Small Island Economies (SIE) are particularly vulnerable to external damage and have therefore been placed high on the international political agenda (IPCC, 2007, 2014). The damages of global changes, and singularly climate change in these areas, may heavily impact the agricultural sector. Combined with the perverse effects of intensive production methods, prevalent in the conventional agricultural production model, the consequences on agroecosystems are now dramatic in terms of environmental impacts and degradation of soil production conditions in particular. It is therefore urgent to change current agricultural trends towards agroecological production patterns, that are more respectful of major biogeochemical cycles. This agroecological transition requires specific tools to be designed and piloted. The Theory of Viability, offers a theoretical base and original prerequisites to address this challenge by allowing simultaneous consideration of economic and agronomic dimensions. After presenting the foundations of the Theory of Viability, we propose a dynamic model of the sequence of agricultural productions and practices that can be implemented in the long term to restore soil quality while respecting a set of agronomic and economic constraints. The paths to soil restoration vary, depending on agronomic and economic constraints, the time available for restoration, the initial soil conditions, and investment capacities. Economic valuation of the minimum cost of restoration shows that the agroecological transition may be costly and that farmers can have difficulty meeting the costs, thus raising the question of how the cost of agroecological transition is to be shared.