It’s difficult to say what captures your heart when you visit a place, but you might just fall in love with Cortona. Cortona is an artsy hill town on the Tuscan/Umbrian border. Many hill towns have been overrun by tourism, but Cortona’s year round residents maintain it’s authenticity. Francis Mayes put Cortona on the map with her book, Under the Tuscan Sun. The story of a recently divorced woman whose spontaneous purchase and of a crumbling villa in Italy, restores and revives her own broken heart. Cortona is also a favorite destination of Jordan Schlansky, Conan O’Brian’s quirky producer and Italianfile. I spent 4 days in Cortona and it left a strong impression.