Whether temporally or spatially focussed, nostalgia results from a division between what is longed for and the moment of longing. This article examines this “nostalgia gap” alongside the analogous gap found in representation. The relationship is highlighted via an analysis of “holiday records”, a genre of recordings that became prevalent in the 1960s. The genre intersects with the more familiar genres of exotica, mood music, easy listening and ambient, but is distinguished by its emphasis on a particular form of spatial reminiscence and imagination. Using the example of “April in Portugal”, a song that started life as a Portuguese fado and subsequently became an international hit and mood music staple, I address a set of questions that illustrate the nostalgia gap. What is being remembered or imagined in the song? Can we distinguish between described and prescribed nostalgia? How is saudade, the specifically Portuguese “grammar of nostalgia”, related to nostalgic languages found on other holiday records?