So, I've noticed that the Pirates event caters to the high-powered, much like a lot in this game. You might think, "oh, well, it's motivation to become more powerful". True, but then the people above you will also be becoming more powerful, so many of us in the lower slots don't have a shot at all unless they stop playing.
The Pirates event is a glaring example of that, especially since it is server-wide, and not just realm-wide, which means that anyone who is not top tier pretty much has no chance of completing a sail. You'd think, since a "successful" sail is a requirement in the assistant's list, and not just a sail, that it would be a bit more fair. So, I suggest one of 2 options to give everyone more of a chance to complete it. Option 1) Make it realm-based and not server-based. Less people watching means more chances.
Option 2) The only way a boat can be attacked once it has sailed is if the attacker is also on a boat. Once people board a boat, add a 30 second to 1 min. timer, the "preparing to sail", and at that time, people not on boats can attack. Once you sail, another boat can sink you. It makes sense, for how can someone not on a boat attack someone on a boat in the middle of the water?