Discover on our portal all the sites, places, monuments and activities not to be missed! Whether you rely on organized tours, or if you want to go on an adventure, here is a list of some monuments and sites that you absolutely cannot miss. Of course it all depends a lot on how many days you have available and by what means you will travel, but we can assure you that it will be worth it!

Let’s start by telling you that, whatever your path, if you love nature this is the ideal place for a nice ride or a walk following the ancient Via Cassia, the Francigena and the ancient dirt roads between vineyards and olive groves. Here you will find many bicycle and electric rental services, where they will offer you personalized tours.

Each village in the Val d’Orcia is special: you will feel like you are entering a fairy tale, visiting characteristic villages with medieval and Renaissance architecture. Castles, churches, fortresses and many panoramic terraces to discover, from which you can enjoy a fantastic view over the entire Val d’Orcia!

L'articolo Val d’Orcia tour proviene da Montepulciano.com.

Duration 1h40

Route length 30 km

Difference in height 500m

Difficulty easy

Among the most beautiful roads in the Val d’Orcia

Surely if you are looking for short and low difficulty itineraries we suggest itineraries such as Pienza – Montepulciano. An easy route for everyone and one of the most iconic and evocative roads of the Val d’Orcia, between wonderful farmhouses and the most photographed hills in the world. On your return you can reward yourself with a nice platter of pecorino di Pienza by visiting this beautiful Renaissance village!

This bike route is easy and really suitable for all those who want to enjoy the Tuscan landscape and enjoy a few stops in the villages.
It starts from Pienza, and along the SP 146 you reach Montepulciano after about 13 km. Here you can take a break, visit a city rich in gastronomic culture and stupendous monuments. Admire the Piazza Grande with the Town Hall and the Cathedral of Santa Maria Assunta, walk through the streets full of bars and restaurants and enjoy a nice plate of pici with a nice glass of Vino Nobile di Montepulciano, the excellent wine produced here. You can also visit Montepulciano with its splendid underground cellars. On the way back, depart from Montepulciano continuing towards Chianciano, and after about 2 km turn right in Villa Bianca towards Monticchiello. Continuing towards Monticchiello, keeping to the right also at the next turn, you will descend through the famous curves with cypresses to Monticchiello.
At the intersection, take the dirt road going straight, cross the stream then keep left along the road that reaches Pienza again.

L'articolo Bike tours in Val d’Orcia: Pienza – Montepulciano proviene da Montepulciano.com.

We also have e-bikes available, our electric bicycles with assisted pedaling to be able to consult the Val d’Orcia in all its beauty. We offer agreements for bikes, hotels and luggage transport: you pedal freely and we will be available for assistance (for example with the transport service).

L'articolo Cicloposse – Guided tour by bike proviene da Montepulciano.com.

Duration 1h40

Route length 24,6 km

Difficulty easy

Among the most beautiful roads in the Val d’Orcia

Surely if you are looking for short and low difficulty itineraries we suggest itineraries such as Pienza – Chapel of the Madonna di Vitaleta – San Quirico d’Orcia. An easy route for everyone and one of the most iconic and evocative roads of the Val d’Orcia, between wonderful farmhouses and the most photographed hills in the world. On your return you can reward yourself with a nice platter of pecorino di Pienza by visiting this wonderful village!

L'articolo Bike tours in heart of Val d’Orcia proviene da Montepulciano.com.

Duration 4h 30 minutes

Route length 50 km

High difficulty

This is a demanding itinerary for trained cyclists. A path with a great difference in height but that will pay off. The effort with breathtaking views of the typical landscape of the Val d’Orcia, between cultivated fields and medieval fortresses

The departure from the village of Castiglione d’Orcia will give you great emotions: you cannot fail to visit this imposing tower that overlooks the adjacent village of Rocca d’Orcia and stands out over the entire valley.
We want you to climb the Rocca and enjoy the view but we already warn you that the photos will not be able to do justice to such beauty: here you can enjoy a few hours of relaxation before resuming SR 2 in the direction of Radicofani, before resuming the SR 2 in the direction of Radicofani, and turn onto the SP 478, where the most difficult climb awaits you. Radicofani is in fact located at about 800 meters above sea level. Once you arrive in Radicofani, your gaze can range from Monte Amiata to Lake Bolsena and Trasimeno. Here the tower of the fortress of Radicofani dominates, historically the figure of a Tuscan Robin Hood who took refuge here in 1297.
Between the stone houses and the narrow streets, don’t forget to visit the beautiful Radicofani. But if you just want to rest, perhaps in the shade of a beautiful grove, find shelter in Bosco Isabella, a fascinating garden defined as “romantic and esoteric”.

L'articolo Bike tours in Val d’Orcia: Castiglione d’Orcia – Radicofani proviene da Montepulciano.com.

The project originates from an agreement between the Municipal Administration of Montepulciano and the Hochschule für Musik und Tanz Köln and is supported by the generous help of private sponsors who founded the Palazzo Ricci Association and guarantee its financial basis.

L'articolo Accademia Palazzo Ricci proviene da Montepulciano.com.

After several years of experience in enogastronomy and catering, Lorena together with her son, Paolo, decided to open this cosy little restaurant in Montepulciano, where you will have the possibility of tasting the genuine, delicious dishes offered by the Sienese cuisine.

The elegant restaurant, the cosy atmosphere and the simple furniture reflect the essence of our recipes: our dishes are based on simple, natural ingredients yet prepared in an elaborate, refined way.

Montepulciano is the ideal town for lovers. So why not choose l’Osteria del Conte for a romantic dinner for two?

L'articolo Osteria del Conte proviene da Montepulciano.com.

Here you will find a unique panorama, perfect to be discovered slowly, at a walking pace, enjoying every magnificent view and the nature around you. Combine healthy physical activity with the exploration of a wonderful area, and don’t forget to stop in some cellar where you can taste the wine and products of this land!
Slowly, step by step, among nature, ancient abbeys and castles, vineyards and wheat fields you can enjoy these wonderful views and walk inside a postcard.

The route that we propose today is a real must in the Val d’Orcia: you will walk among the most iconic hills of Tuscany, an iconic landscape that has become a symbol and expression of this wonderful land!

From Pienza we will stop to visit the Quercia delle Checche, the first green monument in Italy and then continue along Bagno Vignoni and San Quirico d’Orcia, before returning to the Renaissance village of Pienza.

Length 32.7 km

Duration 6h 50

Difficulty medium

L'articolo Trekking in Val d’Orcia: the most suggestive places proviene da Montepulciano.com.

L'articolo Italian Language School Il Sasso proviene da Montepulciano.com.

The Cugusi dairy offers the opportunity to taste the various cheeses of its own production and local cured meats outdoors, all accompanied by the best wines of Montepulciano and craft beer. A real picnic area has been set up in front of the dairy. Grab the basket, choose the products you want to taste and sit at one of the tables facing the suggestive scenery of Montepulciano, overlooking our pastures and the temple of San Biagio. Discover our “cugustando picnic area”, enjoy a nice picnic and outdoors under our pergola, even your four-legged friends are welcome!

L'articolo Pic – nic at Cugusi dairy proviene da Montepulciano.com.