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.

Leigh Anne Tuohy, the inspiration for Sandra Bullock's character in "The Blind Side," and her friends prove to be a challenge for Matt's culinary skills; Jen fails to adhere to the yacht dress code; Matt reconnects with someone from his past.

Nico and Brianna grow closer in spite of 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 with unexpected consequences.

Capt Lee and the crew have their hands full when eight big personalities from Texas come on board. Matt tries to step up his cooking game, Nico tries to show that he is better bosun material than EJ, and Kate tries to protect Jen from lusting guests.

An accident puts Nico in jeopardy; Kate tries to entertain land-locked guests; Brianna grows weary of Jen; Matt is back in hot water with another restaurant owner; Bruno tries to show Kate up with his knowledge of guest relations.

Capt. Lee invites a special guest to come aboard; the crew is surprised by a familiar face; an all-female charter proves to be a handful for Kate and Capt. Lee; as Matt continues to struggle, Capt. Lee takes action to prevent further embarrassment.

Capt. Lee tests Matt as he removes Bruno from the galley and joins the women for dinner; Jen and Kate's working relationship deteriorates; Kyle and Jen grow closer, but Kyle has ulterior motives; Jen reaches her breaking point.

Timothy Sykes comes back and cannot function without his Wi-Fi, which causes pressure for Kate and Captain Lee. Jen is closely followed after upsetting the entire crew. Nico must make a tough choice about his relationship.

Tensions within the crew run high on the final night of the charter season; Timothy Sykes micromanages the crew; Jen tries to be on her best behavior; Nico summons the courage to end things with Brianna; Jen attempts to mend things with Kate.