Crop rotation effects and constraints are major determinants of farmers’ crop choices. Crop rotations are also keystone elements of most environmentally friendly cropping systems. The aim of this paper is twofold. First, it proposes simple tools for investigating optimal dynamic crop acreage choices accounting for crop rotation effects and constraints in an uncertain context. Second, it illustrates the impacts of crop rotation effects and constraints on farmers’ acreage choices through simple simulation examples. The proposed models are sufficiently simple for being empirically tractable either in simulation studies or in econometric analyses.