When bad weather keeps Sirocco at port, the crew scrambles to keep a VIP charter broker and her friends happy. Wes announces his choice for lead deckhand, causing tension to erupt. Despite their differences, Hannah and Bugsy attempt to work peacefully alongside each other. Meanwhile, word gets out that Wes and Malia exchanged a kiss during anchor watch leaving their crew mates outraged about crossing professional boundaries. And frustrated by watching the romance grow between Malia and Wes, a heartbroken Adam reveals to Bugs that he and Malia have a secret past. Finally, on the crew's day off in the historical city of Dubrovnik, Adam pulls a prank on Wes that goes a little too far for Wes' liking.

Bugsy's frustration with Hannah reaches critical mass when she calls Hannah out for not pulling her weight. On the final charter of the season, a former guest returns, this time flanked by six beautiful women who test Bobby's willpower when he matches with one on a dating app. Finally, Wes is blindsided when Adam reveals shocking details of a text message exchange between him and Malia, putting Wes and Malia's future in question.