We propose an augmented Web space and its query language to support geographical querying and sequential plan creation utilizing a digital city that is a city-based information space on the Internet. The augmented Web space involves a new approach to integrate the World Wide Web (WWW) and a geographic information system (GIS). The augmented Web space consists of home pages (HP), hyperlinks, and generic links that represent geographical relations between HPs. The generic links are created dynamically using geographical evaluation functions included in a user's search query each time one is issued. A query also includes a path expression showing how to navigate the HPs, hyperlinks, and generic links. Since the path expression is an extended regular expression, we can describe an arbitrary sequence of users' search actions for navigating the augmented Web space. We have applied the proposed augmented Web space to Digital City Kyoto, a city information service system that is accessed through a 3D walk-through implementation and a map-based interface. Each time a user's query is issued through the 3D and 2D interfaces, Digital City Kyoto creates an augmented Web space, and navigates the Web information space based on the path expression in the query.