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.

Another season in the Mediterranean gets under way as Captain Sandy Yawn and the crew cruise the Italian coast; chef Adam returns and is ready to redeem himself. Returning chief Hannah finds herself at a crossroads on whether she should settle down.

The love triangle intensifies as Joao continues to send mixed messages to both Brooke and Kasey, which prompts them to confront him. A night out at a Michelin-starred restaurant inspires Adam to step up his culinary game for the rest of the season. Conrad’s feelings for Hannah grow stronger while his relationship with Sandy continues to become more strained. Sandy dishes out high praise to Kasey much to the chagrin of Hannah.

While the crew works hard to pull off a magical picnic for the guests on the island of Capri, Joao earns the praise of Captain Sandy for putting out all the water toys as the solo deckie. Later, rough seas force Captain Sandy to maneuver the boat during dinner service to help a sea sick charter guest. After the guests depart, Captain Sandy announces a crew day off and Brooke throws Hannah a fake 30th birthday dock party. During the celebration, the love triangle appears to be tipping in Kasey’s favor forcing Brooke to either take a chance and go for Joao or risk missing out forever.

Joao solidifies the love triangle, leaving Kasey confused. On the crew day off, Hannah feels slighted by Brooke when she pursues a relationship with Joao. Meanwhile, Adam gets ready for his chance at redemption as he goes foraging for food fretting the return of charter guests from last season. Tensions rise when Hannah doesn’t feel supported by Conrad leaving her stricken with anxiety. And, Jamie becomes very ill and Captain Sandy must pull together a charter with one deckhand quarantined and her chief stew down for a mental health day.

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 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.

Hannah and Joao’s contempt for one another grows even stronger when Joao ruffles Hannah’s feathers. And, on the first day of charter, strong winds leave the boat stuck at the dock, and Adam must do everything in his power to keep the guests distracted with his cuisine. Meanwhile, Hannah’s leadership skills are challenged by Brooke and Kasey. And Colin finally gets the nerve to reveal his season-long feelings for Brooke.

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.

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.

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 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.