Beginning with playground scenes, Ray Young, accompanied by family members, tours coastal towns in Kent and Sussex. Rye is the first stop followed by Battle Abbey where they enjoy a picnic and explore the ruins. At a cafe in Eastbourne, the boys eat ice-cream with wafers before visiting the shingle beach and later, the sea front gardens. The final stop is at Hastings where they visit the castle high on the cliffs as well as the sea front. We end with views over the seaside town.

Ray Young, who made 'Holiday in May' was an independent amateur filmmaker as well as being an active member of the Eastbourne Cine Group. His films often feature local events in East Sussex including agricultural shows, local craftsmen at work, local lidos and numerous family events. As can be seen in this film, he seemed to be as interested in showing the process of filming as well as the subjects in themselves. The scenes in the children's playground demonstrate his technique.