Join Chef Ben Robinson and eight new crew members as they prepare the Ionian Princess, for a new charter season around the Greek Islands. Fresh faces present new challenges as the crew learns to work and live together while preparing to welcome their first guests. Bosun Bryan gets an unexpected promotion, while chief steward Hannah has her hands full with her ambitious third stew. Trying to meet the guests' one non-negotiable, they run into an unforeseen obstacle: streaming a live football game in the middle of the Mediterranean.

The crew's effort to stream a football game in the middle of the Mediterranean doesn't go as planned, but their efforts don't go unnoticed by the charter guests. Ben redeems himself after the previous night's Moussaka mishaps. Bobby crushes on Julia, and meanwhile a homesick Jen feels like she's getting assigned all of the tedious tasks by Bryan and is being underutilized. And after staying up all night with the Primary's husband, Tiffany breaks down after Hannah confronts her for not finishing her duties.

After the crew's first night off, Hannah puts her foot down when Bobby and Danny bring girls back to the yacht. Bryan attempts to smooth things over with the captain, but the boys are given their first strike. When an all-female group charters the yacht for their upcoming calendar shoot, the Ionian Princess crew struggles to keep up with their demands. As the crew assist the charter guests with their photo shoot, Danny breaks yachtie rule number one and drama ensues.

Danny disobeys a direct order from Captain Mark when he decides to give a love poem to a charter guest. Julia calls her boyfriend in England, while Bobby's feelings for her grow stronger. Ben and Hannah's work relationship has reached smooth sailing, while Tiffany works harder on her stew skills in hopes of Hannah noticing. On their night off, Ben is torn between two stews, but is shocked when he finds one of them in his bunk with Bryan.

After Ben apologizes for shutting down Bryan and Tiffany's fun, the crew prepares for their next charter hailing from Oklahoma. The stews are tasked with putting together a country hoedown complete with bales of hay. Meanwhile, the deck crew unravels when Danny accuses Bobby for not being part of the team. After hours, the charter guests seem to have a threesome in the jacuzzi and once again, Danny is in hot water for overstepping his boundaries.

New charter guests come aboard to celebrate their seven-month dating anniversary, and the crew must provide the romantic trip of their lives. Ben takes Hannah on a date, but a major galley miscommunication during the guests' dinner could tarnish any romantic hope for the two. And, when a nearby vessel begins to sink, the Ionian Princess crew has to spring into action to help save it.

Hannah feels betrayed when Ben goes to the Captain about their galley miscommunication. The Crew finally enjoys a day off until Bryan gives Danny an etiquette lesson. An all-male charter group has Danny and Bobby finding them arm candy in Mykonos.

Hannah's migraine explodes when the charter guests bring back a large group of girls on board. Upon their exit, the bachelors anoint Danny as the charter MVP, much to the chagrin of Bobby and Bryan. And, Danny continues to lose the respect of his crew by breaking yet another yachtie code and inserting himself into Hannah and Ben's business.

Hannah and Ben redefine their relationship, while Bobby realizes he can't shut off his feelings for Julia. After the crew pulls off a beach BBQ, Ben has to make American S'mores in Greece. And Bryan confronts Julia about not completing her duties.

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.

For the final charter, an all-male group brings their own set of demands, and an exhausted crew must struggle to keep up. After weeks of building frustration, the girls band together to confront their First Mate Bryan. Everyone prepares to say goodbye to the Ionian Princess, but not before last minute feelings are revealed and the charter season goes out with a bang.

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 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.

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.

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.

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 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.

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.

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.

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.

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, 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.

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.