A destination guide to Val D’orcia

7 June 2023
Written by
The Italy Insider

Where to go and why

Sweeping valleys that change colour according to the season and the colours in bloom – from deep greens to bright reds in poppy season, to sheets of sunflowers that disappear into the distance. The Val d’Orcia is THE destination everyone dreams of, to drive along the windy roads in a vintage convertible as the wind brushes through your hair, passing cypress trees beautifully lined up as if they were in a painting. There are a few areas in the Val d’Orcia territory that conserve fascinating sites, wonderful wine cellars and hidden gems to sleep in and wake up to complete bliss.


An antique and renowned medieval village located in the province of Siena, the heart of the Val d’Orcia, that is part of the UNESCO Heritage. San Casciano dei Bagni is known for its 42 natural thermal springs which, thanks to their healing properties, were much loved by the Etruscans and Romans. The beauty of San Casciano dei Bagni is that original buildings, churches and small alleyways still retain and preserve their original medieval structure.

Where to eat

La Fontanella

The restaurant is located in the peaceful and calm hillside within La Fontanella Hotel. The menu is very traditional, paying particular attention to the quality and seasonality of the ingredients produced in the region. Homemade pasta accompanied by a glass of local wine is the recipe to pure happiness. WEBSITE

Where to sleep


Located in the heart of the Val d’Orcia, near Siena, Fonteverde is a historic palace placed over a mineral spring. This hotel boasts extraordinary panoramic views as well as professional treatments and massages aimed at regenerating and recharging your energies. Sleep in the timeless, period decorated rooms and open your window out to the purest source of energy: nature. Spend the day in the holistic spa and swim in the thermal pools overlooking the wonderful backdrop. Heal your soul with one of the Oriental therapies that combine ancient Indian medicine with the therapeutic properties of hot springs such as an ayurvedic massage or reflexology or perhaps explore the benefits of natural rituals from thermal mud mousse packs and essential oils. There are also diet programmes and programmes aimed at helping you rebalance your physical and mental wellbeing. WEBSITE

Fonteverde swimming pool


The history of San Casciano dei Bagni revolves around the important thermal springs, probably used before by the Etruscans and then mostly by the Romans. Take a trip to Bagno Grande, an area with 42 thermal springs with a natural temperature of 42 degrees, making this location the 3rd in Europe for thermal water flow. 


Located in the southern part of Siena, Montalcino is surrounded by 13th century walls that were used to protect the village. Surrounded by secular olive trees and ancient oaks the landscapes are typical of the region. Within Montalcino you’ll also witness the 14th century Fortress that stands proud over the village, worth a visit. The town also become renowned around the world for the Brunello, a noble red wine that’s paired beautifully with a steak.

Abbazia di Sant’Antimo

What to see

Museo Tempio del Brunello

The museum is an innovative and immersive destination that evokes the history of its surroundings as well as the evolution of its vineyards that have made their way into the international markets. You can take a seat in the cloister and watch a short clip that transports you across castles, villages, vineyards and hills of Brunello di Montalcino. The visit ends at the Digital Enoteca Bistrot Tempio del Brunello where you’ll learn about the different types of Brunello di Montalcino (Vintage, Vineyard and Reserve) and Rosso di Montalcino. You’ll also. be guided by a digital sommelier who will help you chose which Brunello to taste according to your preferences. Each tasting will be accompanied by a tasty Tuscan menu by Imma Cordella.

Where to eat

Alle Logge di Piazza

A typical Tuscan osteria located in the central Piazza of Montalcino. Here, you’ll taste traditional cuisine within the rustic ambiance of the restaurant.

Albergo Ristorante Il Giglio 

Ristorante Il Giglio is located in a refined and historic hotel in the city center. There’s a tasting menu with five courses that change according to the season – but always expect local flavours such as Chianina beef, truffle, pigeon, and Val d’Orcia cheese. WEBSITE

Osteria di Porta al Cassero

Osteria di Porta al Cassero is a traditional restaurant with a warm, cosy atmosphere. An array of typical antipasti to get the hunger going (a selection of bruschette are always the ones) and among the first courses chose between two home pastas: Pici o Maccheroni – and then select your favourite sauce. WEBSITE

Locanda Demetra

An intimate farmhouse where you can book a cooking class or simply savouring farm-to-table cuisine in the family dining room. The menu features homegrown produce (or locally sourced) coupled with a glass of their own produced, natural wine. Surrounded by a garden, during the warmer days you can chose to eat under the pergola or request a picnic and find a secluded spot to enjoy your lunch in intimacy. WEBSITE 

Wine Tasting

Gabriele Gorelli, from Montalcino, was the first Master of Wine of Italy. In this destination you can live in his legacy and taste some of the best wines in the region. Every year a chemical-physical and organoleptic examination of a wine sample is carried out in January, in order to understand the quality of the harvest. Starting from 1992, every year the Consorzio del Vino Brunello di Montalcino creates a tile to position on the wall of the town hall of Montalcino to celebrate the harvest.

