As far as crop acreage choices are concerned, a consensus seems to exist among agricultural scientists and extension agents: crop rotation effects and the related constraints are major determinants of farmers’ crop choices. Crop rotation effects are inherently dynamic. They are generally ignored in multicrop models with land as an allocable input found in the literature since most of these models are developed within a static framework. The aim of this paper is twofold (i) to propose a new approach and tools for investigating dynamic crop acreage choices accounting for crop rotation benefits and constraints and (ii) to illustrate the impacts of crop rotation effects and constraints on farmers’ acreage choices through simulation examples. The models proposed in this paper are sufficiently simple for being empirically tractable either in simulation studies or in econometric and mathematical programming analyses. Our simulation results tend to show responses of the optimal dynamic acreages to simple price shocks which are much more complex than those implied by static models. They also demonstrate that farmers’ perceptions of the future economic context are crucial determinants of their acreage choices. In fact current acreage choices may appear suboptimal in a static sense but are fully consistent when dynamic effects of crop rotations are specified.