This paper analyzes the operations and financial statements of two economic entities, based in the Republic of Croatia, which are engaged in the activity of transporting dry bulk cargo by sea, and their market value was estimated using several methods. The paper presents the theoretical and applied aspects of the assessment and indicates the recommendations that may arise from the results. In the theoretical part of the paper, the fundamental determinants of financial analysis and valuation are presented, including the regulatory framework and approaches for selecting valuation methods. In the practical part of the paper, it was shown that the results of the application of a certain model depend on the indicators of the activity, but also on the characteristics of the company that is the subject of the assessment. As there is no legally prescribed valuation method, the choice of method is related to the interests of the seller, acquirer or neutrally to the needs of state institutions (continuation or termination of business). The business of shipping companies for the transportation of cargo by sea is interesting for assessment and analysis, considering that they operate in a market that is global and extremely volatile under the influence of various macroeconomic, political decisions and shipping regulations, as well as freight price movements. Companies that operate on that market have significant differences in the results of operations in short periods of time, which presents a challenge to the management of these companies to overcome crises in business. The aforementioned is also reflected in the movement of the prices of shares of shipping companies on the stock exchanges. From the obtained evaluation results of the selected companies, a significant deviation from the value of their shares and differences in the estimated values using different methods can be observed. The above represents the negotiation framework for possible business combinations and space for the formation of a unique recommended value.