Dear Traveller friends,

after exploring the area of Chianti, now it’s time to discover another beautiful part of Tuscany—the Orcia Valley.

This area owes its well-deserved fame to the gorgeous landscapes, to the quaint little towns, and to the renowned wines. It’s no coincidence that the Orcia Valley is part of the UNESCO World Heritage and that images associated with Tuscany are often pictures of the Orcia Valley.

Introduction

Visiting the Orcia Valley requires more than just one day. The itinerary is about 200 km, the road is characterized by ups-and-downs and bends, and there are several stops worth your time along the way in this valley. That’s why I suggest a two days tour. If you have plenty of time, you can add one extra night, so that you can devote two and a half days to the Orcia Valley.

Our first day starts from Monteriggioni and arrives at Montepulciano, while during the second day you go back following another route to Siena.

Along the way, you’re going to visit the following places:

Day 1

• Buonconvento
• Montalcino
• Castelnuovo dell’Abate (Sant’Antimo Abbey)
• Castiglione d’Orcia
• Bagno Vignoni
• Montepulciano

Day 2

• Monticchiello
• Pienza
• Chapel of the Virgin Mary of Vitaleta
• San Quirico d’Orcia

Day 1

As I already said, the first day starts in Monteriggioni, which is the final stop of your tour of Chianti [LINK]. The itinerary ends in Montepulciano, the farthest town from our final destination—Siena.

Buonconvento

Your initial stop is the village of Buonconvento, more or less 45 km from Monteriggioni. It’s part of the Crete Senesi area, the access to the Orcia Valley.

Buonconvento is a small medieval village built on a plane. It’s entirely surrounded by ramparts erected around 1300. A stroll of 20-30 minutes is what it takes to visit this small village. Despite the quickness of the visit, I assure you you’re going to find the stroll pleasant and relaxing.

Montalcino

A few kilometres beyond Buonconvento, you’ll start the ascent leading to Montalcino, one of the most prominent locations in the Orcia Valley. The reason for its importance is mainly the production of the renowned wine—the Brunello di Montalcino. This wine is known all around the world, and here you can find it almost in every store.

Montalcino dates back in ancient times. It’s assumed that the first settlements were Etruscan. The development of the town, however, only happened during the Middle Ages, mainly due to its position near the Francigena Way. Moreover, for centuries, Montalcino was a centre of excellence for the production of leather. For a long time, wine production had only secondary importance. However, in 1950 a handful of producers understood the potentiality of this land and gave birth to the Brunello di Montalcino.

Visiting Montalcino isn’t that easy. Most of the streets are quite steep; thus, it can be challenging for people with mobility difficulty. The city centre, characterized by narrow and crowded alleys, is off-limits to cars. The best place to park your vehicle is the small parking lot near the Fortress, or near the hairpin turn from which you get access to Via Soccorso Saloni.

The most imposing building in town is the Fortress, overlooking the surrounding valley. Inside the ramparts, there’s nothing of particular interest, unless you want to climb over the walls to admire the view. 

After a quick tour of the Fortress, take a tour of the city centre. Don’t forget to walk through Piazza del Popolo, the heart of Montalcino. In this square, you can see the most important building in town—the Palazzo dei Priori. The Palace’s most impressive features are the emblems and crest on the facade, representing the families who ruled over the city over the centuries, and the tall tower. Part of the lower floor of the Palace is characterized by a loggia where you can often find stalls selling local products.

Castelnuovo dell’Abate

Not far from Montalcino you can find the small village called Castelnuovo dell’Abate. Your destination, however, isn’t in town. What attracts thousands of tourists each year is a short distance from the centre— Sant’Antimo Abbey.

The history of this Abbey starts in the year 350. A small oratory dedicated to the cult of the relics of Sant’Antimo from Arezzo was built on the site. During the centuries and until 1200, the Abbey was fully developed from the original oratory. The development included the building of the monastery and the church. Its influence wasn’t merely spiritual; in fact, it held a strong political dominion over the surrounding land and was supported by the Carolingian (descendants of Charlemagne). 

