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Nowadays, transport systems efficiency plays a key role for communities’ liveability and economy, being in addition an important factor in the economic integration of countries. The purpose of the article is to develop multi-stage models of tourist activities for optimizing the development of operating companies. For the implementation of models, the authors evolved the relevant system of organizational-functional support for the development of railway tourism. The research will enable us to take into consideration risks when planning tourist routes by railway, determine the order of construction or start of routes, and assess their profitability. This will provide to earn the expected incomes of all interested parties in tourist activities for the specified period. The authors created economic-mathematical models of the discrete optimal planning of the railway tourism operations. This takes into account conditions of risks and cooperation, and allows to determine which sets of effective routes are the most profitable ones. The results of the realization of the developed models include the task of the succession of the tourist route introduction according to the present and future infrastructure, availability of the rolling stock, etc. In this, consideration is given to obtaining maximum profit from tourism businesses for every participant during an established period.