When people choose they often prefer similarity, rather than complementarity. This paper argues that the evaluation of a holiday destination is no exception to this tendency. The study introduces tourist–destination personality similarity (TDPS) as a concept that is distinct from perceived overall fit (POF) between tourist and destination, and examines the effects of these two concepts of congruence on vacationers’ satisfaction and recommendation behavior. Examining a sample of actual vacationers (N = 308) in a holiday resort, TDPS and POF emerged as two related, but distinct concepts: TDPS was a driver of POF, which in turn increased tourists’ satisfaction and actual recommendations of the destination. Our results confirm TDPS as a valuable tool for tourism brand managers and tourism research.