top of page
  • Immagine del redattoreVanessa Valenti

Weekend in Tuscany to discover the wonderful Val d'Orcia, San Gimignano and Volterra

This area of ​​Tuscany is perfect for an all-Italian weekend: we left on Friday afternoon and went back home on Sunday evening. Obviously, for an in-depth visit, which also includes the interiors of churches and monuments, it takes a few more days, depending on what type of trip you want. We visited many things in a short time, including wine tastings and lot of typical dishes. The strategic position of Montepulciano makes it the ideal place to set out to discover this beautiful corner of Tuscany: Pienza, the spa village of San Filippo, the famous Montalcino and many other villages are all easily reachable in a short time. This is why we chose Montepulciano as the first stop on this tour in Val d’Orcia, San Gimignano and Volterra for a friends weekend.

Let's see our itinerary:

  • Montepulciano

  • San Quirico d’Orcia: Cappella della Madonna di Vitaleta - Cipressi Ring

  • Pienza

  • Bagni di San Filippo

  • San Gimignano

  • Volterra


Located on the top of a hill, in the south of Tuscany and not far from Siena, Montepulciano is a medieval village of rare beauty, with elegant Renaissance palaces, ancient churches, splendid squares and small hidden corners, not to mention the breathtaking panorama over the Val d 'Orcia and the Val di Chiana. Montepulciano has Etruscan origins but it really reached its peak during the 16th century, under the dominion of the powerful Medici family.

Montepulciano, Val d'Orcia, Toscana

Our visit to Montepulciano began from Porta al Prato: the city is enclosed by ancient and imposing walls and it's crossed in the center by the Corso, the main road, from which narrower alleys and streets branch off. The Corso di Montepulciano is a refined sixteenth-century street, home to many patrician palaces, and consists of the three segments of the streets of Gracciano, dell'Opio and Voltaia. In via Gracciano, where our hotel was located, on a staircase with a balustrade we find the fifteenth-century church of Sant’Agostino and in Piazza Michelozzo you will notice the famous Pulcinella Tower with the typical mask that beats the hours. But the heart of Montepulciano is Piazza Grande: all around we find some of the most beautiful palaces, including the Cathedral which is an “almost copy” of the Palazzo della Signoria in Florence. Piazza Grande is considered the "Pearl of the sixteenth century" and has hosted various international productions including the TV series "Medici - Master of Florence" but also "New Moon" of the Twilight saga.

We spent the afternoon among the alleys of this splendid village and we ended with a fantastic tasting of wines and typical products of the Val d'Orcia, which we will talk about shortly, and an excellent dinner just outside Montepulciano. In the night we did an amazing tour of some winery in the city centre, tasting a glass of wine in each one. But let's now conclude our visit to Montepulciano, with the Temple of San Biagio, un unmissable: a masterpiece by Angelo da Sangallo, it's the tallest building with a Greek cross plan of Renaissance architecture. The Temple stands in the middle of a meadow just outside the village, easily reachable with a 10min walk from the center or even by car, which is why we kept it for Saturday morning in order to reach it by car and then from there we kept on the our tour of the Val d'Orcia.

Where to sleep in Montepulciano

Guesthouse Via di Gracciano, Montepulciano, Val d'Orcia, Toscana

For the first nigh of this mini-tour we stayed in the center of Montepulciano, in order to visit the village on Friday afternoon, and to be able to leave in the morning after a visit to the Temple of San Biagio, direct to the Chapel of the Madonna della Vitaleta. We stayed at the Guesthouse Via Di Gracciano - Adults Only (83 € for a double): the location was fantastic, in the historic center, and the room was delightful and very spacious. The owner was very nice and gave us a lot of useful information, and also a map of the village with all the most important attractions. We left the car in Parking 1-P1, just outside the door to the Prato: in the evening you don't pay.

Where to eat in Montepulciano

Together with Montalcino, Montepulciano is known for the great production of red wine: its Nobile di Montepulciano, one of the most appreciated wines both in Italy and abroad, you can taste it in one of the numerous small wine bars scattered around the village. Many have a panoramic terrace, from which you can admire the splendid panorama over the Val d'Orcia. There are also tons of opportunities to have wine tastings and visit wineries. I absolutely recommend that you try this extremely characteristic and typical experience of the area.

