Students studying abroad already don’t leave home without their mobile devices—phones, MP3 players, netbooks, laptops. The potential for m-learning for these device-toting learners holds great promise that can easily be capitalized upon by the savvy teacher. Learners studying abroad who are outfitted with m-learning devices which include well-chosen Web 2.0 resources derive immediate and long range benefits. Furthermore, when organized to communicate with learners back home, the travelers help create a transnational community of practice that shares the wealth of the experiential learning. This chapter takes a tour of mobile learning technologies and techniques that enhance and extend the study abroad experience far beyond the reach of a small group fortunate enough to travel. As has long been the case with CALL (Computer Assisted Language Learning) and TELL (Technology Enhanced Language Learning), and now with MALL (Mobile Assisted Language Learning), experts note that well-chosen resources, along with carefully structured and planned activities, enhance various aspects of language acquisition and social interaction. After the literature review, this chapter considers lessons gleaned from the author’s trails, trials, and errors across a range of technologies and borders. It ends with suggestions for ways to optimize iStudyAbroad today and tomorrow.