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.

Captain Sandy embarks on another season in the Mediterranean out of the world famous yachting hub, the French Riviera. Hannah returns as chief stew determined to put her head down, focus on her work and her relationship with Captain Sandy. After enduring heartbreak, Joao returns with a promotion as Bosun hoping to prove to Captain Sandy he can lead a deck team that includes his best friend and partner-in-crime, Colin. Cordon Bleu trained chef Mila takes control of the galley, but immediately falls ill on day one, forcing the crew to rally and help get the boat in shape in time for the first charter. When the first guests arrive and chef Mila, who is a department of one, is still battling illness, Sandy and the crew wonder if she’ll be able to perform her most basic duties.

Colin faces a tough decision and Anastasia accepts her new role, but Sandy wonders whether if she’s now phoning her job in. An all-female group come on board and do their best to flirt with the deck crew. Jack and Aesha move in together making Travis feel isolated. And a familiar face returns that has Hannah on her toes.

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.

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.

With both Hannah and Jamie down, Captain Sandy steps in to support her crew. Adam feels like his chance at redemption is foiled when charter guest Kenny requests an impromptu beach picnic. As Brooke and Kasey step up to fill the void for being down a stew, they notice that it’s smoother sailing. Meanwhile, Conrad is torn between being a shoulder to lean on for Hannah and assuring Sandy that he’s fulfilling his job on deck. And Hannah crosses a line with Sandy that could end her charter season a lot sooner than she thought.

Captain Sandy’s patience is tested when Hannah disobeys a direct order. Meanwhile, Adam concentrates on delivering another onion-less dinner to complete his redemption with Charter Guests Kenny and Amber. Joao feels betrayed when he overhears Kasey warning Brooke about his flirtatious ways. An argument erupts between Hannah and Conrad over their polar opposite lifestyles.

Hannah and Joao have a miscommunication over a guest excursion; Anastasia is forced to prepare foods that go against her vegan lifestyle for charter guest, the "Queen of Versailles;" June continues to struggle to impress Hannah.

Captain Sandy continues her on-going battle with Sirocco’s anchors, while Joao and Travis continue their deep dive to set the anchors free. Baseball star, Johnny Damon along with his family and friends not only go against the bad weather, but also a feisty neighboring yacht owner. Meanwhile, Aesha and June bond over their mutual losses. And as the guests depart, Sandy is faced with a big complaint making her second guess her decisions.

Captain Sandy finds one of the crew member’s positions redundant. Joao finally confronts Jack on his lack of work ethic giving him an ultimatum. An overwhelmed Anastasia is pushed to her breaking point in the galley, and when Colin learns that someone will have to leave the boat, he makes a bold move.

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.

Baseball legend Johnny Damon comes on board with a group of his rowdiest friends making the crew work double-time. June struggles to keep her radio on, which leaves Hannah frustrated. And Jack and Travis get in hot water with Captain Sandy when they fail to respond to an alarm. As Anastasia gets more comfortable in the galley, questions arise about her food. Jack takes Aesha on a romantic date. Travis and Joao end up on a dangerous mission to rescue the anchor.

Ben is determined to regain his sea legs, but Sirocco’s faulty galley has other plans. Travis’ latest drunken night has Sandy at the end of her rope. Jack ups his romance game by writing poetry for Aesha, while Anastasia’s apathy for her old job is starting make Hannah’s life more difficult. And rough seas puts the boat in a situation that leaves everyone holding on for dear life.

While Danny is away at the hospital, the crew revels in his absence; Jen finally stands up to Bryan; Tiffany's feelings for Ben increase; as one easy-going charter leaves, the crew is blind-sided by a new group of highly demanding guests.

The demanding charter guests extend their stay, and Hannah puts on her best stew face to regain their trust. Julia and Ben have a class war after a miscommunication goes awry. Meanwhile, the Captain gives Danny his phone back, putting Bryan on high-alert. And Ben's friendship with Hannah deepens when he confides in her about his deep-seated issues.

As the guests finally prepare to leave the yacht after their extended stay, Hannah hopes her charm wins them over with a generous tip. Meanwhile, Captain Mark is left with a big decision that will shake up the dynamic of the entire crew after things escalate between Danny, Bobby, and Bryan. On the crew’s night off, Ben and Tiffany take their flirtation to the next level, unbeknownst to Hannah. And Bobby’s plan to bring a date back on the boat backfires in more ways than one.

