In this chapter we present and discuss the results and reflections based on our recent developments and experiences in Europe and in Asia regarding how novel educational design patterns, mobile technologies and software tools can be combined to enhance learning. We propose and recommend possible directions for the design of future educational activities and technological solutions that can support seamless learning. To the end, we discuss how the notion of seamless learning could be used to tackle some of the challenges our educational systems are facing in connection to the introduction of mobile technologies into classrooms settings, innovative educational practices and sustainability.