Preparing teacher candidates for their roles in 21st century schools calls for direct experiences with inquisitive, linguistically diverse, and often technologically savvy students across global and economic contexts. This article presents the lessons learned from a practicum experience during a semester abroad in Italy, where faculty, teacher candidates, and students engaged in educational and cultural collaboration. After collaborating with a school in Siena, Italy, the author and nine teacher candidates created a practicum lesson using technology to teach 8th grade students social studies subjects. The class was broken into small-groups of 3-4 students to a teacher candidate. Each group received three or four letters of the alphabet. Students would select one letter and brainstorm terms related to history/politics/geography associated with that letter using images that were displayed on a smartboard. The author describes the barriers, such as language, and the findings that came from the lesson.