Veterans Captain Lee, Kate, Ben, and Kelley are joined by five new crewmembers as they prepare the luxury yacht Valor for a new charter season. The crew welcomes their first charter guests, a social media obsessed darling along with her friends. Kate is tasked with breaking in two new junior stewardesses, but when one misses her flight Kate is unsure if she will be able to handle the charter shorthanded. With added pressure of being a first time bosun under Captain Lee Kelley has his hands full with his headstrong senior deckhand Trevor. Ben and Kate must find their new middle ground as Ben comes to grips with Kate's new relationship.

Kelley makes a decision on how to proceed with Trevor. The new charter guests prove to be a handful with a very pampered poodle. Ben and Kate clash again, while Kelley continues to deal with Trevor's poor attitude. Meanwhile, Kelley gets a call from a loved one and Trevor proves old habits die hard during the crew's second night out.