Due to the exceptional complexity of the propulsion system (sails), square-riggers form a special group of sailing vessels. In modern pleasure and sport sailing, simple Bermuda (triangular) sailing rigging prevails, which is widely discussed in the literature, both in terms of theory and numerous experiments. The literature on the theory on square-riggers is, in turn, limited mainly to the description of good sailing practice developed over the centuries. Its important element was maximising vessel speed, but this discussion has not been documented by scientific research. This paper presents the significant parameters influencing the speed of a square-rigged sailing vessel and selects those which are the most important from the point of view of its maximisation. The paper also proposes methods and measurement systems which optimise selected parameters affecting the achievement of higher speeds. The paper describes the types of speeds of typical sailing vessels, provides a historical synthesis of sailing ships with respect to their speed, and presents a selection and description of the parameters affecting the speed of modern square-rigged vessels. The paper ends with a proposed method and measurement system for experimental research aiming at rigging optimisation in a square-rigged sailing vessel from the point of view of maximising its speed.