There is uncertainty as to whether the stability criteria in the Dutch regulatory framework for commercial cruising vessels are safe and obtainable for the current Dutch commercial sailing fleet. Therefore, this paper aims to determine a suitable set of intact stability requirements for monohull sailing vessels operating under the Dutch flag, striking a balance between safety and practicality. A literature review was conducted to identify potential stability risks and the state-of-the-art of sailing stability criteria. Models of representative vessels in the Dutch sailing fleet have been defined to study the practicality and safety level of various stability criteria in more detail. It is concluded that the current criteria are not obtainable for sailing yachts designed to sail at large heel angles. Moreover, it was found that the current criteria cannot identify vessels that can be vulnerable to squalls or waves. Therefore, a new set of criteria is proposed, which is more practical for vessels in the Dutch commercial sailing fleet, whilst providing an improved measure of safety.