After the European Environmental Noise Directive prescribed noise maps and action plans, wide scientific literature and a consistent number of mitigation strategies emerged for road, railway, airport, and industrial noise. Unfortunately, very little attention has been paid to the noise produced by ports in their surroundings, even though there could be many areas affected by it. At present, more attention seems to be paid to noise produced underwater, mostly for military and security reasons and for its interference with wildlife, rather than airborne noise and its influence on human health. In the framework of a project aiming to shed more light on a topic so far under-investigated, this paper presents an acoustical characterization of different small vessels at various speeds that move around on a daily basis in every type of port, produced by means of short- and long-term measurements. The new information acquired was used to produce a map of noise generated by vessels moving in Livorno’s canals, which branch off in a densely inhabited area. The simulations were validated using long-term measurement. The number of citizens exposed was also estimated and used to calculate the number of highly annoyed people according to the recent curve for road traffic noise proposed by Guski et al. In order to prevent citizen exposure to noise and possible complaints about small boats, different scenarios and possible future situations such as various vessel speeds, limited flow, restricted areas for some categories, or new residential areas were studied.