Information search is central in the potential tourist’s decision-making process yielding the selection of the personally most appealing tourist destinations and attractions to visit, as well as experiences to engage in. Previous research has shown diverse information search behaviors amongst tourists. A sound knowledge of this behavior is key to effective tourism marketing, helping tourism agents improve their market communication to attract valuable traveler groups. This rationale is illustrated through a segmentation study of visitors of rural wine routes in Portugal. The use of distinct information sources, before and during travel, assessed through a visitor survey in three wine routes, is the basis of a cluster analysis revealing five distinct information-seeking visitor segments. Additional comparative analysis between these segments provides important complementary insight helping both to evaluate segments and to develop corresponding destination marketing strategies.