Introduction-Most of the literature on sailing injuries is centered on competitive sailing, often involving a single regatta. The aims of this study were to provide a description of the types of injuries and illnesses sustained during amateur offshore cruising events, estimate their incidence, and investigate potential risk factors for injuries.Methods-We conducted a cross-sectional survey of self-reported sailing-related injuries and health issues during 4 different events organized by the World Cruising Club between 2014 and 2015. Prior to departure, sailors received an injury or health issue report form to complete during their sailing event. Questionnaires were then collected at the end of each event. Bivariable (Student's t tests and χ 2 tests) and mutilvariable logistic regression were used to study the associations among injuries, health issues, and the characteristics of sailors or sailboats.Results-The incidence of injuries and health issues among the respondents was 1.08 and 1.01 per 10,000 nautical miles, respectively. Smaller boats (P<0.001) and crews with less experience with the current boat (P<0.001) were associated with reporting of more injuries. Most of the injuries were reported during favorable weather conditions. Health issues were more frequent on smaller boats and with women (P=0.008), who reported significantly more seasickness (P<0.001), anxiety (P=0.037), and skin rash/fungal infection (P=0.021).Conclusions-Injuries and health issues are relatively common among amateur offshore recreational sailors, but severe injuries are rare. Smaller boats and having less experience in sailing with the current boat were associated with more injuries. Preventive strategies should include a sailing experience requirement on the boat being sailed for all crew members, increasing the minimum boat size requirement for sailing events, and mandatory first-aid training prior to a cruising event for all crew members.