Hannah continues to struggle with working under the close eye of Captain Sandy. After a mishap with the anchor, Sandy realizes her new deck crew has a lot to learn if they are going to have a successful charter season. Bobby develops a crush on Malia and rushes to her aid when she suffers a freak accident. As the guests enjoy a uniquely themed dinner, a slip of the tongue by Adam threatens to ruin a carefully planned surprise. And, a wild night of partying leads to a major argument as Bobby clashes with Hannah over interfering with his past relationships.