Travel through olive groves and vineyards to explore hill towns such as : Castiglione del Lago and Cortona. Castiglione is a fortified city on a small promontory on the west side of Lake Trasimeno. The city is still completely surrounded by the city wall with its original three gates. It is divided into two parts, the inhabited part that goes toward the land and that part which goes toward the lake which has only the Duke’s Palace and a large medieval fortress that owes its name to the city. Lake Trasimeno is Italy’s fourth largest lake , and was the site of one of the largest massacres of the Roman army at the hands of Hannibal. The valley is now a quiet, peaceful place, tucked away on the border between Tuscany and Umbria. Continue your journey to Cortona. It is the best known and world famous hill-town of Tuscany and deservedly so, since Cortona is as old as Troy, and this is proven by recent exciting archaeological discoveries, and by the numerous finds now displayed in the newly restored Archaeological Museum The city was a major seat of power during the medieval period, able to hold its own against larger towns like Siena and Arezzo; its decline was followed the defeat by Naples in 1409 after which it was sold to Florence and lost its autonomy.It 'snarrow streets and alleyways give you the impression of how it must have been in these small isolated towns in the medieval period, and you’ll realize how much history a little town can contain