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.

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.

The Sirocco crew comes to terms with Mila's controversial views. Captain Sandy's good friend, Dr. Jennifer Berman, returns with the expectation of actually leaving the dock this year. Hannah's on high alert making sure Sandy's friends are taken care of and Sandy's toast is butter free. Meanwhile, Joao continues to struggle to motivate Jack. Colin wonders if this new crew might be a little too bawdy for him, and Chef Mila's redemption charter gets off to a choppy start forcing Sandy to think outside the box with a unique plan.

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.

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 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.

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.

Former MLB player Johnny Damon comes on board with a group of rowdy friends; Jack and Travis fail to respond to an alarm; questions arise about Anastasia's food; Jack takes Aesha on a date; Travis and Joao must rescue the anchor.

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.

The crew enjoys a day off at a resort in Monte Carlo, Monaco; Joao and Hannah have a heart to heart; Travis confronts Joao over his treatment of Aesha; Anastasia tries to regain her swagger after poor reviews from the previous charter.

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.

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.

Guests aren't as impressed with Ben's first dinner as he'd hoped; Anastasia struggles to adjust back to her previous role; Travis stews over losing Jack to Aesha; a sudden burst of wind sends the deck team scrambling.

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 writes poetry for Aesha; rough seas has everyone holding on for dear life.

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 prepares for the final charter of the season; with Joao sidelined with a fever, Travis is forced to step up; bad weather rolls into the South of France; when Anastasia gets on Sandy's bad side, Hannah bears the brunt of the captain's fury.

A boat catches fire in port stranding Sirocco with nowhere to go; the interior team resents Sandy's harsh criticism; Jack and Aesha contemplate their future; Sandy calls out Hannah's lack of passion for yachting.