Farming system design needs to adopt a landscape perspective in order to better respond to sustainability issues at the regional scale. Thus, we built a method at the regional scale to design agricultural land systems accounting for field characteristics and farm diversity, current farming systems and cropping systems, and the ecological processes (e.g. pollution of water bodies) at the regional scale. This method encompasses the definition of a farm typology to approach farmer's decision processes in term of cropping system choice. This farm typology is integrated within a regional bioeconomic model that produces new agricultural land systems by simulating farmers' decision processes in term of cropping system choices at plot scale, within the entire region. These new agricultural land systems are assessed with a set of indicators to provide information on their response to sustainability issues. This model coupled to the indicators are used within a scenario route to provide information on the relevance of combination of agronomic, economic, social and environmental levers to improve the contribution of agriculture to sustainable development. The method is applied in Guadeloupe for prototyping agricultural land systems that improve the response of agriculture to economic, social and environmental challenges with levers such as "agro ecological crop-gardening cropping systems", "energy crop", "changes in crop subsidies" and "availability of experienced workforce in farms". This method could be used in the Caribbean islands to help decision-makers improve the response of agriculture to sustainability challenges such as reaching food self-sufficiency, increasing employment and decreasing environmental impacts of agriculture. Coupling this approach to land use change study could provide a way of designing future sustainable islands.