Introduction: As the diving population is ageing, so are the diving instructors. Health issues and the use of prescribed medications are more common when ageing. The death of two diving instructors during one weekend in 2017 in the Netherlands, most likely due to cardiovascular disease, motivated investigation of the prevalence of relevant comorbidities in Dutch diving instructors. Methods: All Dutch Underwater Federation diving instructors were invited to complete an online questionnaire. Questions addressed diving experience and current and past medical history including the use of medications. Results: A response rate of 27% yielded 497 questionnaires (87% male, average age 57.3 years [SD 8.5]). Older instructors were over-represented among responders (82% of males and 75% of females > 50 years versus 66% of males and 51% of females among the invited cohort). Forty-six percent of respondents reported no current medical condition. Hypertension was the most commonly reported condition followed by hay fever and problems equalising ears and sinuses. Thirty-two percent reported no past medical condition. Problems of equalising ears and sinuses was the most common past medical condition, followed by hypertension, joint problems or surgery, and hay fever. Fifty-nine percent used non-prescription medication; predominantly analgesics and nose or ear drops. Forty-nine percent used prescription medicine, mostly cardiovascular and respiratory drugs. Body mass index (BMI) was > 25 kg·m-2 in 66% of males and 38% of females. All instructors with any type of cardiovascular disease were overweight. Conclusions: Nineteen percent of responding diving instructors suffered from cardiovascular disease with above-normal BMI and almost 60% used prescribed or non-prescribed medication. Some dived while suffering from medical issues or taking medications, which could lead to medical problems during emergency situations with their students.