
Local Tip: Wine lovers can savour the local DOCG Chianti Colli Aretini and hikers can visit the luscious Casentino valley.
Val di Chiana Travel FAQs
01. How to get to Val di Chiana
By Car: A 60-minute drive from Florence and just 30 minutes from Siena and Arezzo, Val di Chiana is easily accessible thanks to its prime position in central Italy.
By Train: It’s just as seamless using the train, which will take you to Arezzo or Chiusi on the Florence to Rome line. From there, you will need a car to access the valley’s sweeping countryside.
02. What’s the best time of year to rent a villa in Val di Chiana?
Tuscany attracts millions or tourists a year, but Val di Chiana offers a quieter side to the region. Even in the summer months, you’ll avoid the influx of visitors that flock to the likes of Florence in search of the city’s cultural treasures.
Spring and autumn have to be our favourite seasons to visit the region. Witness the flowers blossom and the colours shift as the seasons change. Come for the Christmas festivities and hot springs in the winter months.
Contact our Villa Specialists
Val di Chiana should be on your radar for many reasons. Whether you’re visiting for the history or the hot springs, this is a corner of Tuscany that moves at a different pace. And if you’re seeking a truly authentic side to Tuscany, this is where to find it. With a stay in one of our private villas, our local concierge can organise enriching local experiences. From Villa Astori to Vecchia Fattoria, each villa in our collection has been handpicked and vetted by our team of local experts. Contact our Villa Specialists today to find out more about Val di Chiana and plan your stay.