To flee from a hopeless arranged marriage with the frivolous son of an affluent shipowner, the beautiful and free-spirited Corfiot, Rena Katsarou, summons up the courage to abandon both her family and a pampered life of riches. On the road with nothing more than a ragged outfit and a short-haired periwig, a desperate feminine Rena boldly becomes the gawky and cheerful lad, Pipis, intent on crossing the Ionian Sea to find freedom. However, as fate would have it, Lefteris--an honest fellow traveller and a recently fired young man--becomes Pipis' guardian angel, utterly unaware, though, of Rena's elaborate disguise. Will he ever find out Rena's secret? In the end, can there be a future between a lady and a tramp?