Trequanda, Montisi & Castelmuzio

The land of olive oil, ancient hamlets dotted with Medieval towers and breathtaking sunsets



A town with quite a peculiar name, Trequanda, who’s origin we don’t know much about. Legend has it that the town is named after Tarkonte, a mighty Etrucan hero. This would coincide with the Etruscan archeological artefacts that were found in Trequanda, which are also the first signs of the area being inhabited. The names of nearby locations: Cennano, Sicille and Asso, also indicate an Etruscan presence.

Similarly to all neighbouring towns in Val d’Orcia, Trequanda was under the rule of the Ancient Roman Empire, followed by a Lombard and then Franc rule.

Trequanda is known for the beautiful terracotta objects produced in the area, a craft locals picked up after the two World Wars.

Perhaps the most renowned product to come out of Trequanda is its extra virgin olive oil. Due to a very unique ecosystem surrounding the town, olive trees thrive and produce a delicious, high quality olive oil.


Chiesa Parrocchiale dei Santi Pietro e Andrea

Sitting in Trequanda’s main square, the church was built in 1327 over a pre-existing church - something extremely common in the whole of the Christian world. Its peculiar facade is built in a chess-board manner, by alternating types of rock.

Image by wiki commons

Chiesa della Madonna della Rosa

Image by wiki commons

Built in 1700 and named after a nun, born in 1648, who used to pray in the location where the church was built. Legend narrates that after her death, in 1680, a rose kept on flowering where the church now stands.

Image by e-borghi

Rocca di Trequanda - Castello Cacciaconti

Image by e-borghi

A medieval castle and fort built with the purpose of being the headquarter of the Vicary for the Republic of Siena. A strategic position, as from above the Rocca’s tower one can see both Val d’Orcia and Val di Chiana.

Image by Associazione Nazionale dell'Olio


Image by Associazione Nazionale dell'Olio

May - Festa della Beata Bonizzella
October - Festa dell’Olio Novo
October - Festa della Birra

Image by @mornonico88


Il Conte Matto

traditional Tuscan

Savour Tuscan’s traditional dishes, from liver pate on toast to ravioli stuffed with Cinta Senese in a sweet cherry tomato sauce, all in a welcoming environment with a wonderful view, especially at dusk!


Image by Si Viaggia


Image by Si Viaggia

Montisi is a small hamlet perched on a hill between Pienza and Trequanda. The town’s name originates from the combination of the words monte (hill or mountain) and isi[de], the goddess to whom the Etruscan temple found in Castelmuzio is dedicated to. Literally translated, Montisi means “the mountain of Iside”.

As all other towns in Val d’Orcia, Montisi was under the rule of the Republic of Siena until its downfall, after which the small hamlet faced centuries of poverty, fortunately eliminated with the cultivation of saffron, which thrived in the town’s climate.

On the 30th of June 1944, during WWII, a troop of German soldiers blew up the Torre del Grancia, Montisi’s emblem, in the hopes of blocking the passage for enemies to reach them.

Following both World Wars, Montisi’s inhabitants began building back their town and lives by working in neighboring coal mines and by beginning to work with terracotta to produce various artefacts. A few years later Val d’Orcia was vastly inhabited by Sardinian shepherds who brought with them their sheep and cheese making knowledge, and promptly began producing Pecorino. The first foreign tourists began arriving in Montisi and the surrounding areas in the 1970’s, attracted by the undisrupted nature and sinuous rolling hills.

Image by wikipedia


Image by wikipedia

5th of August - patron saint festival: Giostra di Simone

A horse race between Montisi’s four different contrade. Each knight must centre, with their spear, a small circle placed on the shoulder of a dummy who represents Simone Cacciaconti, a nobleman who began ruling over Montisi in 1291 and was despised by everyone. For a very good reason, as he refused to let go of his position and placed all his troops in Montisi to make sure no one tried to stir any trouble, then eventually he burned down every single house and murdered almost every inhabitant.

Image by Winenews


Vineria Portofranco

natural wines & plates

A curated selection of Italian and international natural wines in a welcoming space with two lovely and knowledgeable hosts.

Image by Taverna in Montisi

Taverna in Montisi da Roberto

rustic Tuscan

Traditional dishes in a rustic and warm environment, each ingredient carefully selected by the host and Chef, Roberto

Image by l'Ombelico del Mondo

L’ombelico del Mondo

curated food & wine

A welcoming and very simpatico host will guide you through the dishes of the day, and expertly suggest what wines you should pair.



Castelmuzio is a town within the comune of Trequanda, the development of a settlement which appeared between Etruscan and Ancient Roman times. The archeological findings of a temple, dedicated to the goddess Iside, worshipped by the Etruschi, was uncovered in Castelmuzio.

As its neighbouring towns, Castelmuzio was under the control of the Republic of Siena until the castle was bought by Andrea Piccolomini, in 1470. In 1559 Castelmuzio became part of the Grand Duchy of Tuscany until Italy’s unification, in 1861, when it became a frazione of Trequanda.

Image by wikipedia


Pieve di Santo Stefano a Cennano

Image by wikipedia

A religious construction built in the Middle Ages following a Romanesque style of architecture.

Aperitivo with a view

Cross Castelmuzio’s winding streets until you reach the panoramic viewpoint found at the end of Via Gaetano Milanese, where you’ll find a series of tables and chairs free to be used by anyone. Be sure to bring a bottle of wine and something to nibble on as you enjoy an aperitivo on the beautiful terrace overlooking Val d’Orcia and Monte Amiata.

Image by The Isabella Experience


The Isabella Experience

from rustic Tuscan to upscale luxury

Choose from an agriturismo—which can be rented in its entirety too, a luxury private villa on the edge of town or a townhouse within Castelmuzio’s Medieval walls.