This work addresses a particular kind of cross domain personalization task consisting of selecting simultaneously two items in two different domains and recommending them together because they fit the user preferences and also they fit well together. In particular, it is shown that given a personalized recommendation for points of interests (POIs), the user’s selection of POIs can be influenced by enriching their presentation with music tracks that are matching the user’s profile and also the POIs. This paper presents the results of an online, live-users, experiment where we evaluated alternative approaches for matching POIs and music, based on tagging and text matching. Categories and Subject Descriptors H.3.3 [Information Storage and Retrieval]: Information Search and Retrieval; H.3.5 [Information Storage and Retrieval]: On-line Information Services—Web-based services General Terms Algorithms, Design, Experimentation Keywords Recommender Systems, Context, Music Personaliz...