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.

Malia returns as Capt. Sandy's first female bosun, a role she hopes to grow into while commanding respect from her all-male deck team. Brazilian chef Kiko tries to make a good first impression. Hannah is challenged by an experienced Second Stew.

Hannah struggles to get her Second Stew in line, and tensions reach a boiling point when Lara refuses to take direction from Hannah. In the galley, Kiko finds himself up against guests that are less than satisfied. Malia deals with a green deck crew and is forced to draw the line with Pete.

Romance is in bloom on the crew’s first night out of the season, as Pete makes his move while Rob and Jess find themselves connecting on a deeper level. The second charter kicks off when guests with ties to the music industry arrive, but unforeseen circumstances immediately put the Wellington crew behind the eight ball. Meanwhile, Pete’s attitude forces Malia into a difficult confrontation, and tensions between Hannah and Lara take a surprising new turn.

With bad weather rolling in and down her Second Stew, Hannah scrambles to manage the interior with only Jess to rely on. Captain Sandy and Malia draw a hard line with the deck team when they call the guys out for their questionable behavior. Kiko struggles to prepare a picnic lunch for the first off-boat excursion of the season. After surviving the charter, Hannah is rewarded with a Second Stew, but she quickly realizes the newest addition to her team may be more than she bargained for.

A blast from the past returns amidst a massive thunderstorm that threatens to keep The Wellington docked for their next charter. Rob and Jessica deepen their connection, while Pete’s attitude continues to frustrate Malia. Meanwhile, Kiko is pushed to the limit by a group of new guests whose requests are incredibly demanding.

Kiko faces his biggest challenge yet when demanding charter guests invite friends to join a 6-course dinner. Hannah confronts Bugsy about their past, while Rob and Jess find their budding relationship threatened by a new revelation. Meanwhile, an unexpected injury threatens to upend the rest of the charter season.

An injured Jess fights to maintain her spot on the boat, while another crew member’s inappropriate behavior finally catches up to him. Meanwhile, high-maintenance charter guests challenge the interior and expose cracks in Hannah and Bugsy’s relationship. And after surviving a 72-plate dinner last charter, Kiko is faced with something equally challenging and he’s once again put to the test.

After struggling through the first day of charter, Kiko fights to regain his footing with a demanding set of charter guests. While Hannah leans on an overworked Bugsy to carry an injured Jess, Captain Sandy becomes concerned about the interior’s performance. Meanwhile, Malia looks to Rob and Alex to step up after she’s forced to make a tough call that changes the exterior’s dynamic. And a surprise complaint forces Captain Sandy to issue an ultimatum.

On a crew night out, Alex reveals his feelings to Bugsy while Hannah struggles to connect with the group. Meanwhile, Captain Sandy comes down on Jess for her performance in the laundry room, and an incident with the water toys forces Malia into an emergency rescue. With his job on the line, Kiko rallies himself for a successful charter, but a Vegas-themed dinner threatens to unravel everything.

Captain Sandy and Kiko find themselves at a crossroad after a critical dinner, while Hannah fights to maintain control under the weight of a stressful season. On a guest excursion into Valldemossa, Rob and Jess up the ante in their relationship.

The crew enjoys a day off at an exclusive beach club in Mallorca, but concerns arise when Hannah stays behind to nurse an illness. Romance is in the air when Malia’s boyfriend Tom arrives for a visit, while Alex takes stock of his relationship with Bugsy, and Jess offers Rob a bold invitation. With Kiko off the boat, Captain Sandy struggles to find a suitable replacement.

With Hannah’s back against the wall, Captain Sandy faces a difficult decision that could change the trajectory of The Wellington. Bugsy grapples with a new challenge, while Malia worries about Tom’s ability to navigate a chaotic first charter.

Down a stew in the wake of Hannah’s departure, Bugsy fights to keep the interior afloat with a skeptical Jess by her side. Malia struggles to manage a frustrated deck team, while helping Tom navigate his first charter. Finally, the interior team is relieved when a new Second Stew arrives onboard.

Baseball legend Johnny Damon returns to charter in Ibiza, putting pressure on Tom to rectify the Damons’ poor experience with the food they were served last season. With Aesha onboard, Bugsy ups her expectations for the interior team. Meanwhile, Rob’s personal life begins to interfere with his work, and Jess notices some red flags with his behavior.

Jess deals with a scary medical condition; Rob draws Malia's ire by continuing to underperform on deck.

After a tumultuous night in Ibiza, Rob and Jess struggle to reconcile; Capt. Sandy scrambles to avoid a catastrophic disaster; the new charter guests arrange a bet with Bugsy; a guest request sends a sleep-deprived Tom over the edge.

A speedo-clad Bugsy prepares a naughty-themed evening for the guests, while managing the fallout of cucumber-gate. Tensions run high between Captain Sandy and Chef Tom, while Jess becomes wary of Aesha. On a crew night out, Alex questions Bugsy about the direction of their relationship, while Rob and Jess spend a romantic night in the guest cabins. And on the morning of the final charter, a big mistake leaves a crew member ready to walk off the boat.

Tom becomes incensed over a provisioning mishap, while Malia and Bugsy struggle to manage the fallout; Rob and Alex find themselves ogled by the final charter guests of the season; a group photo with Rob and Aesha sends Jess over the edge.

Jess confronts Aesha over the guests’ group photo, while the rest of the boat races to mitigate the impending damage. Tom works to keep a lid on his frustrations, as Malia waits for the other shoe to drop. Meanwhile, Aesha makes a decision about her future and Rob is presented with an alternative to traveling with Jess to Bali.

As the last charter comes to an end, Captain Sandy reckons with a chaotic season while the few remaining chips continue to fall. Rob and Jess struggle to reconcile after a disastrous fight, while Aesha comes to grips with the end of her yachting career. Tom looks to clear his final hurdle, as Alex hopes to leave things with Bugsy on a positive note. On their final night out before parting ways, the crew gets an enormous surprise.

The cast gather online for the reunion; Hannah confronts Captain Sandy Yawn about why she doesn't trust her.

Andy rejoins the Valor crew to go deep discussing Ashton and Kate's terrifying fight, the dysfunctional crew dynamic, and Rhylee's frustrations with the deckhands.