Tenuta Carpineto

Tenuta Carpineto

Tenuta Carpineto is a winery that houses five estates and over 500 hectares of land. Here, around 95% of their production is red wines, among which, in the Montalcino estate, is Brunello di Montalcino and Rosso di Montalcino, both made with Sangiovese grapes. Here you can book a wine tour & tasting to experience the territory and their methods of production alongside tasting some high quality reds. WEBSITE

Tenute di Biondi Santi 

The Tenuta di Biondi Santi is the first producer of Brunello in Montalcino. It all started with Clemente Santi and his nephew Ferruccio Biondi Santi who in the eighteen hundreds began to produce barrel-aged single-varietal wines in Montalcino and, in 1888, produced the first vintage Brunello di Montalcino. WEBSITE

Where to sleep

Rosewood Castiglion Del Bosco

One of the suites at Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco spans across 2000 hectares, housing 42 rooms & suites, 11 villas, two restaurants, a SPA, Golf Club and Wine Cellar. The design, curated by Teresa Burgisser and Chiara Ferragamo, is charming: an elegant spin on antique furnishings with a careful colour coordination in each room. technologies. Behind the beautiful interior design of the hotel, there are Teresa Burgisser and Chiara Ferragamo. The hotel also offers a Spa where you can relax enjoying the treatments and private garden. The Rosewood Castiglion Del Bosco also has some independent villas with beautiful pools and amazing gardens located on a private hill. There is also a private wine cellar with a collection of their wines including those purchased by Justin Timberlake and his wife, and a golf court, the only private one in Italy with a clubhouse. WEBSITE

castello banfi

Among Sienese vineyards and olive trees, Castello Banfi is renowned for the undisputed quality of its wines as well as its exclusive Il Borgo hotel and two restaurants: La Sala dei Grappoli and the Taverna Banfi. The little 18th century hamlet in which the fourteen rooms and suites are situated preserves entirely the original structure and charm of what used to be the the dwelling of farmers who toiled for the noble landowners. After renovations, each room acquired a unique personality with an interior design signed by Federico Forquet who was able to enhance the simplicity of the place, preserve its soul, and at the same time provide a luxury feel. The swimming pool is on a terrace, overlooking the magnificent Val d’Orcia. Do not miss a visit to the cellars of the company and to the Glass Museum in the stables of the Castle. WEBSITE

Borgo Finocchietto 

Borgo Finocchietto is an exceptionally charming hamlet immsersed in the Tuscan countryside and placed on the Via Francigena, the medieval pilgrimage route from Canterbury to Rome. Borgo Finocchietto is made up of the main manor house Villa Finocchietto with nine suites and an ancient cobble-stoned courtyard as well as four independent villas which in total can accommodate upto 44 guests – perfect for weddings or events! Surrounding the buildings are perfectly trimmed gardens and mesmerising views. Here, savour seasonal cuisine by Tuscan Born Chef Roberto Rossi with the option of buffet or sit-down dinners as well as many more excuses to enjoy local delicacies and wine. WEBSITE


Visit the old medieval town of Montalcino, passing by the Fortezza, the Dome, the Church della Madonna del Soccorso and simply immerse yourselves in the beauty of the small cobblestone streets that will take you back to the medieval times. 


Immersed in the green hillsides of the Val d’Orcia, Montepulciano is a paradise for wine connoisseurs and not only. It’s the heart and soul for anyone who loves a good glass of full bodied red. The historic center leads up to the Piazza Grande that withholds unique historic pearls such as the Palazzo Comunale, Pozzo dei Grifi e dei Leoni and an array of renaissance structures. 

