Dievole's blog

Castles in Tuscany, an itinerary

In Tuscany castles may be less omnipresent than villas, but there are still plenty for the traveler who dreams of life like a royal. Imagine what this must have been like, leisurely (except in times of war!) and with brilliant food and views and service — hey, a lot like now!

The Chianti area is home to various medieval castles. There are actually five routes connecting small villages, churches and abbeys. This area is also known as that of the “Castle Roads” (strada dei castelli) and it is here that, for centuries, both Florence and Siena built villages and castles on hilltops in order to maintain control over the land. Here’s a selection of our favourites that you might write down for an itinerary of Tuscan castles on your next trip.

Castello delle Quattro Torra (Siena)

This castle is not very far from Siena and has a very interesting history. It was built at the beginning of 1300 by Cinughi family, one of the richest families of Siena at the time. Its original name was Santa Regina, in honor of the church with the same name that is located just a few hundred meters away. In 1376 it became property of the Bichi family that decided to restore the entire castle and give it a new name inspired by its four towers. It played a key role during the War of Siena in 1555 – when the entire area became part of the Granducato di Toscana ruled by the Medici family. The castle is now private property and is opened to the public only on very special occasions, but you can still visit the surrounding hilly area, the picturesque Santa Regina Church and the beautiful medieval borgo.

Castello di Brolio (Gaiole in Chianti, Siena)

photo by Mirella on Flickr

photo by Mirella on Flickr

The castle of Brolio rises in the very heart of the Chianti region and it has been part of the Ricasoli property since the 12th century. The castle stands on top of an isolated hill and its construction dates back to the Middle Ages. Due to its strategic and protective position, it has been attacked several times: during the conflict between Siena and Florence to the Spanish invasion during the fifteenth century and the bombings during the Second World War. Over the last century the castle underwent a huge restoration and rebuilding process. Brolio is now a private property but you can visit various areas of the castle and its museum with an excellent and informative guided tour, as well as the spectacular green area, full of oak and chestnut trees, vineyards and olive groves.

Castello di Gabbiano (Mercatale Val di Pesa, Florence)


Photo by Mirella on Flickr

The castle is located between Siena and Florence and is surrounded by the wonderful countryside typical of this area. It was built by the Bardi Family – one of the richest families in Florence – who also built a big cellar for the storage of their wines. At the beginning of the 15th century it was bought by the Soderini family who enlarged the entire property and transformed it into a fortified mansion. This castle was particularly loved by Michelangelo and today still welcomes artists and painters who are looking for inspiration.

Castello di Vincigliata (Fiesole)

If you are in search of the perfect day trip from Florence, head to Fiesole, a small, beautiful town just a 20 minute ride from Florence’s center, and visit the Castello di Vincigliata. For many years this castle was passed on and gambled upon among the richest families in Florence, until in 1840, a young English Lord, John  Temple Leader, decided to buy it and transformed it in a beautiful summer mansion. An area of the castle is now hosting the wide art collection of Mr. Temple Leader, with sculptures, paintings and frescoes. Another area is used for events and offers a breathtaking view of Florence. If you visit, be sure to take many pics: your instagram profile will tell you “Grazie!”

Sources: 1234