Pairwise route synchronization constraints are commonly encountered in the field of service technician routing and scheduling and in the area of mobile care. Pairwise route synchronization refers to constraints that require that two technicians or home care workers visit the same location at exactly the same time. We consider constraints of this type in the context of the well-known vehicle routing problem with time windows and a generic service technician routing and scheduling problem. Different approaches for dealing with the problem of pairwise route synchronization are compared and several ways of integrating a synchronization component into a metaheuristic algorithm tailored to the original problems are analyzed. When applied to benchmark instances from the literature, our algorithm matches almost all available optimal values and it produces several new best results for the remaining instances.