Many discrete choice contexts in transportation deal with large choice sets, including destination, route, and vehicle choices. Model estimation with large numbers of alternatives remains computationally expensive. In the context of the multinomial logit (MNL) model, limiting the number of alternatives in estimation by simple random sampling (SRS) yields consistent parameter estimates, but estimator efficiency suffers. In the context of more general models, such as the mixed MNL, limiting the number of alternatives via SRS yields biased parameter estimates. In this paper, a new, strategic sampling scheme is introduced, which draws alternatives in proportion to updated choice-probability estimates. Since such probabilities are not known a priori, the first iteration uses SRS among all available alternatives. The sampling scheme is implemented here for a variety of simulated MNL and mixed-MNL data sets, with results suggesting that the new sampling scheme provides substantial efficiency benefits. Thanks to reductions in estimation error, parameter estimates are more accurate, on average. Moreover, in the mixed MNL case, where SRS produces biased estimates (due to violation of the independence of irrelevant alternatives property), the new sampling scheme appears to effectively eliminate such biases. Finally, it appears that only a single iteration of the new strategy (following the initialization step using SRS) is needed to deliver the strategy’s maximum efficiency gains.