This work investigates the optimization and design of a N-capacitor resonant Dickson converter for capacitive wireless power transfer (WPT). A testbed that allows for the analysis of parasitic and coupling capacitances within a N-capacitor plate setup is presented. A 4-capacitor resonant Dickson converter is tested and three setups that vary plate design and distances and thereby parasitic and coupling capacitances are tested and shown with comparisons to ANSYS simulations. This work looks to systematically characterize parasitic and coupling capacitances and create a model to maximize power transfer, enabling the design of higher power density capacitive WPT systems.