Maximizing theory differentiates between individuals who accept minimally sufficient purchase options and those who strive to maximize their value for money. Maximizers are less satisfied with their decisions and suffer diminished subjective well-being. We analyzed 376 questionnaires and conducted 12 interviews of working Germans to extend maximizing theory to vacations, which are more complex, experiential, and hedonic than products studied in previous research on maximizing. Path analysis of questionnaire data showed significant, negative indirect effects of maximizing on subjective well-being through aspects of the vacation decision process and subsequent vacation satisfaction. Deductive thematic analysis of interviews showed that maximizers’ time-consuming searching through alternatives created doubt and stringent expectations, thus explaining how maximizing degrades vacation satisfaction and subjective well-being. Thus, we suggest that individuals be conscious of the personal resources and expectations that they invest in vacation decisions. Furthermore, the tourism industry should emphasize inspiration and customization instead of variety.