While discussing possibilities with colleagues at my school regarding overseas educational trips for our senior students, the standard locations were considered: France, Italy, England. The usual incentives for such trips are a sense of history, the romantic images often portrayed in the media as must-see destinations, and connections to curricula. But the more we thought about the needs of our students, the more we started to consider options that offer more than just seeing—places that included doing. We were looking for activities that would help our students understand the world, balanced with the need to extend their yearlong classroom-cloistered energy. As we talked to other schools and districts, we realized that Portugal might offer even more than the typical locales, mixing history and culture with teen-friendly, risk-inspired experiences that just might provide them a new edge-ucation, and resolved to take our students there.