Creating effective sightseeing trip plans requires consideration of both positive factors, such as travelers’ preferences and the type of experience they want, and negative factors, such as travel time and travel costs. However, it is difficult for travelers to create completely satisfactory trip plans. Additionally, although it is easy to outsource trip planning to a travel agency or use an existing travel tour, the resultant plans often cost extra or are unsatisfactory. The purpose of this research was to facilitate the creation of highly satisfying sightseeing trip plans that meet the needs of travelers. In this study, a database was created of sightseeing trip plans that included positive and negative factors and had relatively high satisfaction levels. A sightseeing trip plan search service is proposed that allows users to search for sightseeing trip plans that meet their needs. To confirm the effectiveness of the proposed service, a web-based system was built that allows users to view 72 sightseeing trip plans created by students at Yamato University in Osaka and Iwate Prefectural University in Iwate, Japan. A database system was then constructed that allows users to input and search for trip plans. This paper provides an overview of these systems, evaluates the effectiveness of the proposed service, and highlights future issues to consider in fully implementing a search service for sightseeing trip plans.