In these days one of the most recurrent problem of the EA projects, is the elaboration of a roadmap that includes the set of initiatives, that close the gaps between an initial architecture (AS-IS) and a target architecture (TO-BE). The trouble of this task, is mostly because the choice of the transition plan that composes a roadmap, is made regardless the set of criteria and needs exposed by the organization. Based on that, the present proposal, includes the construction of a tool that facilitates the analysis and elaboration of a roadmap, whose composition is a set of transitions, chosen from the criteria established by the organization and the EA project. The choice of the number of transitions and initiatives for each one, is made through an optimization algorithm based in the criteria selected.