As the season begins, an unfamiliar face welcomes the My Seanna crew aboard that shocks everyone. Chief stewardess Heather's frustrations build when she is confronted with a difficult task. First officer Eddie struggles to bring his team up to speed while also dealing with changes in the wheelhouse. Lingering tension from last year's charter season threatens the harmony of the yacht.

Captain Sean’s hands-on managerial style continues to frustrate Eddie as the staff works hard to pull off an elaborate beach picnic for the guests. Fraser feels pulled in multiple directions by his chief stew Heather, which leads to housekeeping falling through the cracks much to the displeasure of the primary. On the first night out two crew members hook up, which could lead to stormy waters ahead for the whole team. Captain Lee arrives but will his new crew be able to get their act together before the next charter?

Captain Lee lays down the law as the crew gets ready to welcome their second charter group onboard My Seanna. Eddie is determined to promote Jake to lead deckhand but Captain Lee has reservations. Heather is on a mission to redeem herself from the first charter's housekeeping mistakes and improve her interior team's performance issues, much to her stews' chagrin. Rachel confronts Eddie about the unsavory remarks he said about her behind her back last charter season and Rayna finds a new friend in Fraser. A rowdy bunch arrives onboard and their drunken antics prove to be much more than the crew bargained for.

The crew of My Seanna experiences less than desirable behavior from one of the charter guests. Jake struggles with his new position and Jessica starts begins to remember how much wear and tear a charter season can take on your body. Wes and Jessica build on their friendship while the deck team's silly mistake leaves Eddie and Captain Lee furious.

Eddie deals with his relationship fallout as Jake and Rayna try to figure out their feelings after Jake’s revelation. After losing his walkie, Fraser starts to feel like he’s failing in his job while Jessica gets upsetting news from back home. The deckhands make yet another mistake that pushes Captain Lee and Eddie to their breaking points.

Heather and the crew plan an 80s themed surprise party for the primary’s 75th birthday but things go south when everything doesn’t go as planned. Frustrated by the deck team's mistakes, Eddie is forced to put his first officer training on the backburner to babysit his crew. Jessica's unhappiness on the boat grows as Fraser and Heather's bond develops. The crew takes an interest in setting up Wes & Jessica romantically but Jake makes a bold move of his own on another crew member, leaving everyone shocked.

As small mistakes from the deck team continue to mount, Heather feels like she is at a dead end with Jessica and decides to make a change. A breast cancer survivor arrives and has very particular tastes to the amusement of Chef Rachel. Rayna and Fraser’s frustrations continue to grow as Captain Lee and Eddie’s working relationship is tested.

Jessica is unmotivated by service but welcomes a budding romance with Wes as a happy distraction while Captain Lee and Eddie grow weary by the deck crew's performance; a meat and family vacation takes an awkward turn.

Captain Lee is frustrated with Eddie and the deck team for their repeated mistakes. Rayna feels like her performance on deck is being affected by other crew members as she reflects on the night out. A guest whose jaw is wired shut creates chaos for Rachel while Jessica reveals shocking news to Heather.

Rachel continues to struggle with the primary's requests while Heather and Fraser have their hands full as they work without a third stew; past actions throw Heather into a spiral, while Rayna battles with how to feel about her crew's transgressions.

The promise of a new stew brings out Fraser's insecurities much to Heather's dismay; a group of military guests arrive with demanding dietary restrictions which leads to a challenging dinner service for Rachel.

Love is on full display as U.S. Navy vet couples renew their vows onboard My Seanna; Eddie gets to the bottom of Rayna's frustrations and is surprised by what he uncovers; Fraser's insecurities are tested as a new face arrives in St. Kitts.

Eddie struggles with how to earn back Rayna's trust while the interior team deals with a demanding group of Hamilton-obsessed guests; Capt. Lee is worried that the crew's five-star service could be slipping as Rachel attempts an extravagant dinner.

An exhausted Rachel takes out her frustrations on Heather as she struggles to focus during the last dinner service; long-simmering tensions amongst the crew come to light during the crew's final night out.