Capt. Sandy embarks on a new charter season on the beautiful waters of the Italian Riviera; two of her stews have unprecedented issues getting to the yacht; the deck team faces unforeseen obstacles; Capt. Sandy has to make a difficult decision.

A deckhand steps up after a surprise incident; the crew is challenged by seasick guests, which leads to an impromptu excursion to Portofino; Natalya attempts to keep the interior team afloat before she meets her new chief stew for the first time.

Tumi and Natalya grapple with differences in management styles; Kyle and a new deckhand join the crew on board; the interior team scrambled to keep everyone happy; Tumi and Chef Jack have trouble with communication.

A stew is torn between their open relationship and a growing onboard flirtation. The deck team’s communication is strained during a rough docking. The rivalry amongst stews spills into the workplace and Capt. Sandy is forced to intervene.

A deckhand’s questionable work ethic gets on the rest of the team’s nerves; two stews hope to bury the hatchet for the sake of crew morale; past charter guests arrive with a new baby and a lot of energy; things get heated between two deckhands.

The whole crew is involved in an elaborate pirate-themed day for the charter guests. The bosun’s cool-under-pressure vibe is challenged during a very tight docking. The chief stew and chef hit their stride as a team while a stew starts to redefine their friendships within the department. The bosun and a stew finally kiss, challenging the stew’s feelings about their open relationship.

Some of the crew takes notice of a group of attractive young women chartering the yacht; a miscommunication between the chief stewardess and the interior department leaves them uncertain; Capt. Sandy has an accident.

The bosun causes confusion when he shifts his romantic focus as the chef gives in to temptation. The charter guests continue the festivities with the crew after the charter ends. An argument between the crew could be the one that ends friendships.

The crew's day off at a beach resort is fraught with tension and division, lingering from the previous night's kerfuffle; the bosun's new romance ignites; a crew member confesses their frustrations and puts Captain Sandy in a difficult position.

A new crew member may lack some necessary skills; Capt. Sandy gives it her all trying to persuade a deckhand to stay on the boat; in scenic Portofino, the deckhands face their most challenging docking yet; a stew thinks the chef is out to get them.

The chef and a crew member clash; romance blossoms, bringing two yachties closer together; the chief stew's frustration grows as her new team member struggles with the workload; Capt. Sandy loses her patience with the bosun.

Capt. Sandy has a difficult conversation with the primary charter guest after someone in their group becomes unruly; the bosun's interior love interest develops feelings for him; the chief stew's problems with a crew member reach a boiling point.

A returning guest seeks redemption on a charter, but the crew struggles with two members down. With their job hanging in the balance, a stew tries to find their footing to save their position. A crew member’s complaint about the crew food lands the chef in hot water with Capt. Sandy.

The bosun's texting with a familiar chief stew turns into a damage control crisis; the chef faces a culinary challenge with a blindfolded dinner; Illness strikes the lead deckhand.

Due to inclement weather coming in, the final charter of the season risks remaining docked; the chief stew and bosun work tirelessly to organize activities for the guests, relying heavily on the assistance of the fourth stew.

The chief stew entrusts two crew members with the task of organizing a foam party for the guests; the party falls short of expectations; the bosun lands himself in hot water when he's caught texting again; the crew's final night out takes a turn.