One of the most important and promising application of the IoT technologies is in the interaction of “mobile” entities, like cars and trucks, with “static” infrastructures in which they are immersed and from which they depend, like motorways, parking sites, city facilities. This type of application is generally named “vehicle-to-infrastructure” communication. This paper describes the research outcomes of the Yacht Single Window (YSW) project that applied this paradigm to a new and different use case for the IoT: enabling the “vessel-to-infrastructure” communication in order to exploit the IoT technologies for the benefits of the leisure boats and yachts security, safety and improved connection.