A fairly comprehensive range of planting choices made by maize farmers in Kenya (including discrete endogenous variables creating self-selectivity) is modelled and estimated as one system of interrelated decisions. Two-stage and three-stage probit procedures are used to handle the simultaneity and self-selectivity problems. Results showed that population pressure and agroclimatic diversity are important determinants of crop intensification and planting regimes among maize farmers and further supported the importance of focusing maize research in terms of agroclimate and socio-economic domains. Shorter maturity and efficient double and multiple cropping methods are needed to increase land productivity and intensity of labour use in areas of high population pressure and bimodal rainfall, i.e. mid-altitude zones. On the other hand, technologies that would lead to increased productivity of capital and higher response to external inputs are desired for the highlands of Kenya. Access to extension and machine services, distance to the maize plot, and time of onset of the rains were also found to significantly influence the planting strategies of maize farmers.