Take all the time to get to know the town, find its stores and amenities as described here. This itinerary is wonderfully laidback, we don't suggest that you do too much each day, but rather return often to your temporary home in Cortona to simply sit in piazza Garibaldi and take in the view.
The best place to start touring the town is from piazza della Repubblica and piazza Signorelli. Until the 13th century, these two squares were in fact one space and also the site of an ancient Etruscan-Roman forum. Both are framed by medieval buildings and shops.
The Palazzo Comunale (Town Hall)with its impressive stairway and the giant clock tower, sits at the southern part of piazza della Repubblica. Take the opportunity to visit the Museo dell’Accademia Etrusca, Fra Angelico’s panels in the Museo Diocesano, the Medieval Church of San Francesco and the Church of Santa Maria Nuova, built by Giorgio Vasari. Of course, enjoy piazza Garibaldi where you can see Lake Trasimeno in the distance.
If you're in the mood for a walk, your next stop could be the Girifalco Fortress, also known as the Medici Fortress because it was restored and modified in 1561 by Grand Duke Cosimo I de 'Medici. Located at the highest point of the city (about 1km from piazza della Repubblica) it hosts many events and festivals such as Cortona on the Move: the international exhibition of contemporary photography which is held every year from July to September. From the top of the tower, you can enjoy a breath-taking view of Cortona and the entire Valdichiana.