Alex graduates as valedictorian in glorious rascally style, but during the stunt one last time chases a babysitting au pair, now for Sara. So his stepmother Jenny must do it herself again on Oliver's tropical surprise vacation, with some help from Katie, who is allowed to bring along her study buddy Ariana, to Alexa's taste when they arrive in a Puertorican villa managed by Nigel's brother Rupert. While the girls swoon over local rental bikes entrepreneur Danny, jealous Katie sabotages Alex's buddy romance with Ari, which proves more painful for all of them then dodging the clueless bodyguards. Oliver meanwhile can't escape from the threat posed to his company's future, a water motor, a legacy for Alex incompatible with the heir's artistic ambitions, posed by executive rival Walter Hausen at board level.