This article argues that the cruise terminal ports play a crucial role in the economic and socio-cultural sustainability of destinations, bridging the onshore tourism offered among cruise companies, global operators, and local business and infrastructures. They support the promotion of local brands and reduce congestion. The impact of crowds on the identity of coastal cities triggered the attention of academia and media, alerting for their negative impact, specifically from the Mediterranean cruises. In parallel, it raised the research interest on cruise tourism carrying capacity and ports planning the integration of cruise tourists’ flow. However, previous studies focused on the residents’ and passengers’ perception of a specific destination, neglecting the port management role. This study aims to clarify the underneath dynamics that allow sustainable cruise–land visit. Employing a qualitative case study approach, it compares data obtained from secondary sources and port executives’ structured deep interviews from two leading transit ports connected with the Mediterranean. Lisbon is amongst the most popular tourism destinations and international cruise terminals; Livorno is a gateway port to Tuscany, mainly Florence and Pisa. Despite their different patterns, in both ports of call, a strong concern with sustainability and a reduced congestion effect are observed from the management actions on promoting the local offer and on revitalizing the terminal infrastructures in order to provide comfort shopping and entertainment amenities to passengers.