Stassi plans an epic surprise party to celebrate Jax and Brittany’s engagement, but Sandoval and Ariana question Jax’s ability to commit to one woman for the rest of his life. James attempts to work his way back into the group’s good graces, unaware that Kristen has hatched a plan that might ruin his romance and banish him for good. Stassi seeks Lisa’s approval for her new beau Beau, and Lisa must decide whether Jax deserves another chance to work at SUR.
Captain Lee has a special guest come aboard and the crew gets to see a different side to their fearless leader. Meanwhile, a familiar face from the past surprises the Valor crew and immediately has eyes for Jen. An all-female charter, who love Jesus and cocktails, proves to be a handful for Kate and Captain Lee. As Matt continues to struggle in the galley, Captain Lee takes action to prevent further embarrassment.
Captain Lee tests Matt as he removes his "sous-chef" Bruno from the galley, and joins the women for dinner. Jen feels defeated as her and Kate's working relationship deteriorates. Kyle and Jen grow closer as she finally has a friend she can lean on, but Kyle has ulterior motives. Nico is conflicted as his feelings for his ex-girlfriend and Brianna continue to grow. Jen reaches her breaking point and things turn physical after a dinner gone sour.
Previous guest and finance wizard Timothy Sykes is back and once again can't live without his WiFi. Kate and Captain Lee know the high expectations that are required for a guest of this magnitude and they are feeling the pressure on this last charter of the season. Jen is under intense scrutiny after she has upset the entire crew, and most importantly her boss Kate who puts her through the ringer on this last charter. Meanwhile, Nico struggles to make a decision about his relationship. Kate helps Matt plan the dinners to finish the charter season on a high note.
It's the final night of the charter season and tensions within the crew of motor yacht Valor are running high. All departments are working overtime as return charter guest Timothy Sykes micromanages the crew to execute the perfect surprise for his guests on board. In the wake of her explosive fight with the crew, 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.
Captain Lee and chief stew Kate welcome seven new crewmembers aboard luxury M/Y Seanna, as they travel outside the Caribbean for the first time ever to explore the tropical waters of Tahiti. Kate has high hopes for her experienced interior crew, however, bosun Chandler finds his hands full training a fisherwoman-turned-third deckhand. Neither department is prepared for the return of legendary charter guest, Foam Party Steve.
As Captain Lee and the crew of My Seanna continue to cater to Steve’s unpredictable antics, Chandler struggles to find his footing with Captain Lee and his deck team. Meanwhile, the interior unveils some of their cracks during a busy dinner service. Later, as the crew celebrates their first night in Tahiti, Ashton proves to be a ladies man and Chandler is pushed to his limit after an explosive encounter with Rhylee.
Rhylee's outburst with Chandler puts her at odds with the entire Deck Team. Meanwhile, Kate and Josiah comfort an emotionally broken Caroline after she receives getting some devastating news from back home. Captain Lee and the entire crew of My Seanna have their work cut out for them when a returning disgruntled charter guest arrives.
Captain Lee worries that Chandler is mismanaging his deck team after hearing some unsettling news. Ross confronts Rhylee after she oversteps her boundaries. Meanwhile, Caroline feels left out vents her frustrations to Kate. The crew of My Seanna suspect a blossoming romance and later Caroline overhears a conversation that sends her into an emotional whirlwind.
Rhylee struggles to keep her attitude in check as she and Chandler continue to be at odds. The crew welcome aboard a group of Silicon Valley investors who are social media obsessed. Later, Caroline wakes up with a mysterious foot injury and has difficulty pulling her weight on charter while Kate struggles to cater to the charter guest's odd and often naked behavior.
As Chandler’s decision making frustrates the deck crew, Rhylee and Ashton grow desperate for a change of bosun. The charter guests overcome their fears by swimming with some scary ocean predators. Later, as Ashton makes on move on Rhylee after a wild night, Kate tells Caroline her foot needs to heal or she’ll have to go home. When the mistakes keep piling up for Chandler, Captain Lee decides to confront him in a sit down.
The crew welcomes aboard their largest group of charter guests yet, including two young children, posing new challenges for everyone. While Chef Adrian jumps through hoops to please all their preferences, Chandler tries to redeem himself with Captain Lee. After being banished to the guest cabins with her injuries, Caroline struggles to find her place back with the interior, but her sour mood pushes Adrian to snap.
Chandler is left at odds with Captain Lee and the entire Deck Team when an oversight leaves the charter guests stranded at an off-boat excursion without basic amenities. While Kate and Adrian pull out all the stops to deliver on a traditional beachfront pig roast Luau, its success is threatened when a guest is injured due to Chandler’s oversight. Caroline struggles to keep up with the demands of the charter, leaving her frazzled, frantic and prone to more errors. Following the calamitous charter, Captain Lee calls Kate and Chandler to the wheelhouse, ready to implement necessary changes to the team.
Captain Lee comes to a decision about restructuring the deck team. Meanwhile, Caroline is pushed to make her own decision regarding her place on My Seanna. During a fun crew night out, Ashton proves to be a ladies’ man with the locals, while Rhylee ruffles some feathers with Adrian. Captain Lee confronts Kate about a sensitive situation and a reconfigured crew welcomes their highest profile charter guests yet.
My Seanna struggles to pull off a successful charter on the heels of two dramatic exits from crew members, Chandler and Caroline. Tensions rise as newly-appointed bosun, Ross, finds himself at odds with an easily-riled Rhylee. When replacements Tyler and Laura join the crew, the ship is turned upside down. While Kate and Josiah adjust to their new stew’s critical disposition, Adrian and Ashton both compete for her undivided attention. As their sixth charter begins, a shocking accident threatens the life of one of the deckhands.
When a tropical storm forces the crew to move the party from the boat to dry land, a tell-all game threatens to reveal crew secrets that may be too explosive to share. Max finally gets real with Quenton about his feelings on his place in their family and his possible future with Vanessa, and Korey learns of a work emergency back home that might cut his trip short. Meanwhile, Danielle reveals that her hostility towards Rachel stems from a secret affair early in her relationship with Barrett.