Nature-based tourism has surged in recent years with the desire for up-close interactions and “connections” with wild animals. The conservation value, animal welfare considerations, visitor satisfaction, and profitability of wildlife tourism are often in direct conflict with trade-offs commonly accepted. In this paper, we reviewed more than four decades of literature on the deleterious behaviors and risks documented during close tourist and other recreational interactions between humans and free-ranging dolphins and encounters between humans and lone, sociable dolphins. Our compilation provides a geographical, chronological, and qualitative overview of these encounters, reviews both humans' and dolphins' deleterious behaviors during interspecific interactions and summarizes the main risks to both humans and dolphins during close encounters. Based on this review, we outline and discuss how both animal welfare and human safety should be managed such that these activities are sustainable; the demand for personal wildlife experiences continues to grow at an alarming rate and the economic pressures placed on wild animal populations run the risk of damaging the very environmental assets that support this industry if they cannot be managed effectively.