Season 5

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.