The paper presents a simulation tool for automated interactions between insurance companies and their clients during the travel insurance buying process. Insurance deal evaluation model using price and insured risks has been developed based on the study of the Latvian insurance market. The proposed model is used together with well-known agent auction protocols, thus providing a multi-agent negotiation protocol. It allows automating one-to-many negotiations between client and insurance companies simulating electronic insurance policy marketplace. The simulation tool has been developed using the MASITS methodology and tool, thus providing a case study for the methodology and tool for a new type of systems.