This paper presents an approach to address the complex scheduling problem faced by sales representatives. Many scheduling and routing problems have been explored before in research but real-life applications often feature complex constraints and requirements. The problem we propose is a variant of the travelling salesman problem, in which customers must be visited multiple times over a long planning period at different intervals, with daily workload constraints, regularity and varying flexibility in the requirements, with the goal of minimizing the total travel distance. To tackle this challenge, which deviates significantly from classical routing problems, a genetic algorithm-based solution has been developed and integrated into a user-friendly web application. The algorithm effectively generates feasible and efficient schedules, considering several and diverse factors. Experimental results demonstrate the algorithm’s ability to produce high-quality solutions, outperforming manual planning methods and the other tested approaches. The web application provides an intuitive interface for problem definition and solution visualization, facilitating user interaction and optional refinement.