The Castle of Pierle, near Lake Trasimeno to the south of Cortona, already existed in the 10th century. It was the property of the marquises of Saint Mount Maria Tiberina. In 1428 there is a contract of sale by the Republic of Florence and payment of 1200 gold florins when it became free of Cortona. However that wasn't enough to save the Rocca, and it was voluntarily destroyed by the Grand Duke so that outlaws would not take refuge there.
(a) The Florentine ruling class wanted to portray the huge domain of Tuscany as ancient Etruria, and to trace all its most famous towns right back to the time immediately following Noah's Flood. They wanted official recognition for them as a Grand Duchy, to obtain the title of Grand Duke for Cosimo. This was granted by Pope Pius V in 1570.
(b) The Cortonese ruling class wanted to portray the city as the oldest and most noble in Tuscany, and to suggest that its local government arose from the Etruscan lucumonia and had been perpetuated in the medieval Comune. Hence they could argue for a share in the citizen government, after their rivals, the Florentine Lords, had taken control of the town.
The 17th-century Guide of Giacomo Lauro, reworked from writings of the notorious forger Annio of Viterbo (1432-1502), which draws on many ancient writers, tells that 108 years after the Flood Noah, navigating from the mouth of the Tiber across the paglia entered the Valdichiana and, liking this place better than anywhere else in Italy because it was so fertile, stopped and dwelt there for thirty years.
Among his descendants a son named Crano came to the hilltop and, liking the high position, the fine countryside and the calm air, built the city of Cortona on it in the year 273 after the Flood. Stefano (Greek historian, c.AD 539-545) calls this the third city of Italy constructed after the Flood, and the original capital of the Turreni. Noah, approving of Crano's work, named him Corito, i.e. King, and heir to the Kingdom.
Crano, taking this title, built a palace tower atop the hill. Its remains are still at Torremozza. Crano's kingdom was called Turrenia because Noah's descendants built cities with high towers. That was the original name of Tuscany, and its inhabitants were called Turreni. But being descended from Noah, who was saved from the waters (Latin, "ab imbribus"), some were also called Imbri or (commonly) Umbri.
Dardanus, a descendant of Crano, after local disputes fled to Samothrace, then to Phrygia and at last to Lydia, and founded there the city of Troy. From Troy some descendants of Dardano, still Greek, returned to live in Turrenia (i.e. Toscana), and were the Etruscans. Among them were Ulysses and Pythagoras.
Aristotle (4th century BC) and his contemporary Theopompus report older traditions that Ulysses emigrated to Italy after his return to Ithaca. According to them he came to Etruria, to a city which Theopompus calls Curtonaia, and they locate his tomb nearby. In Etruria (where he is esteemed) Ulysses was called Nanos, 'the Wanderer', and his tomb was said to be at "Monte Perge" near modern Pergo. According to Virgil (Aeneid III and VII) Aeneas, a descendant of Dardano, fled the destruction of Troy and came to Latium (Lazio) where his descendants founded Rome. Hence Cortona had given rise first to Troy, and then to Rome.
The story that Pythagoras lived at Cortona, died and was buried there (the "Tanella di Pitagora") was a confusion between Cortona and Crotona in southern Italy.
The prevailing character of Cortona’s architecture is medieval with steep narrow streets situated on a hillside (altitude 600 metres), embracing a view of the whole of the Valdichiana. From the Piazza Garibaldi (still referred to by the local population by its older name, Piazza Carbonaia) is a fine prospect of Lago Trasimeno, scene of Hannibal's ambush of the Roman army in 217 BC (Battle of Lake Trasimene). Parts of the Etruscan city wall can still be seen today as the basis of the present wall. The main street, via Nazionale, is the only street in the town with no gradient, and is still usually referred to by locals by its older name of Ruga Piana, or "level street".
Inside the Palazzo Casali is the Museo dell'Accademia Etrusca that displays items from Etruscan, Roman, and Egyptian civilizations, as well as art and artefacts from the Medieval and Renaissance eras. The distinguished Etruscan Academy Museum had its foundation in 1727 with the collections and library of Onofrio Baldelli. Among its most famous ancient artefacts is the bronze lampadario or Etruscan hanging lamp, found at Fratta near Cortona in 1840 and then acquired by the Academy for the large sum of 1600 Florentine scudi. Its iconography includes (under the 18 burners) alternating figures of Silenus playing panpipes or double flutes, and of sirens or harpies. Within zones representing waves, dolphins and fiercer sea-creatures is a gorgon-like face with protruding tongue. Between each burner is a modelled horned head of Achelous. It is supposed that the lampadario derived from some important north Etruscan religious shrine of around the second half of the fourth century BC. A later (2nd century BC) inscription shows it was rededicated for votive purposes (tinscvil) by the Musni family at that time. The Museum contains several other important Etruscan bronzes.
Etruscan chamber-tombs nearby include the 'Tanella di Pitagora' (halfway up the hill from Camucia), two at the foot of the hillside at Il Sodo, and a complex in Camucia itself. Il Sodo I contains pitch-roofed chambers of slab construction with an inscription, and can be visited. Il Sodo II contained a large stone-stepped altar platform with carved sphinxes devouring warriors.
The town's chief artistic treasures are two panels by Fra Angelico in the Diocesan Museum, an Annunciation and a Madonna and Child with Saints. A third surviving work by the same artist is the fresco above the entrance to the church of San Domenico, likewise painted during his stay at Cortona in 1436. , The Diocesan Museum houses also a group of work by Giuseppe Maria Crespi, known as Lo Spagnuolo, called Ecstasy of St. Margaret. The Academy Museum includes the very well-known painting Maternità of 1916 by the Cortonese artist Gino Severini. There are also examples of the works of Pietro Berrettini (1596-1669), called Pietro da Cortona, pupil of Andrea Commodi.
Santa Maria Nuova
Santa Maria Nuova, built by Giorgio Vasari in 1554, is a church of square ground-plan. The Renaissance took hold anew of the ideal of the centralised ground-plan for church-building. This building is of extreme interest for its ground-plan of a Greek cross and surmounted by a main cupola which was only finished during the 17th century, a primary example of such a centralised design. Inside rise the four mighty columns on which the lantern of the cupola is supported. At the sides the four arms of the cross branch out covered with barrel-vaults, while four small cupolas arise in the spaces of the angles. Among the works of art are the Nativity by Alessandro Allori, San Carlo Borromeo che porta la Comunione agli appestati by Baccio Ciarpi, and the Annunciation dell'Empoli. The church is unfortunately not in very good condition, and is not open for sightseeing or inspection.
Santa Maria delle Grazie
Only a few hundred meters away stands the church of "Santa Maria delle Grazie". It was built in 1484-1515 by Francesco di Giorgio Martini (1439-1502) in connection with an alleged miracle-performing image of the Blessed Virgin Mary, the "Madonna del Calcinaio". This image was originally painted on the timbers of a lime-vat, a calcinaio, hence the name.
In cases like this, where the strength of the Renaissance ideal of centralized building-design is applied to a nave-construction, the eastern part of the building was generally developed into a centralized form, that would then be crowned with a large cupola, foreshadowing the cathedral at Florence. Externally the church does not appear especially remarkable, but it has been very beautifully restored within. It has unusually high arches. Here also can be discerned the distinguishing marks of Renaissance architecture: clear, geometrical forms, the combination of rectilinear forms with bowed shapes and circles, classicizing gabled windows, the colouring of the plain surface, which is maintained entirely in white.
(Text from German Wikipedia)