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Cortona and Surroundings

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Discover Tuscany and Umbria

Villa Il Trebbio is located at the foothills of Cortona, a Tuscan town of Etruscan origin famous throughout the world for its historical and artistic beauty and good food. Take the time to visit Cortona, as it is one of the main cities of art in Tuscany, and is characterized by a unique blend of culture, history, art and nature.

Cortona is also an ideal jumping off point for discovering famous Tuscan and Umbrian cities that have great food traditions, such as Pienza, Montepulciano, Montalcino, San Gimignano, Monteriggioni, Florence, and Arezzo. There are also the beautiful sights of Lake Trasimeno and the cities of Perugia, Assisi, and Orvieto. Here are some brief suggestions of places and things to visit.



An Etruscan hilltop town that looks out over the Valdichiana valley, the city has breathtaking views that extend all the way to Lake Trasimeno and Monte Amiata. Cortona is one of the most popular destinations for tourists coming from all over the world, many of whom have fallen so in love with the city that they have moved here!

The city safeguards a rich and unique artistic heritage that includes the Tabula Cortonensis, works by Luca Signorelli, the Annunciation by Beato Angelico, and art by Gino Severini. The oldest palazzi in the historic center of town speak of the city’s history, as do the Palazzo Comunale, the Sanctuary of Santa Margherita, the Franciscan hermitage of Le Celle and the Girifalco Fortress.


Montepulciano, Pienza, Montalcino

Easily reachable from Villa il Trebbio are these true gems. Montepulciano, with its famous Piazza Grande and its cathedral, is filled with architecturally fascinating palazzi built by the great Renaissance masters. You can breathe in the air of the Middle Ages, see craftsmen’s workshops and art galleries, and above all savor the city’s real gold: Vino Nobile.

The Val d’Orcia come as a surprise, with its world-renowned landscapes. A UNESCO heritage site, it is one of the most visited places in the world, with magical views and sunsets.

Montalcino and Pienza are two pearls in the valley. They hold art treasures and a thousand-year history. Brunello di Montalcino, considered one of the most precious wines in the world, is the real king here. Pienza, meanwhile, is the city of the Popes, and filled with ancient splendors.


Perugia and Lake Trasimeno

Perugia is a journey through art, history, and traditions. It boasts one of the oldest universities and the largest university for foreigners in Italy. The city is famous for its historic center, with the ancient medieval village, but also for being the gateway to the locations dear to of St. Francis: the cities of Assisi and Gubbio are just a few kilometers from Perugia and, if you are interested in spirituality, they should not be missed.

Another magical place in the heart of Umbria is Lake Trasimeno, which is dotted with small villages, such as Castiglion del Lago, Monte del Lago and Passignano. It also has two islands that can be reached by ferry. Also worth visiting in nearby Umbria are Città della Pieve, Panicale, and Castel Rigone.


Siena and the Sienese Chianti region

Visiting Siena is like travelling through time. The life of the city is inextricably linked to the Palio, the horse race that takes place every year on July 2 and August 16, but whose energy is felt throughout the year. The “contrade” or neighborhoods are the beating heart of the Palio, and there are specific rules and codes that have been followed for centuries.

UNESCO has declared the city of the Palio a world heritage site, with its majestic Duomo, Piazza del Campo, the monumental Opera, Palazzo Salimbeni and other monuments, that should not to be missed. In the surrounding area it is possible to visit villages of rare beauty where one can enjoy wines surrounded by Chianti vineyards such as Radda, Castellina and Gaiole.


Florence and its wonders

Florence is one of Tuscany’s most important cities of art in terms of architecture, culture, trade and industry. Given its location, it can be easily reached by train or car.

Florence reached its peak between the 11th and 15th centuries, first as a free city and then later under Medici rule. During the period of the Grand Duchy of Tuscany, the city enjoyed great political and economic power. It was home to painters such as Giotto and Cimabue, Renaissance innovators such as Brunelleschi and Donatello, and universal geniuses such as Leonardo and Michelangelo. Monuments to see in Florence include the Uffizi Museum, the most prestigious art gallery in the world, Michelangelo’s sculptures, the Medici Chapel, the Baptistery with its mosaics, and the Duomo.