This article examines the role of colonial institutions and legacies in shaping modern-day adaptive capacity in a postcolonial urban center in the Caribbean – Georgetown, Guyana. Focusing on the Dutch and British colonial periods of governance, it shows the ways in which these colonial periods have shaped the physical and social structures of the city, and influenced many of its present-day processes and institutions, some of which are incapable of reducing the city's vulnerability to climate risks and impacts, including sea-level rise, coastal inundation, and flooding. It finds that the maintenance of critical infrastructure for building adaptive capacity such as the colonial era seawall and drainage system has been inconsistent, largely due to financial constraints. And although various international organizations have financed other large-scale hard infrastructure projects for sea and river defenses, community-based drainage projects have proven to be more successful in mitigating flood risks, illustrating the effectiveness of contemporary grassroots interventions. Beyond these, this article highlights the need for more long-term resilience and transformational measures, particularly relating to knowledge- and meaning-making, and to financing and strengthening local institutions, in order to improve the city's adaptive capacity both now and in the future.