Provided within current research extensive numerical and theoretical investigations include real maneuvering condition cases when ship-to-ship interaction phenomena play a significant role. General methodology for hydrodynamic forces and moments’ results analysis and further application within the mathematical model of marine simulators is implemented. Real conditions cases include: ship wake flow interaction with the overtaking ship; interaction between ships; speeds and transverse distance variations. Numerical investigations are carried out with the use of Computational Fluid Dynamics (CFD) methods; analysis of numerical models is completed based on the CFD codes used widely. A significant part of research is devoted to the turbulence modeling focused on flow specifics.