[canucksailorguy]

Jordan, that's interesting you experienced those things. That's the first time I've heard of this. From the mariner's side of things, it's very rare. I've had one 'hint' which was easily ignored and not pushed, and one outright request, which I've mentioned - that was in Hemingway. My experience parallels that of other boaters.
As for the passport thing, I suspect it's because you, as a Canadian tourist, are clearly not going to or through the US and the stamp isn't an issue. Again, for mariners, the issue is that the boat may be going on to the States, where the stamp would create a problem. It's interesting to see these differences in procedure, since I've not gone to Cuba other than by boat.
Did they give you a tarjeta, a small card, when you arrived?