Since 2001, classroom and pre-service teachers, along with high school and university students from Poland, Romania, Slovakia, Germany, Lithuania, Ukraine and the United States, have participated in an international workshop that focuses on preparing students and teachers for life in an increasingly interconnected world. These intercultural exchange projects are facilitated by an organization that originated in Poland, called Expedition Inside Culture, that focuses on tolerance building and democratic education through onsite study of a local region or area. For the past six years these sites have been in Eastern Europe, but they could just as likely have been in a corner of the United States, such as an Arizona town, or a neighborhood in urban Chicago. The chosen region needs to have been occupied at one time or another by various cultural groups. It should also have artifacts or evidence of the presence of those groups over time. In the authors' case, the locations are often the site of conflicting interpretations of history. These contested histories become points of deliberation central to the tolerance and democratic education goals of the experience as participants move through the five steps of their process. In this article, the authors describe an expedition project wherein they work to chronicle the learning process and to capture the dynamic nature of expeditionary learning and its impact on participants. Various technological tools have helped them to chronicle the experience, while amplifying the process in which the expeditionary learning activity evolves. (Contains 5 notes.)