The cruise line industry (CLI) provides an opportunity to rapidly improve national (and regional) economies in destinations. However, lack of planning and proper preparation by destination authorities and the cruise industry can have significant impacts on the local community, commerce, and environment. This paper identifies and quantifies near-shore challenges between the national authorities and the CLI that include port facility preparedness and the potential stresses on local infrastructure. These key parameters used to quantify the impact of the CLI on established destinations can potentially become part of the analysis, negotiation, and communication between all parties involved (government, business, and tourists) as part of the contribution to ensure sustainable CLI destinations. The Port of Havana, Cuba was selected as the study site and was compared against similar cruise line destinations around the Meso-American region (Philipsburg, Sint Maarten, Belize City, Belize, and Progreso, Mexico). The Port of Havana’s natural infrastructure and the carriage available for the incoming ship (i.e., nautical charting) appear to be adequate for welcoming increased cruise ship traffic. The main concerns are the potential toll on local resources including the impact on port traffic and the local infrastructure required to support tourists once they depart the ship.