If cities are palimpsests of history, as Andreas Huyssen suggests, the palimpsest posits a cogent epistemological framework. Periodically de-signified and re-signified, connected and also conflictual, transcultural cities productively lend themselves to the modular and stratified palimpsestual approach. Hybrid Trieste is a compelling case in point. An eccentric port city located in a cul-de-sac within the wider Mediterranean basin, Trieste is both peripheral and transcultural: an insular city and palimpsest typified by periodic colliding, breaking, and reconstituting into new forms of syncretic and (a)synchronous cultures and memories. Taking Trieste’s particular Mediterranean identity as a point of departure, the aim of this article is to revisit several memorial sites, both material and symbolic, where the city’s hybrid transcultural memories are mediated and most visibly and productively coalesce. Trieste’s Mediterranean transcultural memories demonstrate the extent to which Trieste inhabits this most elusive interstitial space, and to this day continues to be a powerful generator of memories, myths, and rhetoric.