As the impact of climate change on the agricultural sector has begun to manifest itself in its severity, adaptation planning has come under scrutiny for favoring the preservation of status-quo conditions over more substantial changes. The uptake of transformational adaptations, involving a significant re-structuring of the agricultural system, is however hindered by a lack of assessment tools capable of quantifying the effects of these often more complex, far-reaching, and unprecedented changes. Agent-based models can simulate decision processes and multi-level feedbacks between system components and may therefore illustrate how transformational adaptations emerge and help identify cases where their implementation is necessary and desirable. We explore this modelling potential and aim to quantify (1) how climate change, farmer behavior and water policies may influence strategic adaptation decision-making at the farm-level, (2) the extent to which implemented adaptations represent transformations, and (3) their impact on farm structure and wider socio-ecological change. We investigate these aims through a case study of crop farming systems in the drought-prone historical region of Romagna (NE Italy), integrating insight from stakeholder interviews, local reports, spatially-explicit biophysical data and behavioral theory in the construction of an agent-based model. Results show that, on average, more than half of all implemented adaptations are transformations, thereby requiring important social and financial investments from farmers. The number of implemented transformations is highest in scenarios where drought risk perception among farmers is more widespread, notably in scenarios simulating drier climates, more adaptive behaviors and policies promoting greater water use efficiency. Under higher drought risk perception, farmers are motivated to explore a broader set of adaptations, including those outside of the trajectory determined by their farming strategy. This process particularly favors the implementation of transformational increases in farm size and irrigated area, eventually stimulating farmers to adopt an expansionist strategy. Regionally, these adaptations lead to the smallest decline in agricultural extent with fewest, yet highest profit-earning farmers, largely exacerbating presently occurring trends. Under policy scenarios simulating increased irrigation availability, fewer farmers initially experience drought and therefore perceive a drought risk. Consequently, fewer farmers undertake transformational adaptations and switch from a contractive to an expansive strategy, culminating in a relatively smaller and less profitable agricultural extent despite a larger farmer population. As transformative changes to farming strategy trigger farmers to engage in new path-dependencies, aims of water policies may therefore rebound into unintended effects, emphasizing the importance of accounting for transformational perspectives.