In this paper we propose a systematic strategy for migrating crosscutting concerns in existing object-oriented systems to aspect-oriented programming solutions. The proposed strategy consists of four steps: mining, exploration, documentation and refactoring of crosscutting concerns. We discuss in detail a new approach to refactoring to aspect-oriented programming that is fully integrated with our strategy, and apply the whole strategy to an object-oriented system, namely the JHotDraw framework. Moreover, we present a method to semi-automatically perform the aspect-introducing refactorings based on identified crosscutting concern sorts which is supported by a prototype tool called SAIR. We perform an exploratory case study in which we apply this tool on the same object-oriented system and compare its results with the results of manual migration in order to assess the feasibility of automated aspect refactoring. Both the refactoring tool SAIR and the results of the manual migration are made available as open-source, the latter providing the largest aspect-introducing refactoring available to date. We report on our experiences with conducting both case studies and reflect on the success and challenges of the migration process.