What to see in Sinalunga: discovering the Valdichiana

The Valdichiana and Sinalunga: history, landscape and tradition

In the heart of Tuscany, among the rolling hills separating Arezzo and Siena, lies the Valdichiana, one of the most fertile, historic and characteristic valleys in the region. Once a marshy area, it was reclaimed in the 18th century by the Grand Dukes of Tuscany, transforming it into an agricultural area of excellence, rich in villages, farmhouses and historic farms. Today, the Valdichiana is known for the beauty of its landscapes, the authenticity of its traditions and the quality of its typical products, such as Aglione garlic and the famous Chianina cattle, from which the famous Florentine steak is obtained.

Among the most representative villages of the Valdichiana is Sinalunga, nestled on a panoramic hill offering spectacular views of the valley. Its historic centre, divided into a medieval and a Renaissance part, encompasses centuries of history, art and popular devotion.

Sinalunga is not just a place to visit, but to experience slowly: with its cobbled streets, village festivals, nature trails and authentic flavours, it is an unmissable stop for those who want to discover the truest soul of Tuscany, far from the beaten tourist track but perfectly connected to the surrounding area.

Sinalunga: a village between the Middle Ages and the Renaissance

The historic centre of Sinalunga is built on a hill overlooking the Valdichiana, in a strategic position between Siena and Arezzo. Its urban structure clearly reflects the different historical phases the village has gone through. The oldest part, dating back to the early Middle Ages, has an oval shape and still retains its original layout with narrow alleys, defensive walls and picturesque views that tell a centuries-old story. The more recent part, on the other hand, dates back to the late Renaissance, when, in the second half of the 16th century, the fortress and the keep were demolished, leaving room for a new, more open and orderly urban layout.

Strolling through the streets of the village, you can breathe in an authentic atmosphere: stone buildings, bell towers, quiet squares and panoramic views of the valley. Piazza Garibaldi is the heart of the village, from which the narrow streets leading to the main points of interest branch off. Here, tradition and everyday life mix in a perfect balance between historical memory and village life.

Far from the hustle and bustle of tourist crowds, Sinalunga is the ideal place for those who want to discover a more intimate Tuscany, made up of small gestures, genuine encounters and corners steeped in history. Every corner of the village invites you to slow down, observe and listen: whether it is an architectural detail or an elderly person recounting the history of their street, Sinalunga is a village to be experienced with curiosity and at a leisurely pace.

What to see in Sinalunga: art, faith and memory

Sinalunga surprises visitors with its rich historical and artistic heritage, preserved in the heart of the old town. In Piazza Garibaldi stands the Collegiate Church of San Martino, built in 1588, which houses valuable works of art including the Madonna and Child with Saints by Sodoma. Not far away, the Church of Santa Croce houses a panel painting of the Marriage of the Virgin attributed to the school of Luca Signorelli, an important exponent of the Italian Renaissance.

Another symbolic building is the Palazzo Pretorio, built between 1337 and 1346, which overlooks Piazza IV Novembre. Its bell tower is reminiscent of the Mangia tower in Siena, while the façade features the coats of arms of the Podestà and the stone pillory used to expose criminals to public ridicule.

Sinalunga also has interesting museums, such as Le Stanze di Larth, dedicated to Etruscan civilisation, and the Fonte del Castagno, dating back to 1265, from which underground tunnels can be visited by appointment.

To complete the cultural itinerary, just outside the town centre is the charming Church of San Pietro ad Mensulas, one of the oldest in the area, built on a former Roman settlement, a symbol of the historical continuity that characterises the entire Sinalunga area.

Rural tradition among historic farms and the Chianina breed

Sinalunga is not only history and architecture: it is also a land of countryside, deeply rooted rural traditions and a farming culture that still characterises the landscape and local identity today. In fact, some of the most important historic farms in the Valdichiana are located in this area, true testimonies of a noble and productive agricultural past.

Among these, the Fattoria della Fratta stands out, documented since 1208 and now open to visitors. La Fratta is home to a herd of Chianina cattle, a gastronomic symbol of the area, from which the famous Florentine steak is made. The building preserves a fresco attributed to Sodoma and was also chosen as the location for Matteo Garrone’s film Pinocchio starring Roberto Benigni. A place where art, agriculture and hospitality come together.

Also of great interest is the Amorosa, an ancient medieval fortification converted into a farm and now a prestigious accommodation facility, and the Real Fattoria di Bettolle, evidence of the reclamation of the Valdichiana valley by the Grand Dukes of Tuscany. The latter belonged to the Knights of St. Stephen and still houses the cross of the Order set in the farm walls.

These farms not only tell a centuries-old story, but today offer hospitality, food and wine experiences, nature walks, tastings of typical products and guided tours of the farms.

Sinalunga thus represents a perfect balance between rural heritage and sustainable tourism, ideal for those who want to immerse themselves in an authentic Tuscany, made up of tradition, landscape and unmistakable flavours.

Where to stay to visit Sinalunga and the Valdichiana

Visiting a rich and varied area such as Sinalunga requires the right starting point: a place that combines tranquillity, a strategic location and authentic hospitality. The B&B Country House Poggio del Drago is the ideal choice for those who want to discover not only Sinalunga, but also all the beauty of the Valdichiana aretina e senese with the convenience of being just a few kilometres from Arezzo, Montepulciano, Lucignano, Cortona and Pienza.

Nestled in the countryside, Poggio del Drago offers guests a relaxed, intimate and familiar atmosphere, far from mass tourism but at the same time well connected to the main roads. The property is perfect for couples, families or curious travellers who want to enjoy a true Tuscan experience, made up of gentle landscapes, local products, medieval villages and food and wine tours.

After a day spent visiting museums, churches, trails and well-laid tables, there is nothing better than returning to a welcoming place where you can relax in the silence of nature. Poggio del Drago is the perfect retreat for those seeking comfort without formality, sincere hospitality and a convenient base for exploring the surrounding area.

If you are planning an itinerary to discover Sinalunga, its historic farms, its popular events and the excellence of the Valdichiana, Poggio del Drago offers you everything you need:
authenticity, location and well-being in true Tuscan style.

Poggio del Drago: your retreat in the Arezzo countryside

Located between Arezzo and Sinalunga, the B&B Country House Poggio del Drago is the perfect retreat for those seeking a break from the hustle and bustle of everyday life without sacrificing comfort. Nestled in the Tuscan countryside, the B&B offers an intimate and relaxed atmosphere, with rooms with attention to detail, a wholesome breakfast and outdoor spaces ideal for enjoying the peace and quiet of the landscape.

Thanks to its strategic location, the B&B Country House Poggio del Drago is the ideal starting point for exploring Sinalunga and the entire Valdichiana, one of the most fascinating areas of Tuscany. From here, it is easy to reach villages rich in history such as Lucignano, Montepulciano, Cortona and, of course, Sinalunga, with its historic centre, historic farms and traditional events.

Food and wine lovers can enjoy authentic experiences: visit farms breeding Chianina cattle, taste pici all’aglione (pasta with garlic sauce), take part in festivals and tastings, or cycle along rural cycle routes.
All this is possible when staying in a place surrounded by nature, where you can return in the evening to relax and rediscover silence.
Poggio del Drago is perfect for those who want to discover the real Tuscany, made up of gentle landscapes, ancient flavours and sincere hospitality, just a stone’s throw from the region’s most beautiful destinations.