Captain Lee returns to the Caribbean aboard M/Y My Seanna with a brand-new crew and one familiar face, Eddie Lucas, but a critical injury sends Lee to the hospital and puts the fate of the charter season in question. Eddie’s return to yachting is rocky as he deals with a new team and a green but lovable deckhand. Chief Stewardess Francesca sets high standards for her interior crew, but this rubs some the wrong way.
The sudden departure of one of his teammates leaves Shane struggling to adapt to the unforeseen responsibilities on deck. Coming off her clash with Francesca, Izzy begins to question if the interior satisfies her dream of being at sea. While dealing with demanding guests, Rachel lets her emotions get the best of her, and Francesca loses her composure in front of Captain Lee. Meanwhile, James gets caught in the middle of an explosive guest argument.
Ready to let loose in the Caribbean, James instead finds himself disappointed on the first night out. Heads turn as My Seanna welcomes a new crew member, and Izzy makes a surprising decision, much to the chagrin of James. Francesca comes to grips with the ramifications of her emotional outburst. A charter group of thirsty 20-year-olds arrives, and Shane’s mistakes push Eddie’s patience to the edge.
Carrying the weight of the deck team begins to take a toll on Eddie. Feeling out of his element, James struggles to connect with his crewmates. Mistakes from a few people fracture the charter, and Captain Lee is forced to level with the crew after a series of dangerous mishaps. Ultimately, Shane’s repeated follies push Eddie over the edge.
Shane tries to redeem himself after getting caught sleeping on the job. Meanwhile, Ashling excels in her duties on deck as Elizabeth suffers the scrutiny of Francesca. In the galley, Rachel is excited to finally have refined guests on board, but things are not always as they seem.
After a caviar mishap, the primary’s 50th birthday dinner teeters on the edge of disaster, and Rachel finds herself embroiled in interior drama. As Shane’s career hangs on by a thread, Francesca’s frustrations with Elizabeth build.
Following Captain Lee and Shane’s conversation, the deck team must deal with the fallout. Rachel struggles with her long-distance relationship while James and Elizabeth’s attraction to each other becomes obvious. Tensions reach a new high after a critical mistake pushes Francesca to consider a stew replacement, and Rachel makes an impulsive decision, taking the whole crew by surprise.
A new face joins My Seanna as the repercussions of Rachel’s decision cause uncertainty for the charter. Elizabeth gets encouragement from her crew members, and Captain Lee steps in after Eddie is put into a precarious situation.
As the fallout from her impulsive decision lingers, Rachel attempts to regain Captain Lee’s trust, but her antics annoy Eddie. Meanwhile, a demotion within the interior department sparks controversy, and Francesca feels lonely. Bonds on board grow stronger than ever as a romance heats up between Elizabeth and James while Izzy opens up about her painful past.
Elizabeth struggles to keep her budding relationship under wraps; James finds himself at the center of the rumor mill; Izzy feels sick; when a drunk charter guest crosses the line and defies Capt. Lee, the captain is forced to lay down the law.
Izzy must play musical bunks, leaving Francesca and Eddie to address professionalism on deck with Elizabeth and James. Meanwhile, Izzy’s condition worsens, and she’s put into quarantine. After a challenging charter, Captain Lee grants the crew a relaxing day off at a resort, only for them to be mortified by Rachel’s erratic actions.
Rachel's antics continue to torment the crew, and Elizabeth finds herself in the doghouse. Sharing his soft and vulnerable side, Captain Lee opens up to Francesca about a personal tragedy. As Izzy's health continues to be a struggle, Eddie sends her off for medical care, but more crew members fall ill, and Francesca worries if they'll make it through the next charter.
James plays games at Elizabeth's expense, and Eddie presents Izzy with an interesting opportunity. The team rallies together for a beach cleanup, but warm and fuzzy feelings quickly diminish when Francesca finds out that subordinates slept in a guest cabin without permission.
Pushed to the brink, Francesca loses all trust in Elizabeth while Captain Lee shares an unfortunate bond with the charter guests. Rachel continues to grow frustrated with the interior over miscommunication, and Elizabeth’s high expectations for her 30th birthday fall short. Ashling decides to lie to the primary’s son, and the crew grows fearful of COVID-19 as it ramps up back home.
Ashling suffers the consequences of her white lie while Izzy’s promotion creates waves on deck and Rob makes his feelings abundantly clear. A condiment mishap fuels the contention between Francesca and Rachel as Elizabeth spends the charter focusing on James instead of her job.
Francesca finally comes to a decision regarding Elizabeth's future on deck. Rachel's feelings toward the interior take a toll on the crew. As Izzy and Rob's relationship takes a dark turn, James reveals a shocking betrayal.
The yachties open up about all the crew shake-ups and drama that happened in the season; an unexpected accusation shocks some of the crew.