Where to eat

La Solita Zuppa

Located in Chiusi, near Montepulciano, the restaurant La Solita Zuppa has a long history of tradition and hospitality. At first, the space was a point of reference for all the surrounding countryside villages who would sell their freshly picked produce. However, later on, it evolved into a space where you could share and taste the culinary traditions of the Tuscan region. A welcoming and warm atmosphere, where you can try typical dishes and soups (as you know Pappa al Pomodoro or Ribollita are two very traditional tuscan dishes) that put in the first place the quality and craftsmanship of the territory. WEBSITE

Wine Tasting

Cantina Ercolani

Cantina Ercolani, a wine cellar located inside an ancient underground city, can be accessed from its shop. Private tours are organised here: an underground itinerary connects the cellars of seven Renaissance palaces with stops at the ancient oil mill, the stable, the vinsantaia (it’s a room where the sweet wine is made), the cheese room and a part with a museum of instruments of pleasure and torture, and two Etruscan tombs. They produce: Nobile di Montepulciano, the first Italian DOCG born in 88. WEBSITE

Where to sleep

Il Borghetto 

Il Borghetto is a historic villa that was passed along many families until becoming the property of the Savoia dynasty. In 1999, the villa was purchased by the Bimbi family who, after careful renovations, created elegant apartments in which you breathe timeless Tuscan style with windows that overlook the uncontaminated countryside. WEBSITE

A view from Montepulciano


Get lost in the beauty of the old medieval alleys of Montepulciano and stop by the historical structures. From the Santa Maria Assunta Cathedral, passing by the Piazza Grande and finally admire the Fortress that overlooks the town of Montepulciano. Also take time to visit Poliziano, one of the most iconic and historic wineries of Montepulciano. WEBSITE


Castiglione d’Orcia is immersed among rolling hills, cypress trees and gullies. Here art is at the centre of the small town whose main square “Piazza Vecchietta” is dedicated to Lorenzo di Pietro, a renowned artist from Castiglione d’Orcia.

What to see

La rocca di Tentennano

La Rocca di Tentennano is the only fortress tower in Val d’Orcia. Before the 11th century, it was one of the main outposts on the Via Francigena, offering a 360° view from Monte Amiata across the entire Val d’Orcia. You can book a tour through ValdOrciaTour, climbing to the top of the tower and enjoy the sensational panorama. Below the tower is Rocca d’Orcia, a small medieval village of Etruscan origins, with a few houses arranged in a fan shape around the central square where you can stop for a bite to eat or sleep at the Cisterna del Borgo.

Where to eat

Osteria Perillà 

Contemporary and tradition come together at Osteria Perillà, with refined and simple proposals that seek to bring a little newness to the table in which traditional flavours are enhanced with locally sourced ingredients. WEBSITE

Pasticceria Artigianale Scheggi

In Borgo Vittorio Emanuele, in the heart of Castiglione d’Orcia, a sweet stop at Pasticceria Artigianale Scheggi is a must. Each delicious thing is carefully prepared by the highly talented Dario Scheggi. WEBSITE

Where to sleep

Relais Osteria dell’Orcia

An idyllic place situated among antique Tuscan villages, secular olive and cypress trees surrounding Relais Osteria dell’Orcia and it’s well known restaurant La Vecchia Posta. Sixteen simple, essentially furnished rooms that lead out onto the picturesque garden and swimming pool framed by uncontaminated nature. Conveniently close to Bagno Vignoni springs. WEBSITE


Castiglione d’Orcia is a charming village that extends in between the hills of the countryside. Visit the center of the scenographic town, from the Piazza Vecchietta dedicated to Lorenzo di Pietro, an artist from the village, to the Rocca Aldobrandesca built on top of the townhouses by the feudal family. 


Pienza is a hilltop town with a distinct character that encloses some cultural and architectural gems. The central Piazza Pio II is framed by 15th-century buildings like the Pienza Cathedral and Piccolomini Palace which also become Pope Pius II’s summer residence. From its pecorino cheese to sweeping views across the valley through charming cobblestone streets, Pienza is a “must” destination to visit during a stop in the Val d’Orcia.

What to see

Castello di Spedaletto

During the early and late Middle Ages, the importance of the Val d’Orcia was linked to Via Francigena, an ancient road that crossed the entire country and used as means of communication and commerce. Along here, many “Spedali” or shelters were built such as Castello di Spedaletto, which later became a farm of monastic property. Today, the castle stands majestic with towers at every corner and a fortified access door beautifully preserved. You can access the external courtyards and the church for free, as well as booking lunch at the Locanda del Mulino, a small restaurant in which local recipes are made with ancient stone-ground grains from the Val d’Orcia mill, a farm that produces pasta, stone-ground flours, cereals, legumes, wine and oil which is also open for visits. WEBSITE

