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Tuscany offers a myriad opportunities ranging from art towns to beautiful natural sites. The region is speckled with historical centres and small villages that are certainly worth visiting. Here are some suggested itineraries:

San Gimignano

Nestled in the rolling Sienese countryside of the Val d’Elsa, San Gimignano is a small village enclosed in 13th century walls, perched on one of the hilltops between the Chianti area and the Val D’Orcia. In 1990, it was inscribed on the UNESCO World Heritage List as a heritage to be preserved. “A masterpiece of creative human genius, it is unique testimony to a past civilization, and as an exceptional exemplar of both architectonic complex and landscape, demonstrates significant passages in human history.” San Gimignano is much more than this, and different from a postcard-town crystallised in a distant golden age that serves as backdrop to stereotypical images of flag-wearers in tights, ladies, knights, and even public palazzos to which some battlements were added to foster imagery proper to a film set. It is a living asset, rich in history and stories to tell, the “book” of a society determined to express and assert its proud wealth also through daring town planning schemes. Discover more:


Siena is the town of the Palio horserace, the event that has marked the rhythm of the townsfolk’s lives for centuries. But there is much more to Siena. It is a perfectly preserved medieval town built on three hills around the world-renowned Piazza del Campo. The piazza isn’t just the place where the Palio is held twice a year; it is the navel of the town, the place from which streets drenched in history, craftsmanship and tradition branch off. The Town Hall and the Mangia Tower look out over Piazza del Campo, almost as if to protect it. Piazza del Duomo is not to be missed, dominated by the white and black marble facade of the Gothic cathedral, opposite which stands the Santa Maria della Scala museum-hospital that hosts international level art exhibitions throughout the year. Siena should be experienced unhurriedly, observed and savoured at a slow pace along its main road. A real gem in the heart of Tuscany. Discover more:


Velathri the Latin name for Volterra, was among the 12 most influential towns of the Etruscan confederation. Its walls are 7300 metres long and perfectly preserved. Its Etruscan origins are evident and tangible throughout the town. Of particular interest are the two access gates, Porta Diana and Porta dell’Arco, and the old Acropolis that comprises several buildings and the foundations of two ancient temples. The Roman theatre in the classical shape of an amphitheatre is a must-see. Over the years, Volterra has been a film set and the venue of different types of exhibitions. It is a small gem set into the hills of Tuscany; here it is possible to saunter through the narrow streets of the town centre, enjoy the typical cuisine and local specialities and yield to the magic of dreamy scenarios. Worthy of mention is the Volterra A.D. 1398, a yearly event held in the month of August that draws the town into the past with an exceptional festival where everything, from the coins and costumes to the historical reconstructions, projects visitors into a bygone age. Dicover more:


The “crown” of Siena is a must-see for anyone visiting the area. The familiar nickname is evocative of the shape of the walls that gently encircle the small village of medieval origin, the very same walls that had the honour to defend the village and its inhabitants from the many attempts of conquest. Indeed, this tiny village was disputed like a precious treasure between Florence and Siena for years on end, in the midst of duels, knights and heroes. Visiting Monteriggioni today means undertaking a journey into the Middle Ages, that here are surprisingly present. The mall artisan shops, the refreshment places and the walkway on the town walls are real attractions. It is difficult not to be overwhelmed by this enchanted village. Discover more:

The Valdelsa

Visiting the Valdelsa, with its sites and traditions, means taking a plunge into the past to discover the ancient civilization, the paths and the production establishments that have marked our history. Here we find Colle di Val d’Elsa, with its ancient town centre and its crystal. Since 1331, glass production, which became crystal production in the 1900s, is indeed one of the typical elements of this town. This is why over the past centuries it was referred to as the ‘Bohemia of Italy’ and is now considered the ‘Town of Crystal’. Poggibonsi and its Cassero, an imposing fortification unique in Tuscany and an extraordinary example in the process of landscape evolution and human settlement on the hills of central Tuscany. Archaeological excavations have revealed a millenary history, much more ancient than previously attested by documentary sources that mention the site for the first time around the mid-12th century. The Archeodrome is now open to visits and is a faithful reconstruction of a village dating back to the Frankish period (9th-mid-10th century), were one can admire huts, manor houses and crafting activities. Close by we find the small village of Staggia Senese and its castle, the Rocca, standing astride the Via Francigena. Like a book, it recounts five centuries of history through its stones. It is now possible to tread the walkways on the walls, visit the rooms of the tower that host art exhibitions and enjoy the courtyard and the other reception halls inside the castle. Discover more:


The Via Francigena

The long unfolding of history also runs along the Via Francigena, the road that connects the north of Europe to Rome, the eternal city. When walking along these gravel roads one feels like a pilgrim in a world that is not confined in history books. In modern Tuscany, the Via Francigena splits reality in two and leads deep into an unspoiled nature interrupted here and there by old refreshment places concealed in the countryside, in churches, abbeys and castles. Undertaking a journey or simply a walk along the Via Francigena means welcoming the philosophy of a pilgrim who travels with only the bare necessities, seeking to find his destination. Discover more:

Trekking and parks

Tuscany is ideal for walking and trekking. The numerous trails that lead to the discovery of hidden places, natural and historical marvels are complemented by a great number of parks. The landscape changes at every turn and it is possible to experience different adventures even in the same park. The most important parks include the Tuscan-Emilian Appennine National Park, also known as the park of the giants, the National Park of the Casentino Forests, the National Park of the Tuscan Archipelago National Park, the Apuan Alps Regional Nature Park and the Nature Park of the Maremma. Many trails also connect the smaller towns and villages to natural sites like the Elsa River Park in Colle Val d’Elsa and the Benestare Park in Gambassi Terme. Discover more:

Immerse yourself in the place...

The Palio race

The Palio horserace is held twice a year in Siena, in the famous Piazza del Campo. But what is it that makes this race so special and therefore so celebrated? First of all, attending the Palio is a unique and unforgettable experience, and then this event dates back to the Middle Ages and is in all respects a piece of history that lives on. Participation of the Sienese in the event is unbelievable and throughout the year life in the contrade, the town districts, is very lively and active. The contrade are, indeed, the beating heart of Siena, with their museums, dinners and songs. The 17 contrade are not just districts, being organised since centuries like independent states, with a Constituency, a Prior, a Church, and so on. In short, fully experiencing the days of the Palio (2nd July and 16th August) means gaining an insight into the spirit of a beautiful town anchored to its historical heritage. Discover more:


Festivals in Tuscany are a real moment of aggregation. Travellers who wish to discover the territory through the eyes of the locals will fully enjoy these events. Festivals are often dedicated to a particular dish or ingredient of traditional Tuscan cuisine but entertainment is never missing, with fairs, markets, music and live shows. Every corner of Tuscany has its own festival and discovering all of them is a real journey into the local culture. Discover more:

The Eroica

A bicycle race with truly special and unique connotations. Organised for the first time in 1997 following the idea of a group of cyclists, over the years this race has become a top level event. Dedicated to cycling as conceived in days gone by, the Eroica unfolds on the most beautiful gravel roads of Tuscany. Attending the event is a unique and indelible experience. Today, the Eroica covers different routes and is held in different seasons. It is increasingly becoming a point of reference for those who love clean cycling, the awesome views of beautiful Tuscany and the good food enjoyable at every stage! Discover more: