Tuscany is divided into smaller areas called "province". The province of Siena is the second largest and arguably the most beautiful of all the Tuscan province, with a varied landscape going from the high mountain forests of the Amiata, to the rolling clay hills of the Val d'Orcia and on to the rugged forest and vineyard clad hills of the Chianti. The Siena province is a the perfect example of what springs to mind when thinking of Tuscany: a landscape characterized by terraced hills, lush valleys, meandering rivers, castles, churches, and historic buildings and villages scattered across the countryside.
Would you like to know more about how to reach Siena? Have a look at our page on How to get to Siena
North of Siena, in the Chianti region, you'll find castles and villages such as Castelnuovo Berardenga, Castellina, Gaiole, and Radda in Chianti, all offering fabulous views of the countryside from their high positions. This famous wine-making region was fiercely contested between the rival cities of Florence and Siena - you can read how they tried to resolve their dispute and how the Sienese cleverly influenced the outcome here: Why is the black rooster a symbol of the Chianti region?.
Today you can visit the many fabulous wine-making estates and taste the excellent Chianti wine, accompanied by the local sheep's mil cheese, Pecorino, and cured 'prosciutto' ham. The area also has exceptional 18th-century gardens in Arceno, Pontignano, Villa la Pagliaia, Catignano, Geggiano, as well as Sestano in Castelnuovo Berardenga.
Read more in our guide to the Chianti region
Find a villa in Chianti here
Slightly further west the historic Via Francigena, a famous pilgrimage route heading to Rome and even Jerusalem from Northern Europe, runs along the Elsa valley, dotted with churches, ancient hostels and monasteries. The constant traffic of pilgrims and merchants brought both cultural and economic vibrancy and life to the region since medieval times. I cycled along the Francigena, a few years ago, setting off from Canterbury with a list of stopping places left by Sigeric, the archbishop of Canterbury in 994. I navigated my way through France, Switzerland and then Italy following the list and finding the same stopping places mentioned over a thousand years before by an English Bishop travelling to Rome to receive the "Pallium" from the Pope that would mark his investiture as ArchBishop. It's a rewarding trip.
Along this ancient route in the Val d'Elsa you'll find San Gimignano, renowned for its numerous towers, and Monteriggioni, famous for its medieval city walls. Colle val d'Elsa, also known as the "crystal town," was the birthplace of the acclaimed architect Arnolfo di Cambio, who built the body of Florence's famous Duomo. Unable to complete the vast cupola needed to roof the church, it was left for Brunelleschi to solve a hundred years later.
Read more in our guide to the Val d'Elsa
The Merse valley lies west of Siena and is the wild side of the province; it abounds in forests, waterways, nature trails, and medieval churches and castles in Chiusdino, Monticiano, Murlo, and Sovicille. The northern side of the river Merse is part of the Alta Merse nature reserve, while the river Farma flows through the valley, meeting the Merse and Ombrone rivers and leading to the renowned thermal baths at Petriolo, renowned since the days of Pope Pius XII. Both rivers are have excellent spots to go wild swimming, you can find more details here: Wild swimming in Tuscany.
The beautiful hilltop estate of Montestigliano is also in the Merse valley - we've been renting it for forty years now and it still as popular and as beautiful as when we started. This is a sketch I made of it, imagining myself flying before drones were popular or accessible.
During medieval times, this area west of Siena was popular with religious individuals and hermits due to its tranquility, a tradition evidenced by the presence of beautiful abbeys such as the Cistercian abbey of San Galgano near Chiusdino.
South of Siena lie the internationally renowned "Crete senesi," a unique natural landscape shaped by prehistoric erosions on sand and clay. This distinct "lunar landscape" forms a striking backdrop for medieval villages like Asciano, Buonconvento, Monteroni d'Arbia, Rapolano Terme, and San Giovanni d'Asso.
Adjacent to this area is the Val d'Orcia, characterized by gentle hills and cypress trees, with the river Orcia meandering through woods and past many intriguing old towns along the medieval route of Via Cassia. Towns such as Radicofani, Castiglione, San Quirico d'Orcia, and further towards Val di Chiana, Pienza and Montepulciano, are nestled here. This region is renowned for producing the famous red wine, Brunello di Montalcino, and offers ancient thermal baths at Bagno Vignoni and Bagni San Filippo. Montepulciano offers excellent wines, and Chianciano Terme, Montepulciano, and San Casciano dei Bagni provide healing waters, making the entire Val d'Orcia a haven for well-being and gastronomic delights.
Find out more about Thermal Spas in Tuscany
Read more in our guide to the Val d'Orcia
Or browse through these Villas in Val d'Orcia
Mount Amiata (1738 meters) overlooks the Val d'Orcia in the southern part of the province, bordered by the hills of Chianciano and Chiusi and the vast plain of Maremma. This area's woods have been inhabited since Etruscan times, and it was traversed by the medieval pilgrims' route, Via Francigena. Today, the region is a popular tourist destination and renowned ski resort, offering numerous slopes and cross-country skiing tracks. A scenic ski lift connects the mountain to the valley, passing through enchanting chestnut trees and beech forests.
The town of Abbadia San Salvatore has a wonderful 9th century Longobard crypt, featured in Tarkovski's film "Nostalghia".