Pool boiling surface modification by pin fin array has demonstrated a practical but effective cooling enhancement. Whilst the main challenge is to determine the best configuration of the pin fin dimensions and positioning, it is known that the result varies among the working conditions. To obtain a more general formulation, it is utterly vital to obtain a deep understanding of the pool boiling mechanism during the phase-change process. This study aimed to analyze the role of pin fin array configuration on the pool boiling phenomenon by generating visualization and non-dimensional analysis. The results illustrated three different regimes occurring during the boiling process: natural convection, isolated bubble, and merged bubble. For all regimes, the average heat transfer performance was enhanced as the fin gap rose to 17% and 63% for circular and rectangular pin fins, respectively. Furthermore, Grashof (Gr) and Bond (Bo) numbers were calculated to quantitatively describe the effect on the bubble dynamics. From these approaches, it was found that the insulated bubble regime provides a better means of cooling by around 60% due to the better bubble dynamics.