Making the most out of a short-term study abroad program is vital for students who are investing in an experience they hope will benefit them personally and academically. This study explores participants' counterfactual understandings of a three-week short-term study abroad program focusing on content and English as an additional language learning for Japanese undergraduate students at a university in British Columbia, Canada. It identifies what participants wish they had known about where they were going and what they would have done if they had known that information. Qualitative methods were used to gather written narrative data from 37 participants and analyze that data for themes emerging from the participants' counterfactual reflections. Results point to six themes related to the participants' unexpected short-term study abroad experiences: food and drink, facilities, money matters, shopping, climate and geography, and community characteristics. On reflection, if the students had known more about those themes, they may have prepared differently for their trip and they might have had different experiences during the program. To prepare students to get the most out of a short-term study abroad program, pre-departure activities making use of inquiry and task-based/experiential learning are recommended.