Captain Lee, Kate and Nico are joined by six new crew members as they embark on a new charter. Kate and Nico have their hands full as they are charged with training a few inexperienced crew members. Nico is also dealing with a personal tragedy.
The crew welcomes their first charter guests. Mistakes continue to follow the crew and Captain Lee finds himself having to get more involved. During the first night out, the alcohol flow reveals some of the crew's true colors and romantic intentions.
Chris Brown's decision to nap finds him in the crosshairs with Captain Lee. Kate meets a cute sailor and has a rendezvous on his boat during charter. Matt faces his first challenge of the season with sushi dinner and a tequila pairing.
Jesus and Kate get to know each other. Chris Brown makes a pass at Brianna. A group of guests arrive ready to party. Matt makes a move on Brianna while Nico's wandering eye might get him in trouble. Nico and the exterior make a disastrous mistake.
Captain Lee makes a decision regarding the crew's re-configuration which rocks the team to its core. Kate plans an anniversary surprise for the charter guests that fizzles. Meanwhile criticism from the charter guests sends Matt spiraling into shame.
Nico is pushed to his breaking point under the leadership of boson EJ. Matt continues to unravel after his date with Brianna. Captain Lee makes a staffing decision. Jen feels under-appreciated in her department which causes strife with Brianna.
Leigh Anne Tuohy and her friends prove to be a challenge for Matt's culinary skills. Nico settles into life as the number two on deck but questions if he can stick out. Jen tries to impress Kate but fails to adhere to the dress code.
Nico and Brianna grow closer despite Nico's girlfriend back in Chicago. Unexpected news sends Matt into an alcohol fueled day off. Kate challenges Jen and Brianna to a stewardess speed test which has unexpected consequences.
The crew have their hands full when eight big personalities come on board. Matt attempts to step up his cooking game. Nico attempts to show Captain Lee he is better bosun material than EJ, but a beach picnic might prove too much for him to handle.
An accident puts Nico in jeopardy of finishing out the rest of the charter season. Kate is forced to leave her stews behind on the yacht as she attempts to entertain the not-so-pleased-to-be-landlocked guests. Matt is back in hot water with another restaurant owner.
Captain Lee has a special guest come aboard and the crew gets to see a different side to their leader. A familiar face from the past surprises the crew and immediately has eyes for Jen. An all-female charter proves to be a handful.
Captain Lee tests Matt as he removes Bruno from the galley, and joins the women for dinner. Kyle has ulterior motives as he and Jen grow closer. Nico is conflicted as his feelings for his ex and Brianna grow. Jen reaches her breaking point.
Timothy Sykes is back and can't live without his WiFi. Kate and Captain Lee know the expectations that are required for a guest of this magnitude and are feeling the pressure. Jen is under intense scrutiny after she has upset the entire crew.
It's the final night of the charter season and tensions within the crew are running high. Jen attempts to be on her best behavior. Nico gathers the courage to end things with Brianna, while Jen makes a final attempt to mend things with Kate.