Cortona The charming hilltop town of Cortona, where Under the Tuscan Sun was filmed Shopping in Cortona is a dream! Cortona! Shop ’til you drop! Window shopping is like candy for the eyes! Beautiful colors, luxurious leather handbags and OH….the shoes! Wine tasting is a lovely way to stop and take a break in between shopping and lunching in Cortona The ladies enjoy a casual tasting with the locals at a lovely Cantina The lovely spot on the hill, where Under The Tuscany Sun was filmed Frances Mayes’ beloved Bramasole!