Below Deck Mediterranean returns for its fifth season with Captain Sandy Yawn at the helm of the mega-yacht Wellington, cruising one of the most desired yachting locations in the Mediterranean: Mallorca, Spain. After earning the Lead Deckhand title in season 2, Malia returns as Captain 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 while having to overcome Captain Sandy's skepticism from last charter season's galley struggles. Hannah returns as Chief Stew in a new stage of her life, but immediately finds herself challenged by an experienced Second Stew. When the first guests arrive, cracks begin to surface as Hannah attempts to maintain control of her team.

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.

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.

Below Deck Mediterranean returns for its fifth season with Captain Sandy Yawn at the helm of the mega-yacht Wellington, cruising one of the most desired yachting locations in the Mediterranean: Mallorca, Spain. After earning the Lead Deckhand title in season 2, Malia returns as Captain 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 while having to overcome Captain Sandy's skepticism from last charter season's galley struggles. Hannah returns as Chief Stew in a new stage of her life, but immediately finds herself challenged by an experienced Second Stew. When the first guests arrive, cracks begin to surface as Hannah attempts to maintain control of her team.