I love trivia. Probably my age, or my geek background.
When I go over right-of-way rules with students, I tell them this is a trick question. Sailboat and kayak - who has right of way? Any answer they give is wrong, although it's interesting to see the reasoning behind it (kayak more maneuverable, etc.), and that in itself is useful - on the water, what would you do?. The answer is that it's not covered in the Naviagation Rules. Really. I was a kayaking instructor for 10 years, and in a moment of boredom, I read the entire Navigation Rules looking for things that applied to kayaks. Exactly one reference:
Rule 25 - Sailing Vessels Underway and Vessels Under Oars
(ii) A vessel under oars may exhibit the lights prescribed in this rule for sailing vessels, but if she does not, she shall exhibit an all around white light or have ready at hand an electric torch or lighted lantern showing a white light which shall be exhibited in sufficient time to prevent collision.
Not useful for right-of-way. O course the generic any vessel rules apply to a kayak (sailboat overtaking a kayak, or for that matter a slow moving powerboat, must give way).
In an advanced dinghy class when the subject was sailling backwards, I was told that when you sail backwards, you have no rights. It seemed odd to me, as in my boredome-induced reading of the rules I didn't remember encountering that (and I had been an avid sailor before kayaking). So just now, I went through the Rules, and the only rule I could find to cover the situation was the generic one:
Rule 12 - Sailing Vessels
(a) When two sailing vessels are approaching one another, so as to involve risk of collision, one of them shall keep out of the way of the other as follows:
(i) when each has the wind on a different side, the vessel which has the wind on the port side shall keep out of the way of the other;
(ii) when both have the wind on the same side, the vessel which is to windward shall keep out of the way of the vessel which is to leeward;
(iii) if a vessel with the wind on the port side sees a vessel to windward and cannot determine with certainty whether the other vessel has the wind on the port or on the starboard side, she shall keep out of the way of the other.
Here's the image:
Not very practical, I admit, but I hope it will please trivia fans. Although I did manage to get a Bahia on a backwards beam reach very near some Cal Adventures students, who seemed impressed but seemed to have no idea what to do (probably the same if I had been sailing forwards).
The racing rules are different (as they are for a lot of things). Here backwards sailing is covered in Rule 22.3 (which is marked as "changed" in the 2013-2016 edition of the Rules):
22.3 A boat moving astern through the water by backing a sail shall keep clear of one that is not.
I was amused to discover that windward and leeward don't always mean the same thing in racing as in the Navigation Rules. Here's an example:
Under the Navigation Rules, Orange is Leeward and has right-of-way. Under the racing rules, Green is Leeward and has right-ot-way (refer to the definition of Windward/Leeward in the racing rules to find out why, if you care).
So here's another trivia question that AFAIK has no commonly accepted answer. I've heard instructors teach to heave-to on starboard tack, if possible, as you have right-of-way. The question is when you are hove-to, are you under way or are you a vessel not under command:
Rule 3 - General Definitions
(f) The term "vessel not under command" means a vessel which through some exceptional circumstance is unable to maneuver as required by these Rules and is therefore unable to keep out of the way of another vessel.
(i) The word "underway" means that a vessel is not at anchor, or made fast to the shore, or aground.
You can find a huge debate on the web on this question with no clear answer (and, apparently, no case law). In practical terms for the South Basin, our 15' boats are not requjired to display NUC shapes, and presumably someone is keeping watch, so some of the debate isn't applicable. My personal opinion is that if you're hove-to reefing or shaking out a reef, you're a vessel Not Under Command (as you can't easily maneuver to avoid a collision), and any other skipper would be stupid to claim rights over you. Just my opinion.