In order to cope with several actual and future major issues like climate change, natural resources depletion, protection of biodiversity, ensuring food security, innovative agricultural systems have to be developed. These systems have to satisfy a set of objectives at the field, the farm and the territory scales and their design has to take into account explicitly the interactions between these scales (Veldkamp & Lambin, 2001). We propose a simple framework to this end and apply it to two questions in Guadeloupe: 1) the ex ante assessment of low-input innovative cropping system and their potential of adoption by heterogeneous farmers and 2) the design of new mosaics of cropping systems satisfying several sustainability goals at the territorial level and taking into account farms’ constraints.