I've only built one boat, so this is something I haven't tested over and over again...
I had four soldiers, a frigate, and my sovereign in a city. I tried to move them all out into the ocean. Only the soldiers and frigate moved out. I couldn't get the sovereign to board the boat. I tried unloading the soldiers first, and then getting the sovereign to enter. I tried going back into the city, going onto a beach tile...couldn't get the sovereign on board at all.