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Bronwyn finds happiness in her new relationship with Brandon; Whitney realizes she needs to make big changes in more than one aspect of her life; after Robert Jr.'s Homegoing, Lisa brings the girls together for a ski day to lift their spirits.

Daisy hosts a Seder for the group that ends up being a less-than-festive affair; Hailey divulges the trauma of her past; Erika takes a step towards growing her family; Erin and Jessel duke it out over coffee.

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.