Captain Lee and his returning crew, Kate and Nico are joined by six new crew members as they embark on a new charter season in St. Martin aboard the luxury yacht Valor. Kate and Nico have their hands full as they are charged with training a few new and inexperienced crew members before the first charter of the season. Meanwhile, Nico is dealing with a personal tragedy which is affecting him more than he's let on.

Tension is high as Kate and Nico continue to struggle operating with a crew of newbies; the crew welcomes their first charter guests; Captain Lee finds himself having to get more involved in troubleshooting the problems the crew faces.

Chris Brown's decision to take a nap lands him in hot water; the new guests prove to be a handful; Kate meets a cute sailor and visits him on his boat; Matt faces his first challenge of the season with sushi dinner and a tequila pairing.

During their night off, Jesus and Kate get to know each other; Chris Brown makes a pass at Brianna; Nico marks the 3-month anniversary of the passing of his brother; a group of fun charter guests arrive ready to party.

Capt. Lee makes a decision regarding the crew's re-configuration; Matt and Brianna mistakenly go to a nude beach; Jen grows weary with unfair treatment; Kate plans an anniversary surprise that fizzles; criticism 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, which causes problems for Kate; Capt. Lee makes a staffing decision.