On the highest point of Cortona, the ancient castle still stands as a reminder of stormier days- and a panoramic point for tourists. The old iron door that was once closed against invaders still stands, and among the ramparts and ruins you can see the cannon holes and other defensive mechanisms (like where they would have thrown down fire and burning oil on arriving thugs). It is called the Fortezza Medicea for the Medici family who rebuilt it, but is also referred to commonly as Fortezza Girifalco, as well.

The fortress might have Etruscan origins, but it was rebuilt in the 1200s. When Cortona was under Siena the fortress was amplified and protective walls added, but shortly after the city passed to Florence in 1411. Cortona was a very strategic place for the Florentine Republic, because of the wars with Siena and its location along the border of the Papal States.

The fortress sits on the top of the crest, its current form built by the Grand-duke Cosimo dei Medici in 1561. It has an irregular trapezoidal form with four corner bastions, each named for a saint (St. Egidio, Giusto, Santa Maria Nuova, and Margherita). There is a walkway on the ramparts that provides a very panoramic point for visitors to enjoy the views of the Tuscan countryside, sweeping out over the Val di Chiana, Mt. Amiata and Mt. Cetona, down to Lake Trasimeno.

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