Cantina Gattavecchia

Cantina Gattavecchia, Montepulciano, Val d'Orcia, Toscana

We had a wine tasting at sunset at Cantina Gattavecchia, easily reachable on foot from the historic center, it was amazing. The winery has a splendid panoramic terrace where we had our tasting in time for sunset, enjoying a breathtaking view of the Val d’Orcia.

This alone was worth the visit, but they also have an exceptional menu. We ordered a mixed platter of local cold cuts and cheese, accompanied by glasses of Nobile: needless to say that it was all very good.

The price is not exactly cheap but it's worth it, considering that a visit to the immense cellar was also included.

La Dogana Enoteca, Val d'Orcia, Toscana

La Dogana Enoteca is a little place 15 minutes by car from Montepulciano, which is worth the whole way! You can stop for an excellent tasting of Nobile di Montepulciano or to taste the products of the Tuscan tradition in a splendid and well-kept location. The restaurant is located on a hill, from whose garden you can enjoy a splendid view of the valley. The menu changes from season to season, focusing on the products of their garden. You can choose between the various single courses or the menu with or without wine tasting. In any case, I recommend it to you at sunset, even if it maintains its charm even when it gets dark.

We ate divinely, and despite the excellent value for money, the bill is a bit salty.

San Quirico d’Orcia

On Saturday morning, from the Temple of San Biagio di Montepulciano, we headed towards San Quirico d’Orcia, with two stops at the Chapel of the Madonna di Vitaleta and at the Cipressi Ring, before taking a short walk in the center of San Quirico.

San Quirico d'Orcia, Val d'Orcia, Toscana

The village of San Quirico d'Orcia is located on top of a small hill, above the remains of the ancient village of Osanna, halfway between two other famous villages of the Val d 'Orcia: Montalcino and Pienza. The village still shows its original medieval structure and it's located within a characteristic wall, divided by the main street, Via Dante Alighieri. Just outside these walls you will find many parking spaces. There are four doors to the cities, if you enter through the northwest door you will immediately encounter the Collegiate Church of San Quirico and Giulitta, a splendid Romanesque church. Behind and next to the Collegiate Church, there's Palazzo Chigi, which today houses the municipality of the city. Continuing along Via Dante Alighieri, you arrive at Piazza della Libertà, the heart of San Quirico d’Orcia. Here it's worth visiting the Church of San Francesco, also known as the Church of the Madonna, which houses the terracotta statue of the Madonna, the work of Andrea della Robbia, moved from the nearby Vitaleta Chapel. Continuing along this street, you will find many shops and restaurants until you reach the Church of Santa Maria Assunta. Do not miss the well-kept Horti Leonini, a splendid example of Italian gardens, with access from the central Piazza della Libertà. From the fortified walls that surround the Horti, it is possible to enjoy an amazing view over the Val d'Orcia. We stopped for a couple of hours, more than enough for a nice walk through the alleys of the village and to admire the buildings from the outside. We then headed to Pienza just in time for lunch.

Cappella della Madonna di Vitaleta

Cappella della Madonna di Vitaleta, San Quirico d'Orcia, Val d'Orcia, Toscana

The Chapel of the Madonna di Vitaleta is located in the hills of the Val d'Orcia, on the road that leads from San Quirico d'Orcia to Pienza, and it's one of the most beautiful and evocative corners of this area of ​​Tuscany, protected by Unesco as a Heritage of humanity. You will find it among fields and rows of cypresses and it's dedicated to the Madonna who once appeared to a shepherdess. It's located on a dirt road and can be reached by following a small sign that from the main road, after 2km, you will find a space to park your car and finish the last 500m on foot. This chapel, small and lost among the fields of the Val d'Orcia, was for many years a place of adoration of the statue of the Virgin of Consolation, until 1553, when the famous statue of the Virgin attributable to Andrea della Robbia was moved. The statue, now preserved in the Church of the Madonna di Vitaleta in the center of San Quirico d'Orcia, has an interesting history: it's said that it was the Virgin, appearing to a shepherdess, who suggested that the faithful go to a shop in Florence where they would find the statue to be placed in the church of Vitaleta. The Chapel of the Madonna di Vitaleta is an unmissable stop on your tour of Tuscany: the scenery is incredible! If you have extra time I recommend a nice walk or a bike ride on the various paths in the hills of the Valley that pass through this area.

