In this proposal we present the results of a project developed in teacher education programs at the University of Minho, Braga, Portugal. The main goal of the research was to test the importance of providing technological-rich experiences in education programs as a strategy to promote the integration of technologies in the curriculum As educators in a public higher education institution we assume that the failure of ICT integration in Portuguese schools is due to a lack of teacher training in technology-supported pedagogy. Having as theoretical framework the TPACK model developed by Koehler and Mishra (2009), we present and discuss the results of sixteen case studies enrolling 203 undergraduates and 117 in service teachers where different Web 2.0 tools were explored in different formal and informal contexts and with diverse pedagogical goals: to build e-portfolios, to enhance cooperation and collaboration among peers, to develop skills in searching, organizing and sharing web resources, to facilitate interaction and communication in online learning communities or to create digital resources. Results are presented and discussed in order to infer a set of guidelines for the design of teacher education programs regarding the integration of ICT in the classroom.