Interplanetary multiple gravity assist (MGA) trajectory optimization has long been a field of interest to space scientists and engineers. Gravity assist maneuvers alter a spacecraft's velocity vector and potentially allow spacecraft to achieve changes in velocity which would otherwise be unfeasible given our current technological limitations. Unfortunately, designing MGA trajectories is difficult and in order to find good solutions, deep space maneuvers (DSM) are often required which further increase the complexity of the problem. In addition, despite the active research in the field over the last 50 years, software for MGA trajectory optimization is scarce. A few good commercial, and even fewer open-source, options exist, but a majority of quality software remains proprietary. The intent of this thesis is twofold. The first part of this work explores the realm of global optimization applied to multiple gravity assist trajectories with deep space maneuvers (MGA-DSM). With the constant influx of new global optimization algorithms and heuristics being developed in the global optimization community, this work aims to be a high level optimization approach which makes use of those algorithms instead of trying to be one itself. Central to this approach is PaGMO, which is the open-source Parallel Multiobjective Global Optimizer created by ESA's Advanced Concepts Team (ACT). PaGMO is an implementation of the Island Model Paradigm which allows the parallelization of different global optimizers. The second part of this work introduces the IGATO software which improves PaGMO by complementing it with dynamic restart capabilities, a pruning algorithm which learns over time, subdomain decomposition, and other techniques to create a powerful optimization tool. IGATO aims to be an open-source platform independent C++ application with a robust graphical user interface (GUI). The application is equipped with 2D plotting and simulations, real time Porkchop Plot generation, and other useful features for analyzing various problems. The optimizer is tested on several challenging MGA-DSM problems and performs well: consistently performing as well or better than PaGMO on its own.