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Montalcino and his view on the Val d'Orcia

Text Teresa Favi

September 8, 2021

Montalcino. What to see, where to eat and sleep in the town of Brunello

Our tour of Tuscany's most beautiful areas takes us to the town of Tuscans's most famous wine in the world

We are in the home of Brunello, the most famous Tuscan wine in the world. From the top of Montalcino you can see the entire Val d'Orcia. We are perched on a hill south of Siena, at the foot of which the abbey of Sant'Antimo stands in a timeless setting, while famous vineyards surround its flanks. Compared to other Italian wine areas, this one is a handkerchief. For this reason it is even more prized and coveted.

The origins of Montalcino date back to the Carolingian period (7-800 AD). Due to its strategic position, on a hill 560 m above sea level, during the communal period, the town was the object of frequent attacks by nearby Siena, in perennial contention with Florence. After the historic battle of Montaperti in 1260, Florence ceded Montalcino to Siena. Arts and crafts flourished in the town and around the 15th century the town took on its current urban organisation.

In addition to the splendid panorama of beautiful countryside and hundreds of hectares of vineyards and Mediterranean scrub, there are many testimonies to the past: the ancient walls with six gates, the pentagonal fortress of 1361 that dominates the town with its mighty mass, the 13th century Palazzo Comunale, the 14th century church of Sant'Agostino with frescoes of the Sienese school, the ancient convent of San Francesco with its tower built in 1287 and 16th century cloister.

Of great interest is the Cluniancense Abbey of Sant'Antimo, founded, according to tradition, by Emperor Charlemagne in 781, an authentic Romanesque masterpiece, a white mirage in the middle of the vineyards.
Montalcino is also home to one of the most important museums in southern Tuscany, rich in paintings of the Sienese school, polychrome wooden statues from the 15th century, a Crucifix from the end of the 1100s from Sant'Antimo and its medieval ceramics.

As soon as you arrive in Montalcino, we recommend a visit to the Fortezza where, on a clear day, you can enjoy a 360-degree panorama as far as the eye can see. There is a fantastic wine shop inside the Fortezza. The best place to enjoy a truly spectacular sunset is on the west side of Montalcino, along the avenue from the Fortezza to the Church of the Madonna del Soccorso.

Another address not to be missed in the area is the Castello di Poggio alle Mura with its adjoining glass museum, now owned by a winery. Not forgetting the 19th-century Caffè Fiaschetteria in the town's main square, classified as one of Italy's historic establishments, the excellent panpepato of the Lambardi bakery and Rossano Vinciarelli's pastry shop in Montalcino... dive into his ricciarelli.


Pienza There is no better definition of Pienza than the words dedicated to it by Pascoli: "born from a thought of love and a dream of beauty".

Bagno Vignoni. The old town centre is unique: instead of a square, there is a large pool of thermal water where Saint Catherine of Siena used to go for treatment in the 14th century and where Tarkovsky shot the most evocative scenes of the film Nostàlghia.

San Quirico d'Orcia Above the remains of the ancient village of Osanna rises the village that has defined the archetype of the Tuscan landscape: its cypresses are the most photographed in the world.

Abbey of San Galgano. A Gothic mirage that appears out of nowhere among the curving country roads, with the mystical charm of the union between heaven and earth due to the absence of a roof.

Monticchiello. A typical medieval village nestled in the Sienese countryside, famous for the historic tradition of the Poor Theatre in which all the inhabitants are authors and actors.


Hotel Restaurant Il Giglio. This restaurant in the heart of the village of Montalcino - in a small family-run hotel - has over 120 years of history. Tuscan cuisine (lightened up), encyclopaedic wine list and fair prices.

Enoteca Osteria Osticcio. Traditional and refined cuisine.
Fabulous wine cellar. Three dishes not to be missed: the anchovies under pesto, the spinach carbonara, the sausage with Casentino fried egg with potato and bacon pie. In the back room there is a giant window with a breathtaking view. A must!

