You didn't mention how far you've gone in college; i.e. where are you in terms of graduation? Sadly, I've not seen a "Sailor Wanted" in the classifieds that has anything under the compensation section, outside of the standard "Great conversation, great sailing, great wind", etc. etc. that you can find. Lots of folks dream of hanging out on the boat full time, but usually find that's reserved for the "end" of one's career and rarely at the beginning. Now, if it's being around a dock and boats, and you don't mind some hard work, one could always redirect their studies and focus on something marine diesel mechanics, etc. There are tons of folks in the world earning a small living writing magazine articles, etc. while cruising or circumnavigating, but I'd imagine that particular field is a very competitive and not highly compensated one. You could consider directing your focus towards sales and attempt to become an agent for one of the many brokerage houses that exist. Wouldn't necessarily allow you to hang out on the boat all day, but, you would at least be around the boats when showing them to prospective buyers. I can say this, however, if there was a "job" that consisted of people with experience to teach others to sail or something in that area, then that particular field would more than likely be extremely over-crowded. Speaking for myself, only of course, I'd sure look at a "mid-life-career-change" without blinking an eye. The best path is to "Bill Gates" it: design something that everyone just HAS to have, sell it for billions, then you can do whatever you want to do whenever you want to do it. Oh, or you could just win the PowerBall Lottery and be done with it. Best wishes.