Ecotourism from its genesis and founding theories has been set out to conserve and preserve the environment through sustainable operation that includes surrounding communities in efforts to reduce their poverty levels. Over the years ecotourism has been hypothesized to have departed from this ideal with several researchers, through social, qualitative analyses, have said that these non-sustainable ecotourism operations are simply due to poor management. This work sought to test this central hypothesis as a first approach to quantitatively linking ecotourism activities to management with surface water quality as the key indicator of sustainable ecotourism as a complex system through systems thinking. This pilot work was done by the use of two study sites in the Caribbean: Iwokrama, Guyana and Greencastle, Jamaica. From General Systems Theory, before systems dynamics can be applied there is a need to first observe components of the system in a reductionist view. This approach had to be taken also since the required data inputs for the systems approach were not available, as is the norm throughout the Caribbean. Thus by creating simple, easy-touse and transferrable sustainability indicator based reductionist-type assessment tools relevant data on ecotourism activities, management and water quality can be obtained in the future and acts as a start to understanding the true systems dynamics among these three entities. The creation of these quantitative reductionist tools utilized social surveying onsite, target plots, sustainability indicators and Social Network Analysis. Tools created were tested through what-if scenarios, with sensitivity analyses, and determined to be able to respond to societal, environmental and economic changes. The basic findings of these reductionist tools were used to establish and initial pathway for quantification inclusive of a framework in STELLA® for the numerical linking of ecotourism management, water quality and sustainability indicators in the Caribbean. This work also established water quality baselines for both study sites through in situ water sampling and testing and further ex situ analysis. As an indirect systems approach to linking sustainable development and the Caribbean, an audit of the Caribbean’s primary and secondary school’s system was conducted and recommendations suggested for the infusion of sustainability into formal education both during and after the United Nations Decade for Education for Sustainable Development (2005-2014).