Multidisciplinary courses are being developed at a number of US colleges and universities to highlight the connections between the rise or fall of world civilizations and the sustainable or unsustainable uses of soil and water resources. The content presented in these courses is complex because it includes concepts from disciplines as varied as geology, soil science, politics, economics, history, and anthropology. The learning goals for the courses include developing skills in the critical analysis of complex “real-world” problems for which there is often no simple or correct solution. Didactic materials for such courses are limited. Field trips to sites around the world that present some of the issues covered in the course would be ideal, but are logistically challenging. We considered that a series of virtual field trips (VFTs) to sites around the world would allow us to present students with complicated real-world situations, with which to practice critical analysis skills. The VFTs envisaged are neither tutorials nor field/lab exercises. Rather, they are meant to be complex, multi-faceted representations of a past or current civilization and how it affects or is affected by its environment. We expect that the students will use the VFTs to explore the relationships between physical geography and culture and how the decisions or actions of a civilization impact natural resources and the environment and thus affect its fate. A goal of the VFTs is that through consideration of their experiences, students arrive at novel associations that lead to dynamic in-class dialogue about the material presented and a deeper understanding of the intricacies of the situation in the field. This article describes the process of assembling a VFT, and analyzes the technological and didactic choices the process requires. Our experience with a pilot VFT suggests that no single medium (i.e., video clips, interactive maps, animation sequences, etc.) is comprehensive enough to meet the course learning goals. Thus, a web-based, open architecture format was selected for the VFTs because of its simplicity, flexibility and extensibility. Each medium was selected for its ability to support the course learning goals. The learning process was mediated by the VFT text, questions for thought, and in-class discussions. Preliminary results with the pilot VFT are encouraging.