We report a novel educational activity designed to teach quantum mechanical tunneling to upper-division undergraduate students in the context of nanochemistry. The activity is based on a theoretical framework for analogy and is split into three parts that are linked pedagogically through the framework: classical ball-and-ramp system, tunneling involving a familiar substance (NH3 inversion), and tunneling in core/shell quantum dots. Students first begin in the classical world--the world within which they are most familiar, explore tunneling in the NH[subscript 3] inversion paradigm to gain exposure to the stark differences between classical and quantum behavior, and finally extend the concept of tunneling to the nanoscale through the examination of spectroscopic results in the literature of CdSe/ZnS core/shell quantum dots. Additionally, the activity has been assessed via a mixed-methods approach using qualitative analysis of individual student interviews (pre-and postactivity) and recordings of students' group discourse, along with small-sample statistical techniques when appropriate. Our findings suggest that students are able to successfully incorporate the language of quantum mechanical tunneling into their scientific language, and there is evidence for analogical transfer between relevant concepts within the activity.