Web exploration through trial and error is one of the essential factors in advanced intellectual activities, such as group work in project-based learning (PBL) and research work. Precisely grasping search results and their circumstances, i.e., search contexts, is quite important in enabling such intellectual activities to be successfully carried out. However, such grasping is quite difficult for unskilled learners since skills for such exploration should be acquired through practical experiences. Furthermore, although novices particularly need to obtain experience through meaningful trial and error, they tend to become immersed only in a part of Web exploration, such as query creation. This research was aimed at developing novel support for facilitating experiences through meaningful trial and error by reducing the extra hurdles to Web exploration. Specifically, this research focused on three main phases in Web exploration: contriving search queries, scrutinizing promising Web pages, and organizing exploration deliverables. In this paper, we mainly describe a support framework and proposed methods based on these phases.