During the following two centuries, the Abbey was emptied of its goods and stripped of its functions. This was due to the rivalry with Siena and the influence of Pope Pius II Piccolomini. The Pope wanted Pienza, his birth town, to gain more importance. Thus, the Abbey had to lose its weight.

Only in 1870, thanks to many restoration works, the Abbey went back to its ancient splendour. After forty years of alternating religious orders, the Abbey is now in the hands of Olivetan Benedectine Fathers. Next to the monastery, you can visit a small shop that sells product made by the Fathers.

Of the entire complex, which can be visited only in part, the most beautiful part is the church. It’s quite austere, due to its Romanesque style, but it also holds some intriguing elements, such as the decorated capitals, each with a different motif.

You can visit part of the complex on your own, but some rooms are accessible only through the accompanied tour with an audioguide. The guided tour will give you access to the upper rooms connected to the church. The audioguide is full of information about the whole complex and will allow you to notice details that you may overlook otherwise.

Some well-known travel books and guides mark this visit as unmissable. However, even a quick tour on your own can suffice to understand the charm of the place. Paying the price of the ticket, however, can be a way to support the maintenance of the complex.

Before leaving, take a stroll in the field around the Abbey and admire the exterior of the bell tower.

Castiglione d’Orcia

Once you finish the tour of the Abbey, jump back in your car and head towards Castiglione d’ Orcia. It isn’t far (15 km more or less), but the road is quite tricky, and it takes half an hour to get there.

This village offers two different attraction: the ancient hamlet and the Rocca di Tentennano. Since the program for the day is quite crowded, we decided to skip the visit to the village and devote more time to the Rocca.

If you decide to visit the hamlet, the most famous attractions are the Church of Santa Maria Maddalena and the Church of Santi Stefano e Degna.

An interesting stop, especially on good weather, is the Rocca di Tentennano. This fortress, built on top of a rocky spur, for centuries had been an essential point of control over the Francigena Way. Now it’s an exceptional panoramic viewpoint that offers a 360 degrees view over the Orcia Valley and Castiglione d’Orcia.

Bagno Vignoni

The second to last stop of your first day in the Orcia Valley is Bagno Vignoni, a tiny village renowned for its thermal baths. Visiting Bagno Vignoni is as quick as a half an hour stroll. Take a walk around the famous pool in the centre of the village and along the narrow streets full of cafes, restaurants and shops.

Montepulciano

Your first day concludes in Montepulciano, the land of the Vino Nobile, the noble wine. The road from Bagno Vignoni is about 26 km and will bring you through some interesting places. Don’t worry, you’ll be back in this area on the second day.

Just before arriving in town, stop at the Temple of San Biagio. This church, unfortunately, opens quite late in the morning. If you manage to visit in the afternoon, you’ll waste no time the following morning.

The church, built in Renaissance style, is a place of great interest. The unmissable part is behind the altar, inside the marble reredos, where you can see the fresco of the Madonna Enthroned with Child. This work of art is bound to some miraculous events.

Once outside the Church of San Biagio, you should devote what’s left of the afternoon to get settled for the night. If you feel like it, you can take a stroll in the city centre before or after dinner.

For the night, we decided to stay at the Agriturismo il Sasso. It’s a lovely facility a few kilometres outside town. The price, 50 euros per room per night more or less, makes it a perfect and low-cost solution, even if you’ll have to go to Montepulciano by car for dinner.

For your quick evening tour, I suggest you park your car nearby Piazza Don Luigi Manzoni. It’s situated near the lower entrance to the city centre. This way you’ll be able to visit the lower part of town and some of the most charming streets. One of them is the well known Corso.

Along the Corso, you’re going to find several restaurants, such as La Vineria, La Pentolaccia and the Trattoria di Cagnano. Since we couldn’t find a table at La Pentolaccia, we had dinner at the Trattoria di Cagnano. It’s a cosy and low-cost restaurant, serving tasty local dishes.

Day 2

The second day starts with a visit to Montepulciano. This time, however, you’ll focus on the upper part of town. The nearest parking lot is near the Porta di San Donato. If you start early in the morning, you won’t have any difficulty in finding a spot for your car.

