The Italian coast has about 700 ports, which are different in typology, dimension, role, and ownership. Historically, this has led to the significant fragmentation of governance and space and a lack of cooperation that ports and cities still experience today. Among all ports, small and medium-sized ports (SMPs), such as marinas, small touristic harbors, and moorings, are the most affected. Unlike the main ports, where spatial and strategic regulation planning fall under the port authority’s responsibilities, SMPs are a combination of public and private management and are, therefore, excluded from national and regional planning and larger strategies. Improving SMPs’ cooperation at the regional level can drive more effective sustainable management among related activities (tourism and the fishing sector) and reduce pressures on the land–sea interaction (LSI). In filling the gaps, this article challenges the existing legal framework, planning tools, approaches, and initiatives and may pave the way to establishing a better-integrated national governance for SMPs. In conclusion, this paper identifies two main opportunities that can support the steady establishment of governance and the systematic harmonized development of these SMPs. The first one is offered by maritime spatial planning (MSP) as a strategic and legal tool whereby SMPs are recognized and, if financially supported, could find incentives and measures for their development. The second one is through European projects, programs, and initiatives such as Framesport as drivers in establishing a common ground among public and private interests and as a cooperation engine at a local scale.