Taverna del Grappolo Blu. Informal atmosphere and rustic tone, very enjoyable: from crostini and typical cold cuts to tagliolini with truffle cream and mushrooms, from pici with garlic sauce to beef cheek with Brunello wine.

Osteria di Porta al Cassero.
This restaurant is located on the site of old stables, with a regular bar and stylish furnishings. The antipasto misto with bruschette is a must, and the house wine is not bad.

Drogheria and Locanda Franci. Wine cellar that reaches into the basement with a spiral staircase, carefully prepared cuisine where even nouvelle cuisine dishes are not served in nouvelle cuisine quantities: try the octopus on chickpea cream, lasagna with porcini mushrooms and pigeon.

Vineria Le Potazzine. Open from late morning until sundown, like French brasseries. Aperitifs and snacks with platters and croutons, accompanied by a glass from the always interesting and well-stocked wine list. At lunch try pappa al pomodoro and peposo.
In summer, you can eat outside in the lounge of Piazza Garibaldi.

Boccon Divino. A spatial view from the terrace of a family-run restaurant that convinces on two fronts: tradition, with a peposo and a steak of value, and moderately creative.

Rosewood Castiglion del Bosco. In the splendid estate of Massimo and Chiara Ferragamo there are two restaurants that live up to expectations, both run by the young chef Matteo Temperini, an emerging outsider who you will soon hear about.
you will soon hear about. This year, for the first time, they are also open in autumn and for the Christmas holidays. One is more gourmet, the Campo del Drago Restaurant, named after one of the estate's best wines, where you can dine on the terrace while admiring an incomparable view of Montalcino. The other is Osteria La Canonica, a seasonal and fresh menu, with dishes that smell of flowers and spices, such as lavender that becomes a sauce to savour. And also pizza with ham and figs cooked in the new wood-fired oven.

Taverna dei Barbi. Medieval furnishings, tapestries, curtains and low lighting: a place of great class and fine cuisine, from starters to desserts. In season, game dishes are always recommended.

Da Roberto alla Taverna di Montisi.
An authentic host, who gives his name to the restaurant and juggles the dining room and kitchen. Great products - such as cheeses and vegetables - and simple cooking. A different experience.

Trattoria Il Pozzo. Set among the stones of the historic centre of Sant'Angelo in Colle, this restaurant has existed since 1968. Everything is handmade, from tortelli to pici and desserts. The pici all'aglione and onion soup are an excellent prelude to the spectacle of grilled meats.

Trattoria Il Leccio. The interior is beautiful, with medieval walls, candlelight, the scent of embers and a fireplace. Prosciutto and figs to start, continue with a ribollita and then you can lose yourself in the meat menu, they have certified Chianina IGP. In summer you can eat outside in the main square of Sant'Angelo in Colle.


Rosewood Castiglion del Bosco. An entire medieval village transformed into a luxury hotel with a village equipped with small craft shops, gourmet restaurants, a golf course and a wine cellar with the private cellars of the top guests, who keep their bottles stored there, as if in a vault, so they can taste them there. Now extended with 19 luxury suites.

Castello Banfi Il Borgo. Among vineyards and woods, it offers a refined environment where you can relax and discover engaging multi-sensory experiences between two restaurants, the wine shop, the glass museum and the unique landscapes of the Sienese countryside.

Casanova di Neri Relais. An old farmhouse and barn on top of the hill overlooking the winery. 10 meticulously and authentically restored suites and rooms in a perfect fusion of ancient and modern, luxury and comfort.

Hotel Il Giglio. Converted from an ancient palace built close to the castle walls of the city of Brunello, right at the point where a dizzying view overlooks the Crete and Siena, this is a small, family-run hotel where passion and simplicity are the watchwords.

Castello di Velona. It has become a super luxury hotel that boasts 3 magnificent restaurants (Dolce Vita, Brunello and Settimo Senso) and a bar with one of the most beautiful views in Tuscany. Plus, there's also a natural spa and a panoramic thermal pool...not bad at all.

Villa Centinale. One of the finest examples of Roman Baroque style, by English MP Sir Antony Lambton. It has 13 bedrooms and can also be rented entirely for private events or holidays.


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