I first met Anna Piperato more than a decade ago, not long after she had given up teaching at High Point University to pursue her dream of living in Italy. She has a PhD in Art History, her dissertation is on Saint Catherine of Siena, and there seems to be little that she doesn’t know about Italian Medieval and Renaissance art and history.

Today she is living her dream. Now an independent tour guide, she has worked for Rick Steves and still handles his Tuscan Hill Towns tours. But she loves Siena best of all and is also an active and fervent member of the Lupa Contrada and all things dealing with the Siena Palio. She is a great guide, as well as a wonderful person and delightful raconteur. I knew that we couldn’t do justice to seeing and touring Siena without her expert guidance. We were not disappointed.

After getting us to Siena and talking us through the not easy Siena parking situation (Siena is a walled city with very limited car access so you have to park in one of their massive car parks outside the city and walk in), we met up with Anna at Siena’s famous Campo, the town’s main piazza. As she walked us to our lunch venue, she tried to connect us to the history of the city while saving the main tour until after lunch.

Rosticcieria Vitti, a small relatively new restaurant is tucked away in the tiny Piazza Vitti. It was perfect for a reunion with Anna and the restaurant served a wonderful array of antipasti, bruschetta, and crostini followed by a variety of pasta dishes. The meal finished with some lovely desserts, including cantucci with Vin Santo.

Anna then took us to her to new apartment just a couple blocks from the restaurant. She and her family were able to renovate an apartment in a centuries old building, within the confines of the Lupa contrada. Anna did an incredible job working with the architect to build a modern, up to date apartment while keeping in mind the history and provenance of the building. We all loved seeing her new home and knowing she will be living in these beautiful surroundings.

Siena’s history is long, complicated, and interesting, but thanks to losing out to Florence after the Black Plague in the 14th century it remained a vibrant and important city but no longer sought to compete to dominate Tuscany. In my opinion, that is the reason that the city is so much more lovely to visit than Florence which today is overrun with hordes of tourists. Look up Anna if you are ever thinking about visiting the Siena; she will make it worth your while.