Sound transmission loss (STL), an essential index for assessing the sound insulation performance of composite laminated structures, typically relies on experimental methods to measure. The soundbox method (SBM), a straightforward technique for measuring the STL, is sensitive to microphones’ positions. Within the framework of the Chebyshev-Ritz method, a semi-analytical vibro-acoustic model extended to composite laminated panels with viscoelastic damping (VED) is proposed for the first time. Based on the developed simplified layer-wise theory, the panel is modeled using three layers: the top face layer, the VED layer, and the bottom face layer. A closed cavity is added to the model as the soundbox enclosure used in actual measurements. By employing the Hamilton's principle, the governing equation for the coupling system is derived, and the vibration and internal acoustic responses of the coupling system are calculated. A discretization strategy is introduced to address the frequency-dependent properties of the VED layer, avoiding the need to reconstruct the stiffness matrix at each frequency. To obtain the STL of the panel, sound pressures at external measurement points are calculated based on the Rayleigh integral. The proposed model is validated against numerical results from finite element analyses. The influences of the microphone position inside and outside the cavity on the measured STL are studied. Furthermore, parametric studies over the microphones' positions are performed to enhance the SBM-based evaluation of the composite panel's sound insulation performance. The optimal locations for two internal microphones and one external microphone are recommended. Finally, experimental studies are carried out to guide the implementation of the SBM.