Outside the chapel there is a small bar, the Ristoro Vitaleta, which, although it's cute and suggestive, does not deserve it from the point of view of the menu. We tried it for breakfast and were quite disappointed.

Cypresses Ring - San Quirico's Cypresses

Cipressi Ring, i Cipressi di San Quirico d'Orcia, Toscana

South of San Quirico d’Orcia, a few kilometers from the town, you will see the famous group of cypresses arranged in a semi-circle. To reach them you can safely pull over on the road and cross it (being very careful!), reaching the Cypresses in a few steps .. the alternative is to go around from behind crossing the countryside and leaving the car in a parking lot a few hundred of meters from the semicircle, before a house. The road is unpaved and not very pleasant, so I definitely recommend the first alternative.


Pienza, Val d'Orcia, Toscana

Pienza is another splendid village in Val d’Orcia, also known as the city of Pope Pius II. Pienza obtained the recognition of a Unesco site in 1996 and is often defined as the "ideal city of the Renaissance" (or Utopia City): it was built in a very short time (about three years) becoming a complex full of beautiful and harmonious palaces, religious buildings and with a central square to be admired. Pienza is also famous for being the city of cheese! Pecorino of Pienza is a very tasty cheese, more or less aged, made with sheep's milk: the village is full of small shops that sell many varieties of pecorino, along with many other typical local products. We arrived just in time for a nice lunch based on typical products and then we dedicated ourselves to a nice walk through the historic center passing through Piazza Pio II, and the Duomo. Opposite, there is the Town Hall, dating back to the mid-1400s. Also in the square you will find Palazzo Borgia and the Museo-Palazzo Piccolomini with its hanging garden from which you can admire a splendid view over the entire Val d'Orcia.

In Pienza there are many beautiful corners, but the most beautiful is definitely Via dell’Amore: an alley that opens onto the breathtaking view of the Val d’Orcia.

Trattoria Latte di Luna, Pienza, Val d'Orcia, Toscana

Where to eat in Pienza:

In Pienza I absolutely recommend the Trattoria Latte di Luna, a small restaurant in the hand in the historic center of Pienza. They don't take reservations, but if you're ywo or three, they'll be able to find you a table in about ten minutes. In the meantime, you can go for a walk in the narrow streets of Pienza. Here you will find excellent dishes based on local products: there is no shortage of truffles and especially the pecorino di Pienza. The portions are huge and the value for money is excellent! I tasted some excellent bikes with white sauce with porcini, literally out of my mind, accompanied by excellent local wine.

Bagni San Filippo

Bagni San Filippo, Val d'Orcia, Toscana

From Pienza, we then moved to Bagni San Filippo, a small village famous for its natural springs, simply beautiful: the limestone formations, waterfalls and small pools of hot water are surrounded by the luxuriant nature of the forest, in an wild atmosphere. Access to the springs is free, so don't miss out on this place. Once the car is parked, you can reach the source along a path that runs along the river and allows easy access (please wear comfortable shoes and do not go in slippers!). The area is quite large, but the first pools you meet along the path near the road are shallow and less characteristic. Continue along the path in the woods to reach the impressive formations and waterfalls called "White Whale" due to their particular shape. From here you will find many swimming pools where you can sit and relax in the very hot water that flows from the ground at a temperature of about 48 ° C, which allows you to swim in both summer and winter. At the bottom of the pools you will find a rich deposit of thermal mud, perfect for face and body masks ... all for free!

San Gimignano

San Gimignano, Toscana

For dinner we finally moved to San Gimignano until Sunday morning. Declared a World Heritage Site by UNESCO in 1990, San Gimignano is one of the small pearls of the Sienese province which, thanks to an ancient law that prevented the demolition of old houses, it's almost identical to San Gimignano. medieval. If the Duomo is the religious symbol of San Gimignano, the Palazzo del Popolo is its civic counterpart: a few meters from each other, they are both located in Piazza del Duomo.

