This paper investigates the contributions of an intensive educational workshop to advance students’ understanding and skills for collaborative, scenario-based landscape planning. The research design involves a case study workshop with thirty international students and several regional experts as well as a multi-stage, in-process evaluation. The workshop resulted in six different alternative futures for the region of Cagliari, Italy, and a seventh combined version that was considered best by regional reviewers. The students’ learning evaluation showed substantial advances in their relevant understanding and skills. Key aspects of the workshop pedagogy and the evaluation are discussed, and recommendations for future applications presented.