Digitisation of the cultural heritage means that a significant amount of material is now available through online digital library portals. However, the vast quantity of cultural heritage material can also be overwhelming for many users who lack knowledge of the collections, subject knowledge and the specialist language used to describe this content. Search portals often provide little or no guidance on how to find and interpret this information. The situation is very different in museums and galleries where collections are organized in exhibitions which offer themes and stories that visitors can explore. The PATHS project, which is funded under the European Commission's FP7 programme, is developing a system that explores the familiar metaphor of a trail (pathway) to enhance the discovery and use of the content made available in digital libraries. This paper will report on the findings of the user requirements analysis and the specifications for the first prototype of the PATHS system which is based on contents from Europeana and the Alinari Archives.