This paper explores the planning and management of Education Outside the Classroom (EOTC) as it relates to curriculum-based learning and teaching in schools and in this instance specifically to teaching technology education in the primary and secondary classroom. These types of experience away from the four walls of the classroom often evoke very strong memories for all of us, but frequently it is of the social context rather than the intent of the learning experience. This paper looks at Falk and Dierking’s (2000) Contextual Model of Learning and how consideration of the four over- lapping contexts of this planning model, can enhance the quality of student experiences and their learning opportunities. It will look at examples of long-term achievement and retention of student learning, the impact of an experience on student learning, and the characteristics of a successful EOTC experience.