In this part of town, you’ll be able to see some of the most characteristic buildings such as the Medici Fortress, the City Hall and the Cathedral of Santa Maria Assunta. Among the others, the most important is the City Hall, built between 1300 and 1400 and overlooking Montepulciano with its Civic Tower.

Monticchiello

The next stop of the tour is Monticchiello, a small medieval hamlet where time seems to have stopped. The journey to reach Monticchiello from Montepulciano, despite the short distance, isn’t quick. In fact, you’ll have to drive along some dirt roads.

The visit of Monticchiello is going to be quick, however, take the right time to admire the place and enjoy the peace of the village, one of the most beautiful in the whole Orcia Valley.

Pienza

We’ve finally arrived at the most influential town in the Orcia Valley—Pienza. The importance of this place is entirely due to the personality of Pope Pius II Piccolomini. He hired the architect Bernardo Rossellino to realize the renovation project of the small hamlet where he was born. He aimed to transform the small hamlet in one of the most important towns in Tuscany. The renovation works built a Renaissance city, which, however, remained unfinished due to the untimely death of the Pope.

A singular aspect of the beauty of Pienza is that has made way for the Orcia Valley to become part of the UNESCO World Heritage. In fact, the centre of Pienza became part of the UNESCO eight years before the entire Orcia Valley.

The most fascinating part of Pienza is Piazza Pio II, where you can see the most significant buildings, such as the Dome and Piccolomini Palace.

Even if the Pienza Dome isn’t particularly fascinating, it’s unusual if considered inside the project of the Rossellino. The famous Florentine architect transformed the entire square. He built the Dome, giving it a different orientation and placing it overhanging the hill so that the square was as wide as possible.

Piccolomini Palace, instead, is far more fascinating than the Dome and can be visited through one of the many guided tours. During the visit, you can admire the rooms on the first floor, fully decorated and furnished with period furniture. Another beautiful part is the hanging garden, the most ancient of the Renaissance. Unfortunately, you can’t take pictures inside, however, in fine weather, you can enjoy a fantastic view over the Orcia Valley from the garden or the loggia on the first floor.

Before leaving Pienza, don’t forget to take a stroll along Corso Rossellino, the main street in Pienza. Here you can find several shops of souvenirs and local products.

For lunch, we choose a solution, both cheap and delicious. We stopped in a shop and bought sandwiches with the renowned Pecorino di Pienza in its various stages of seasoning. Then we brought the sandwiches with us to the next stop.

Chapel of the Madonna di Vitaleta

A few kilometres beyond Pienza, there is an unmissable stop on fine weather. It’s a small church called Chapel of the Madonna di Vitaleta. To reach the chapel, you need to leave the main road and drive along a dirt road. You’ll have to park your car at some distance from the chapel. With a short walk, you’ll be able to reach the chapel. Visiting the inside isn’t easy, because it’s almost always closed. However, this detour is worth your time. The beauty and the peace reigning here makes it one of the symbols of the Orcia Valley.

San Quirico d’Orcia

The last stop of the tour is San Quirico d’Orcia. Even if this small town doesn’t have the charm of other villages in the Orcia Valley, it’s worth a short visit nonetheless.

The most interesting part is Via Dante. Where the historic centre begins, you’ll find the Horti Leonini. It’s a huge Italian garden built around the end of 1500 not for private use but as a place open to the public and dedicated to the pilgrims travelling on the Francigena Way. On the opposite side of Via Dante, you can see the Collegiate Church of San Quirico. Despite the several renovations during the centuries, it still maintains some of the characteristics of the 1300 structure.

Return to Siena

After visiting San Quirico d’Orcia, it’s time to proceed towards the next destination—Siena. If you are tired or it’s late, you should take the road SR2, that will bring you to Siena in an hour. If you still have some energy, you can make one last detour through Asciano. This way you’ll be able to go through the area of the Crete Senesi. Among the hills, you’re going to see other beautiful landscapes and charming panoramic views of Siena.

As I already said, our next destination is going to be about Siena.

I hope you enjoyed this tour of the beautiful Orcia Valley.

See ya!