Advances in information technology and telecommunications, together with ever-growing amounts of data, offer opportunities for transportation companies to improve the quality of the service that they provide to their customers. This paper compares two methods motivated by the opportunity that the availability of data and technology gives to improve on current practice. In particular, the two solution approaches are explored in the context of a dynamic and stochastic routing problem in which a single, uncapacitated vehicle serves a set of known customers locations. One approach, sample-scenario planning, offers the potential for higher-quality solutions, but at the expense of greater computational effort. On the other hand, anticipatory insertion offers reduced computation and increased managerial ease, but with the potential for reduced solution quality due to restrictions on solution structure. Our results show that anticipatory insertion can often match the quality of sample-scenario planning, particularly when the degree of dynamism is low.