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.

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.

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.

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.

Anastasia fills in as the temporary chef and Travis helps out as sous chef; the exhausted crew continues to work with a person down in each department; Ashley films her music video; João acts quickly in a dangerous situation involving the anchors.

The crew enjoys a day off at an exclusive resort in Monte Carlo. A new group of energetic charter guests come on board, but when they complain about cold food, Sandy begins to wonder whether Anastasia has what it takes.

Joao confides in Capt. Sandy about his heartbreak; chef Mila continues to struggle; Hannah takes on double duty trying to please unhappy charter guests who teach Travis a valuable lesson -- that there are no pants in the South of France.

The Sirocco braces for its most exclusive charter guest yet -- the Queen of Versailles; Joao faces old demons after a drunken night out as well as an increasingly defiant deck crew; a new third stew joins the boat.

The charter guests request a White Party for their final dinner, and Ben goes to great lengths in creating a menu for the theme. Joao’s ego gets him in hot water with Captain Sandy, while Jack enlists the crew to help him ask Aesha to be his girlfriend. And Hannah’s leadership skills are called into question after Sandy calls out the interior crew for a subpar performance in service.

The crew’s first beach picnic of the season gets off to a very rocky start, ultimately leaving Colin shattered and empty-handed. Meanwhile, Chef Mila faces her biggest challenge yet, baking. And Hannah realizes Mila may not be up to the standard she’s used to. Joao continues to have growing pains in his new leadership position as he attempts to get his deckhand Jack in line.

Ben’s first dinner doesn’t wow the guests as much as he had hoped leaving him questioning if he still has his sea legs. Anastasia has a hard time adjusting back to her old third stew role, while Travis continues to have a difficult time losing Jack to Aesha. And when 20 knots of wind strike, the deck team rushes to secure the vessel leaving Colin in a place which could end his season.

The crew prepares for the final charter of the season, and with Joao sidelined with a high fever, Travis is forced to step up. Bad weather rolls into the South of France leaving Sirocco stuck at the dock, adding more pressure on the interior team to perform. And when Anastasia gets on Sandy’s bad side, Hannah bares the brunt of the Captain’s fury.

The crew comes to terms with Mila's controversial views; Capt. Sandy's friend, Dr. Jennifer Berman, returns with the expectation of leaving the dock this year; Joao struggles to motivate Jack; Colin wonders if the new crew is too bawdy for him.

On the final episode of the season, a boat catches fire in port stranding Sirocco with nowhere to go. The interior team grows resentful of Sandy’s harsh criticisms, while Jack and Aesha contemplate their future off the boat. And Sandy calls out Hannah’s lack of passion for yachting, which leaves both of them wondering if this will be their last charter together.