Plato visited Sicily three times upon the calls from the tyrants of Syracuse. His purpose was to obtain his political vision: to integrate politics and philosophy. The upshot was always devastating.
1st journey. In 388 B.C., Plato was invited to the court of Dionysius I. Plato soon befriended Dion, the tyrant's brother-in-law, who accepted his ideas with enthusiasm, and became his devoted student. Contrarily, Plato's contact with Dionysius proved fruitless. With great effort, and only after Dion's intervention, did Plato manage to return to Athens safe. It is said that he set up the Academy right after this experience.
2nd journey. Dionysius I died in 367 B.C., and was succeeded by his son Dionysus II, who was at first under the supervision of Dion. The latter believed that if Dionysius received the appropriate education, he could develop into a philosopher-king in conformity with Plato's model. On that thought, Plato accepted Dionysius' invitation to visit Sicily for a second time. However, Dion's political enemies had already created the conditions for his and Plato's rupture with Dionysius. The tyrant condemned Dion for conspiracy, and ousted him from Sicily, while he detained Plato in the acropolis of Syracuse. Only through the mediation of the Pythagorean Archytas of Tarentum was Dionysius convinced to set Plato free.
3rd journey. Dionysius invited Plato again in Syracuse. He insisted on meeting once more with the philosopher on the ground that he had now come to terms with philosophy, and needed his guidance. Plato set out for his third expedition in 360 B.C. This new endeavour ended in the same disappointment as the previous two. Plato's hopes were dashed to the effect of distancing himself from active politics. During the last years of his life, the philosopher gave himself to the composition of his dialogues, and teaching.