Rocca di Montestaffoli, San Gimignano, Toscana

Leaving the Duomo on the left, a small road will take you to the Rocca di Montestaffoli, built to defend San Gimignano from the attacks of Siena after its submission to Florence. Not much remains of the ancient fortress but it's worth reaching to admire an extraordinary view of San Gimignano and the Valdelsa. The only remaining tower of a complex defense system is the privileged point of view to enjoy the view.

Piazza della Cisterna, San Gimignano, Toscana

Piazza della Cisterna is an unmissable apot for every visit to San Gimignano: on the top of the hill on which the Tuscan town is built, it's an excellent place to rest after having covered the terrible climbs of the village. Always the "commercial square", here were the shops and rides; here there is also the Devil's Tower, so called because it's said that the owner, coming back from a long journey, found it higher .. who could have something like this in his absence if not the devil himself?

San Gimignano is a village full of activities, including the Torture Museum and many beautiful alleys where you can get lost, visiting the many shops of local handicrafts, you will be spoiled for choice. In particular, Vernaccia and Zafferano are very famous in San Gimignano, renowned all over the world. Saffron, also known as yellow gold, has repeatedly saved San Gimignano because it was used as a currency to pay off debts incurred during the wars with Siena and Florence. Vernaccia, a dry and harmonious white wine, has always been produced in San Gimignano, also appreciated by illustrious personalities such as Dante and Boccaccio.

Where to sleep in San Gimignano:

We stayed at Il Feudo (83 € for two), just outside the walls of the historic center of San Gimignano. Excellent place for its location: just a few steps from the center, and a convenient public car park is a few minutes' walk away. Here, too, you don't pay for the night, so we only had to insert a few coins for the following morning.

Where to eat in San Gimignano:

For dinner we stopped at the Osteria San Giovanni, located inside Palazzo Cugnanesi, a few steps from Piazza della Cisterna. Here you will find excellent traditional dishes of Tuscan excellence, as well as an excellent selection of wines from the best wineries in the area. Among the typical dishes of the place I point out the classic Tuscan crostini with livers, platters of local cured meats and pecorino, first courses with wild boar and second courses of meat. I tasted a very special beef tartare with saffron potatoes, rosemary oil and Val di Chiana garlic ice cream .. simply spectacular!


Before lunch, we left San Gimignano and, on the way back, we made a short stop in Volterra. Volterra is an old city in the province of Pisa, an ancient city-state of ancient Tuscany, Etruria. Its historic center retains its Etruscan origin: in fact, Porta Diana, most of the city walls, the Acropolis and the Porta all'Arco remain from that period, you will also find various buildings from the medieval period, such as the Palazzo dei Priori, the Medici Fortress and the Cathedral. The Etruscan Museum of Volterra houses an ancient archaeological find, considered among the most important in the world: a sculpture called by D'Annunzio "The Shadow of the Evening", which saw in its elongated shape the effect of the shadows at sunset. Another unmissable destination is the remains of the Roman Theater.

Where to eat in Volterra:

For lunch, as soon as you arrive in Volterra, we stopped at Cucina & Vino “Bono”, in the historic center. This small tavern with delightful tables on the street will offer you a wide choice of traditional recipes with local products. Typical of Volterra are the soup alla Volterrana, dishes based on mushrooms and truffles, game and wild boar, tripe alla Volterra and finally the classic panforte.

Here we are at the end of this weekend in Val d'Orcia: time was short, it was an improvised journey, we tried to see as much as possible. Obviously this land is splendid and rich in culture and splendid hidden corners in wonderful and ancient villages ... maybe a few more days would have been useful, but it was still a fantastic weekend of excellent food, rivers of delicious wine and lots of laughs with one of my best friends, so I wouldn't change a thing!

246 visualizzazioni0 commenti


Rated 0 out of 5 stars.
No ratings yet

Add a rating
bottom of page