Where to eat

Podere il Casale

Podere il Casale

A menu based on local and biological ingredients coming from the territory. Meat coming from their farms, freshly made pasta, cheese, olive oil and honey all come from their productions. With the philosophy of preserving and respecting their territory to produce food for their guests Podere il Casale is a km0 restaurant with a beautiful panoramic terrace. WEBSITE 

Where to sleep

Relais Il Chiostro di Pienza

An ex-Franciscan convent of the 13th century designed by Rossellino under the will of Papa Pio II Enea Silvio Piccolomini, located in Pienza, a beautiful village at the center of the Val d’Orcia. Relais Il Chiostro di Pienza is an elegant and refined hotel with an antique and typical spirit in its suites. WEBSITE

Villa Pienza

A traditional countryside home, built with stones, completely immersed in the green lands of the Val d’Orcia. A perfect place for a slow vacation with all its comforts; a panoramic swimming pool, elegant rooms and a breathtaking view that extends from Pienza to Montalcino. With its natural materials, old oak floors and soft colors that respect its surroundings, making your stay even more relaxing. WEBSITE

Top Tip

Visit the small historic center of Pienza and try their traditional pecorino, a specialty of the territory seasoned in barriques – you can find this delicacy at Marusco e Maria. On your journey make sure to visit il Duomo di Pienza, where ‘The Assumption”, by Lorenzo di Pietro, a local artist, is displayed. WEBSITE


This small yet fascinating village sits in a land full of history and culinary traditions all to be discovered. San Quirico is an old town with Etruscan origins immersed within harmonic landscapes and endless historical references. It has a small and cohesive historic centre that houses the Collegiate Church of San Quirico, worth a visit – as is the Horti Leonini which in summer welcomes numerous art installations.

Where to eat

Ristorante Fonte alla Vena

This restaurant is an intimate and romantic endroit with rustic interiors and a pleasant courtyard. The menu features an array of traditional dishes or “cucina povera” that can be enjoyed with an excellent selection of wines. WEBSITE

Trattoria Osenna

Trattoria Osenna is known as the oldest restaurant located in San Quirico d’Orcia. In the beautiful garden of the trattoria enriched by secular wisteria, you will be able to taste traditional dishes using high-quality ingredients coming from the territory. WEBSITE

Where to sleep

Agriturismo il Rigo

Il Rigo is an old farmhouse constructed in stone and bricks that sits on one of the most peaceful hillsides of the Tuscan landscape. Today the secular farmhouse wishes to open its doors to its guests to make them live an authentic experience, delving into the culture of the land. The rooms and suites recall the simple and familiar look of a countryside house, with antique furniture and an amazing view of the valley. Il Rigo also offers a restaurant that serves traditional Tuscan dishes, using biological and local products. WEBSITE 

Agriturismo Il Rigo


With its Romanesque style, built on the remains of an ancient church, La Collegiata dei Santi Quirico e Giulietta is a beautiful historic construction to not miss out on while visiting San Quirico D’Orcia. Inside you will see, behind the altar, one of the most important artworks of the town, the back of the choir that was embellished by Antonio Barili.  


A small village with a magic atmosphere that you can perceive in all its tiny medieval alleys. A perfect destination for those who love a slowly pieced vacation enjoying the scenographic valleys that outline Monticchiello. Get lost in the medieval village and see the Pieve dei Santi Leonardo and Cristoforo and the Romanesque Church. 

Where to eat

Ristorante Daria

Ristorante Daria is located in the main alley of the medieval town of  Monticchiello. Here you can taste authentic Tuscan cuisine with a touch of innovation given by the creative thought of the chef. From March to November you can also take part in a 2hr cooking class and learn to make traditional recipes which you’ll be able to taste following the session. WEBSITE

Where to sleep


A beautiful countryside home that is in complete harmony with its green and absolutely relaxing surroundings, that remained intact since the Middle Ages. L’Olmo is a small farmhouse located in the heart of the Val d’Orcia, more specifically in the small town of Monticchiello. The hotel is directed by Tonino Cacace, former owner of Capri Tiberio Palace and Sara Iannuzzi. Built in the ‘600, the estate has been renovated whilst still maintaining original elements such as the wooden beam ceilings. WEBSITE


The Teatro Povero di Monticchiello was originally born in the ‘60 as a social and cultural project for the population. At the time the village was going through a period of crisis, which saw a great deal of people leaving and moving to bigger cities. A big shift to modernity was taking place and with this, culture and traditions were being lost. For this reason, the town of Monticchiello decided to create the theater in the main piazza, to stand together against the crisis. 

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