Whale-related tourism is an increasingly popular activity which may be used to drive conservation efforts. This study explored the relationships between empathy, conservation behaviors, anthropomorphism, connectedness to nature, and experiences of whale watchers and swim-with whale tourists. Participants (n = 45) from Australia and the Kingdom of Tonga completed trait questionnaires pre-swim and then questionnaires relating to their experience at post-swim. The predictions of the dispositional empathy with nature theory were supported as empathy was associated with higher anthropomorphism, connectedness to nature, and greater intention to engage in conservation behavior. Females were also higher than males on empathy. Being close to the whales, making eye contact, and seeing calves resulted in greater enjoyment. Understanding the potential connection visitors may have during a whale encounter will enhance experience design and identify avenues to increase conservation efforts.