Just make very, VERY sure it is a SAILBOAT captain you are hiring. I know a hundred 'captains' around here I would not let pilot a jonboat, across the board idiots that are mind boggling stupid. I don't know what this license entails, and don't care, I with regularity move boats so far upwards of 82 tons. Don't even WANT a ticket from some agency that says I 'know how'. Really, how many courses have you ever been to that was filled to capacity with mouth-breathers than can barely read. A couple of years ago I took a basic navigating course over at the college here because it was winter, I was bored, and knew the instructor as being a long time sailor, not boater. Three of them were late for the first course because they couldn't find the college, and one of them was late twice with the same excuse. An untrainable I.Q. is 60 or below. One guy had maybe an 80, and I'm being gracious. (Forest Gump is estimated as 75). They all passed. Of COURSE they did, they paid money.
While this is not the criteria you are searching for, find a SKIPPER that knows sailboats. I don't even know of but two around here, Wayne and Jiles professionally, and I know a lot of people on the water. Few of which would ever pilot a boat for me. Dang man, I hate to say it, but it truly sounds like a problem. You KNOW things are bad when folks call ME to do it..
Oh yeah, I think around here it runs about 3 bills a day for a 'captain'. Two if someone is doing it for the fun of it and doesn't need any money.