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A new charter begins as the crew welcomes a billionaire, his fiancée and his five other boyfriends. Massi finds interest in Joy. Gen tries to enact a new agenda. Nathan and Joe's relationship begins to reach a point of no return.

Capt. Lee Rosbach, Kate, Nico, and new crew members set sail on the mega yacht Valor in the waters off the coast of St. Maarten; Kate and Nico have their hands full training inexperienced crew members; Nico deals with a personal tragedy.

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

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.