Pondering the best way to bring my giantess in...My current thought is that after hearing about an upstart pirate that stole another pirates gold and attacked marine ship sounds like the kind of crew she'd like to join and she happens to catch them walking into the tavern ( Which will include the amusing image of her having to carefully squeeze her way through the door. ) And wants to talk business to see if this is really the captain she wants to follow. 

Though that is a rather mundane way to get Hertha in it does seem to be the shortest way to get her involved. But I'm certainly open to suggestions.