When the second generation of the web, or web 2.0, emerged around 2000, it opened up the possibility of promoting personalised but collaborative learning. A new generation of mobile context-aware technologies has now emerged, which builds on web 2.0 but goes beyond it, opening up the possibility of foregrounding authentic learning in everyday contexts. To capitalise on this new potential for educational change, it is essential to develop appropriate mobile learning designs. Drawing on Pegrum’s (2014) 3-Level Mobile Learning Framework, Burden & Kearney’s (2017) Mobile Pedagogical Framework, and Clandfield & Hadfield’s (2017) Weak & Strong Interaction Model, this paper suggests that today’s optimal mobile learning designs should involve activities where the devices, the learners, and the learning experiences are all mobile; where the three dimensions of personalisation, collaboration, and authenticity are foregrounded; and where both weak and strong interaction are present. The paper will illustrate the potential of mobile augmented reality (AR) language and literacy learning projects, most of which also incorporate elements of community building and cultural exploration. The main focus will be on recent gamified learning trails in Asia, such as the Singaporean AR Heritage Trails and the Hong Kong AR TIEs (Trails of Integrity and Ethics), where students learn collaboratively in real-world settings, while practising language, developing digital literacies and 21st century skills, building community, and exploring culture. We will consider how these gamified trails are structured to enable students to draw the greatest learning benefits from digitally supported, authentic, real-world interactions.