The collection and use of data are of increasing importance not only in virtual worlds but also for real goods. New products operationalize this principle and integrate sensors, actuators and microcomputers into analog products to enable sophisticated features such as context-awareness or connectivity with other devices. The underlying concept is being discussed as "Smart Product" and aims for the automation of activities, right up to autonomization of entire products. This article raises design specifications from existing literature and instantiates Smart Products in sailing. We discuss the application of the design specifications with sailing professionals in order to evaluate its practical value and to identify further benefits. The results affirmed that sailboats can be transformed into Smart Products by the integration of information technology. However, it also turned out that additional benefits can only be tapped by the integration of further stakeholders in a systemic perspective.