This research provides a detailed and systematic update of the traditional sailboat design process, with specific attention being paid to the tools used for evaluation purposes, and in doing so creates an improved and optimized design process for sailboats. More specifically, this report seeks to modify a systems-engineering approach to the ship design process, in order to properly incorporate modern sailboat evaluation techniques as well as elements of traditional sailboat design while providing analysis of a case study from Virginia Polytechnic Institute and State University's ocean vehicle design class. In considering all intricacies of sailboat design and with applications and gradual improvement in quality of design through the use of multi-objective optimization methods, a new sailboat design process evolves, which initially considers a wide variety of design options and alternatives. Specific attention is paid in this process to the evolution of the ordering and analysis of each segment of the subprocesses, reducing design risk through the use of industry standard assessment procedures and ensuring consistent interaction with the customer. In doing so, an improved and effective design process is established, to be used by future sailboat design teams at Virginia Polytechnic Institute and State University. / Master of Science / Boats and marine vehicles of different types have long been a mainstay in the growth and development of this country's military, economic and transportation infrastructure. Whether being used for fishing purposes in the Pacific Northwest or moving oil and gas to different cities along the eastern seaboard, marine transportation plays a critical role in day to day life. Long before the invention of gasoline powered engines, most boats were powered by wind which was harnessed by the use of sails. In the 1800's sailboats were used extensively for fishing, delivering mail and a number of other important activities. Nowadays, the use of sailboats is more geared towards recreational endeavors including racing or simply cruising local waterways. It is the responsibility of the sailboat designer to deliver options and products commensurate with the prospective owner's preferences. As such, it is important for the designer to develop a process or system which incorporates useful tools which can successfully evaluate design alternatives. In doing so, useful information will be produced by which the owner and designer can collaboratively make decisions. Unlike a military or commercial ship, the owner of a sailboat is most likely the main operator and shares a personal connection with the boat. This study modifies a systems-engineering approach to the ship design process, in order to properly incorporate modern sailboat evaluation techniques as well as elements of traditional sailboat design. In doing so, the operation provides a process and tool benchmark for future sailboat design teams at Virginia Polytechnic Institute and State University.