Honestly, I feel pretty safe in saying that this isn't one of the most well-designed quests. It's a basic bombing quest, except they seem to have forgotten all the lessons they might have learned from previous bombing quests in Ogri'la and Quel'danas.
First, Instead of a personal flying mount, you have to bomb the ships from a zeppelin that makes its rounds every few minutes, so you have to wait for it dock before beginning the quest. Secondly, the pirates and ships you have to bomb are scattered very far apart, often hidden by icebergs until the last moment, and don't seem to respawn very fast. All of this adds up to making the quest somewhat of an exercise in frustration solo.
However, there is hope.