Over the past two summers I have taught Sailing at Nepean Sailing Club. First in White Sail, then in Bronze. The following is an account of why I don’t think teaching sailing is a good summer job (unless of course you are going into education and are really just looking for something to put ion your resume). The biggest issue with teaching sailing really two-fold. First there is a very high initial investment of time and money required to get to the point where you can even teach sailing.