This study focuses on the school–work connection from the perspective of curriculum design. The aim was to uncover considerations underpinning the design of learning environments in vocational education. The research took place in the Netherlands. A focus group methodology was chosen to elicit designers’ considerations, which generally remain largely implicit. These considerations concern the designable elements of learning environments: epistemic, spatial, temporal, and social elements. Design considerations were uncovered at each of the aggregation levels of a curriculum. At the macro-level, considerations referred to the connectivity between the contexts of school and work. Based on these considerations, different designs were chosen along the school–work continuum. At the meso-level, another continuum was found: the complexity in terms of practices involved in the learning environment. At the micro-level, concrete design considerations were revealed that designers take into account to strengthen the school–work connection. Thus, design considerations at three levels were made explicit. Moreover, the need for alignment between the designable elements and the curriculum levels became more apparent, leading to a deeper understanding of curriculum design for vocational education. This paper adds understanding of ways to strengthen the school–work connection and design future-proof vocational curricula.