The night before I'm due to leave the crowds of Rome behind, I am in a room full of Italian lawyers, none of whom had ever heard of Pico – my next destination – despite it being less than an hour away by car. Granted, there are many small Italian villages dotting the boot-shaped peninsula where you can slip away from the masses and enjoy an authentic and quiet lifestyle in the countryside, dotted with olive trees and grape vines. Despite its proximity to major towns and tourist attractions, however, Italy's medieval village of Pico remains a treasure to be discovered.

Pico has yet to make a list of best small towns in Italy even though it's one of the most well preserved medieval towns in the province of Lazio. In fact, I found Pico purely by chance while playing a game of travel roulette, where you spin the globe and see where your finger lands. My version had a couple stipulations. First, it had to be in Italy; and second, it had to be on the same latitude as my hometown of Cleveland, Ohio.