In this paper we present a Travel Blog Assistant System that facilitates the travel blog writing by automatically selecting for each blog paragraph written by the user the most relevant images from an uploaded image set. In order to do this, the system first automatically adds metadata to the traveler s photos based both on a Generic Visual Categorizer (visual keywords) and by exploiting cross-content web reppositories (textual keywords). The images are then ranked for each blog paragraph based on the similarity between the enriched metada and the given paragraph. The technology developed and presented here has potential beyond travel blogs, which served just as an illustrative example. Clearly, this same methodology can be easily used by professional users in the fields of multimedia document generation and automatic illustration and captioning.