Captain Sandy becomes frustrated when the deck crew makes a dangerous mistake. While Adam's working relationship with Bugsy grows stronger, tension mounts between him and Hannah. When a guest is involved in a serious accident, Bobby springs to action with his Firefighter/EMT skills. Meanwhile, an overwhelmed Lauren struggles with her responsibilities and questions her future on the boat. And, an argument between two guests has the crew worried about their tip. Finally, a wild night out sparks romance, leaving Malia in the middle of a complicated love triangle between crew members.

Malia, Wes, and Adam find themselves in uncharted emotional territory as news of their love triangle spreads below deck. The Oklahomans return as charter guests keeping the interior on their toes as they struggle to keep up with their demanding requests. Max misses his girlfriend, while Lauren continues to feel the heat as her duties mount. When Adam deliberately goes against a guest's food preferences and his food is sent back, tempers flare in the galley. And, a low blow from Adam about Hannah's job performance puts Bugsy in the middle of their growing animosity towards each other.

Malia and Adam share a romantic moment, but complications arise when she continues to flirt with Wes. The charter guests play dirty as they challenge the Sirocco crew to a relay race. When Hannah finds out Adam intentionally decided to go against the guests' food preferences, the two butt heads once again. Meanwhile, Bugsy feels alienated from the stews as Hannah and Lauren give her the cold shoulder. And when Hannah informs Captain Sandy about Adam's food sabotage, the rebellious chef finds himself in hot water.

Adam's wedgie prank goes awry, and Wes does everything he can to avoid Adam. A one day charter quickly feels like an eternity when a group of eccentric Texans board Sirocco and keep the demands flowing more than the drinks. Meanwhile, Malia gets on Sandy's bad side when she jeopardizes a routine anchor drop. Bugsy and Lauren become disgruntled about the lack of work that Hannah contributes to the interior. And while Bobby and Malia clash over their responsibilities as deckhands, an unexpected and flirtatious friendship develops between former interior rivals.

Hannah and Conrad re-evaluate whether their opposite outlooks on life will be able to coexist off the boat. Brooke and Kasey start to air their grievances over Hannah’s work ethic, while Jamie’s hard work gets recognition. Kasey and Joao resume their friendship, leading Brooke to question his intentions. And when a group of Sandy’s friends charter the yacht, its make or break for Hannah as she puts on her best stew face.

A recording artist charters Sirocco to shoot a music video and uses the crew as her production assistants; Jack begins to develop feelings for Aesha; Colin has a bout with the anchor chain that could leave Sirocco stranded.

Hannah continues to struggle with working under the close eye of Captain Sandy. After a mishap with the anchor, Sandy realizes her new deck crew has a lot to learn if they are going to have a successful charter season. Bobby develops a crush on Malia and rushes to her aid when she suffers a freak accident. As the guests enjoy a uniquely themed dinner, a slip of the tongue by Adam threatens to ruin a carefully planned surprise. And, a wild night of partying leads to a major argument as Bobby clashes with Hannah over interfering with his past relationships.

The rift between Bobby and Hannah grows even wider when Lauren is dragged into a heated debate about the past. A frustrated Bobby calls out Lauren for having an affair with one of his close friends, leaving an emotional Lauren feeling ostracized. Meanwhile, a group of revealing charter guests shed their clothes while the deck crew tries to remain professional. Bugsy learns of a devastating loss back home and must decide whether she should go home or work through her pain. And, a challenging stern tie goes awry as the boat starts drifting into the cliffside potentially leaving the guests safety in jeopardy.

The naked guests distract the crew as they try to stay focused on their jobs. As Hannah and Bobby hash out their differences, Lauren struggles as the tension mounts between her and Bobby. Meanwhile, Bugsy maintains a stiff upper lip as she deals with the loss of her grandmother. And when Captain Sandy joins the guests for dinner, Adam feels the heat as he strives to deliver the perfect meal. On the last day of charter, a massively twisted anchor chain leaves the crew and guests stranded at sea and threatens to sideline the Sirocco for the rest of the charter season.