Shipping finance of 2014 has altered substantially regarding that of last decades and the shipping companies’ traditional capital structure of bank lending along with shareholders equity gives way to sophisticated and innovative financing methods forming a new capital structure which is more complicated but serves better the present-day financial needs. Not only constitutes the scope of this dissertation to exhibit the current ship-financing instruments but also to seek the optimal capital structure in terms of cost of capital, economic value added to shareholders and growth prospects that a shipping firm should achieve. The first part of this thesis is dedicated to the display of the most common, available financing methods used on raising funds for either supporting the firm’s operations or financing growth investments and their application in a group of four major dry-bulk shipping companies, Star Bulk Carriers Corp., Diana Shipping Inc., Dryships Inc. and Navios Maritime Holdings Inc. The reason why this shipping segment has been chosen lies on its large volume, market fundamentals and information plethora. Bank lending, bonds’ issuing, equity offering and private equity funds are placed under the microscope for disclosing their benefits and costs may bring about (induce). The second part, being more applied, is concentrated on the abovementioned selected companies analyzing their capital structure and main financial ratios, estimating their Weighted Average Cost of Capital (WACC), seeking for the optimal structure and finally figuring out the outcome of the financing methods implemented. Has their performance been affected by the financial decisions taken and to what extent? Is there a financing method serving as panacea? Which capital structure can minimize a firm’s WACC leading to the maximization of the firm’s own value?