The emergence of the Internet of Things (IoT) has brought more challenges for designers to fully understand networked objects and develop pleasurable user experiences (UXs). Due to the radical change of products when they are connected, traditional experience design theories may not be applicable in this new context. Based on two well-established UX design theories, this paper presents a survey study that investigated the pleasurability of IoT devices by comparing a representative IoT device (i.e., the smartwatch) and its conventional form (i.e., the wristwatch). An online questionnaire was deployed to gather feedback from parallel wristwatch and smartwatch users. Their experiences using both types of watches were quantitatively and qualitatively compared by data analysis. The results highlighted the differences in UXs between smartwatches and wristwatches in three types of pleasure and five psychological needs. The study revealed design opportunities to improve the pleasurability of smartwatches and provides novel design insights informing the development of pleasurable UXs for future IoT devices.